Incomplete Functionalization of Glycodendrimers: Effects on Binding Affinity with Wheat Germ Agglutinin Takahiko Matsushita; Naomichi Toda; Tetsuo Koyama; Ken Hatano; Koji Matsuoka
European Journal of Medicinal Chemistry Reports,
First page：100266,
Last page：100266, Apr. 2025
Elsevier BV, Scientific journal
DOI：https://doi.org/10.1016/j.ejmcr.2025.100266DOI ID：10.1016/j.ejmcr.2025.100266,
ISSN：2772-4174 Self-Assembly of Silole-Based Aggregation-Induced Emission Compounds with Green Fluorescent Protein under Physiological Conditions for Traceable and Versatile Drug Delivery. Miho Suzuki; Fumihiro Murakami; Md Shazadur Rahman; Yusuke Akui; Ken Hatano
ACS applied bio materials,
Volume：7,
Number：10,
First page：6477,
Last page：6491, Oct. 2024,
［International magazine］Biomacromolecules are viewed as promising drugs due to their specific functions in biological processes, biocompatibility, and pharmacological efficacy. Injective administration, chosen to avoid intestinal barriers, may in turn lead to immediate decay in the circulation system, unreliable targeting performance, or the induction of immune responses. For some biomacromolecules, chemically modified proteins have been developed for practical use. Various cargo or carrier systems are under development but have been delayed by technical difficulties. We present self-assembled nanocapsules with diameters ranging from 100 to 500 nm that can be deployed in physiological buffers to enclose various substances present in the buffers at the same time. Our amphiphilic nanocapsule, consisting of silole-core dendrimer products as the hydrophobic part and green fluorescent protein (GFP) derivatives as the hydrophilic part, connects and assembles spontaneously when mixed in solutions while engulfing dissolved or dispersed compounds together in a dose-dependent manner and shows unique optical characteristics because the dendrimer products exhibit aggregation-induced emission. Furthermore, the emission of the dendrimer causes considerable fluorescence resonance energy transfer (FRET) to GFP derivatives upon association. We could easily monitor assemblies by FRET states and particle sizes and have confirmed a stable presence in the buffer for at least a month. Further tracking of nanocapsules by fluorescence confirmed efficient uptake into some cancer cells. Nanocapsules based on GFP variants with or without a cell-surface-specific tag demonstrated that the tag improved the potential for specific targeted delivery. There were also indications that the nanocapsules became unstable after cellular uptake in the intracellular environment. We report here the simple preparation of traceable, stable, and biocompatible self-assembled nanocapsules as the basis for a versatile drug delivery system.
English, Scientific journal
DOI：https://doi.org/10.1021/acsabm.4c00639DOI ID：10.1021/acsabm.4c00639,
PubMed ID：39256188 Interpenetrating Polymer Network Capturing FRET-Sensitive Polymers Available for an Enzyme Assay Kota Miyairi; Hirokatsu Arai; Takahiko Matsushita; Tetsuo Koyama; Ken Hatano; Koji Matsuoka
Biomacromolecules, Aug. 2024,
[Reviewed]English, Scientific journal
DOI：https://doi.org/10.1021/acs.biomac.4c00622DOI ID：10.1021/acs.biomac.4c00622,
ORCID：164775308 Use of an oxazolidinone derivative of a sialyl thioglycoside as a useful glycosyl donor for α-favorable glycosidation with simple alcohols Jianhong Zhang; Tetsuo Koyama; Takahiko Matsushita; Ken Hatano; Koji Matsuoka
Tetrahedron Letters, Aug. 2024,
[Reviewed]English, Scientific journal
DOI：https://doi.org/10.1016/j.tetlet.2024.155189DOI ID：10.1016/j.tetlet.2024.155189,
ORCID：163137912 Preparation of fluorogenic glycopolymers having mannose moieties that can be used for determining the affinity of lectins by means of intermolecular FRET Kota Miyairi; Takahiko Matsushita; Tetsuo Koyama; Ken Hatano; Koji Matsuoka
Journal of Molecular Structure, Jun. 2024,
[Reviewed]English, Scientific journal
DOI：https://doi.org/10.1016/j.molstruc.2024.137896DOI ID：10.1016/j.molstruc.2024.137896,
ISSN：0022-2860,
ORCID：162952645 pH-Dependent proteolytic activity of histidine-pendant polyacrylamides Shinzo Omiya; Hinako Yamochi; Tetsuo Koyama; Ken Hatano; Koji Matsuoka; Takahiko Matsushita
European Polymer Journal, Apr. 2024,
[Reviewed]English, Scientific journal
DOI：https://doi.org/10.1016/j.eurpolymj.2024.112898DOI ID：10.1016/j.eurpolymj.2024.112898,
ISSN：0014-3057,
ORCID：162952627 Preparation of a water-soluble polymer having pheophorbide a side chains using glycopolymer assembly Koji Matsuoka; Jyuichi Nakada; Masataka Nakazato; Takahiko Matsushita; Tetsuo Koyama; Ken Hatano
Tetrahedron Letters, Mar. 2024,
[Reviewed]English, Scientific journal
DOI：https://doi.org/10.1016/j.tetlet.2024.154963DOI ID：10.1016/j.tetlet.2024.154963,
ISSN：0040-4039,
ORCID：162952664 Synthetic assembly of α-O-linked-type GlcNAc using polymer chemistry affords sugar clusters, which effectively bind to lectins Jyuichi Nakada; Takahiko Matsushita; Tetsuo Koyama; Ken Hatano; Koji Matsuoka
Bioorganic & Medicinal Chemistry Letters, Feb. 2024,
[Reviewed]English, Scientific journal
DOI：https://doi.org/10.1016/j.bmcl.2024.129616DOI ID：10.1016/j.bmcl.2024.129616,
ISSN：0960-894X,
ORCID：162952363 Preparation of N-Linked-Type GlcNAc Monomers for Glycopolymers and Binding Specificity for Lectin Takahiko Matsushita; Momoka Nozaki; Mio Sunaga; Tetsuo Koyama; Ken Hatano; Koji Matsuoka
ACS Omega, Oct. 2023,
[Reviewed]English, Scientific journal
DOI：https://doi.org/10.1021/acsomega.3c05151DOI ID：10.1021/acsomega.3c05151,
ISSN：2470-1343,
ORCID：162952808 Preparation of a Water-Soluble Glycopolymer Bearing Porphyrin Skeletons and Its Biological Properties Yoshihiro Ishimaru; Tomohide Moteki; Miho Suzuki; Tetsuo Koyama; Takahiko Matsushita; Ken Hatano; Koji Matsuoka
ACS Omega, Oct. 2023,
[Reviewed]English, Scientific journal
DOI：https://doi.org/10.1021/acsomega.3c05581DOI ID：10.1021/acsomega.3c05581,
ISSN：2470-1343,
ORCID：162953065 Proteolytic polymer: polyacrylamides functionalized with amino acids cleave bovine and human serum albumins Takahiko Matsushita; Hinako Yamochi; Shinzo Omiya; Tetsuo Koyama; Ken Hatano; Koji Matsuoka
Bioorganic & Medicinal Chemistry,
Volume：92,
First page：117422,
Last page：117422, Sep. 2023
Elsevier BV, Scientific journal
DOI：https://doi.org/10.1016/j.bmc.2023.117422DOI ID：10.1016/j.bmc.2023.117422,
ISSN：0968-0896 Synthetic assembly of a series of glycopolymers having sialyl α2-3 lactose moieties connected with longer spacer arms Ryota Adachi; Takahiko Matsushita; Tetsuo Koyama; Ken Hatano; Koji Matsuoka
Bioorganic & Medicinal Chemistry,
Volume：81,
First page：117209,
Last page：117209, Mar. 2023,
[Reviewed]Elsevier {BV}, English, Scientific journal
DOI：https://doi.org/10.1016/j.bmc.2023.117209DOI ID：10.1016/j.bmc.2023.117209,
ISSN：0968-0896,
ORCID：129064751 Dendritic maleimide-thiol adducts carrying pendant glycosides as high-affinity ligands Takahiko Matsushita; Naomichi Toda; Tetsuo Koyama; Ken Hatano; Koji Matsuoka
Bioorganic Chemistry,
Volume：128,
First page：106061,
Last page：106061, Nov. 2022
Elsevier BV, Scientific journal
DOI：https://doi.org/10.1016/j.bioorg.2022.106061DOI ID：10.1016/j.bioorg.2022.106061,
ISSN：0045-2068 Chemical modification of CNN 1. Complete protection of CNN Koji Matsuoka; Daiki Endo; Ryota Adachi; Tetsuo Koyama; Takahiko Matsushita; Ken Hatano
Tetrahedron Letters,
Volume：103,
First page：153986,
Last page：153986, Aug. 2022
Elsevier {BV}, English, Scientific journal
DOI：https://doi.org/10.1016/j.tetlet.2022.153986DOI ID：10.1016/j.tetlet.2022.153986,
ISSN：0040-4039,
ORCID：116408632 Quick and ultra-sensitive digital assay of influenza virus using sub-picoliter microwells. Hiroki Ashiba; Masato Yasuura; Takashi Fukuda; Ken Hatano; Makoto Fujimaki
Analytica chimica acta,
Volume：1213,
First page：339926,
Last page：339926, Jun. 2022,
［International magazine］Quick and sensitive virus detection methods have been developed using sub-picoliter microwells. One method uses an aggregation-induced emission (AIE) reagent, and the other uses an enzymatic reaction supported with immunomagnetic beads at a high concentration of 108 particles/mL. Examination of influenza A virus detection using the AIE reagent exhibited a detection limit of 3 × 105 copies/mL, which was achievable within 1 min of the total measurement time. The high-concentration immunomagnetic beads method exhibited a detection limit as low as 1 × 102 copies/mL. The developed methods are effective and practical tools for ultrafast and ultrasensitive virus detection.
English, Scientific journal
DOI：https://doi.org/10.1016/j.aca.2022.339926DOI ID：10.1016/j.aca.2022.339926,
PubMed ID：35641063 Systematic synthesis of a series of glycopolymers having N-acetyl-D-glucosamine moieties that can be used for evaluations of lectin—carbohydrate interactions Koji Matsuoka; Masaki Nakagawa; Tetsuo Koyama; Takahiko Matsushita; Ken Hatano
European Polymer Journal,
Volume：168,
First page：111101,
Last page：111101, Apr. 2022
Elsevier BV, Scientific journal
DOI：https://doi.org/10.1016/j.eurpolymj.2022.111101DOI ID：10.1016/j.eurpolymj.2022.111101,
ISSN：0014-3057 Preparation of glycopolymers having sialyl α2 → 3 lactose moieties as the potent inhibitors for mumps virus Koji Matsuoka; Takayuki Kaneshima; Ryota Adachi; Jiei Sasaki; Takao Hashiguchi; Tetsuo Koyama; Takahiko Matsushita; Ken Hatano
Bioorganic & Medicinal Chemistry Letters,
Volume：52,
First page：128389,
Last page：128389, Nov. 2021
Elsevier BV, Scientific journal
DOI：https://doi.org/10.1016/j.bmcl.2021.128389DOI ID：10.1016/j.bmcl.2021.128389,
ISSN：0960-894X Preparation of lauryl thioglycoside of N-glycolylneuraminic acid (Neu5Gc) as a useful glycosyl donor for assembly of an oligosaccharide containing Neu5Gc Jianhong Zhang; Tetsuo Koyama; Takahiko Matsushita; Ken Hatano; Koji Matsuoka
Tetrahedron Letters,
Volume：83,
First page：153403,
Last page：153403, Oct. 2021
Elsevier BV, Scientific journal
DOI：https://doi.org/10.1016/j.tetlet.2021.153403DOI ID：10.1016/j.tetlet.2021.153403,
ISSN：0040-4039 Controlled release of molasses melanoidin-like product from hybrid organic-inorganic silica xerogels and its application to the phytoextraction of lead through the Indian mustard Ken-ichi Hatano; Minori Teraki; Daiki Nakajima; Takeshi Yamatsu
ENVIRONMENTAL SCIENCE AND POLLUTION RESEARCH,
Volume：28,
Number：28,
First page：37562,
Last page：37569, Jul. 2021
In this study, we investigate the release of melanoidin-like product (MLP) from hybrid silica xerogels to control the quantity of MLP in the medium for lead phytoextraction. In the preparation of the hybrid organic-inorganic xerogels with MLP, tetraethoxysilane (TEOS), methyltriethoxysilane (MTES), propyltriethoxysilane (PTES), and 3-aminopropyltriethoxysilane (APTES) were used as precursors. The experimental results suggest that the release of MLP can be easily controlled by partially substituting TEOS with the organosilanes. The addition of the organosilanes lowered the release rate of MLP in the following order of xerogels: TEOS, MTES/TEOS, PTES/TEOS, and APTES/TEOS. Furthermore, a novel phytoextraction of lead through the Indian mustard was conducted using the MLP-doped TEOS xerogel. Results show that the addition of TEOS xerogel did not have any influence on the growth of the mustard, whereas the lead uptake significantly increased in a nutrition medium with 1-mM Pb(NO3)(2). In conclusion, the beneficial effect of the MLP-doped TEOS xerogel on lead phytoextraction was confirmed.
SPRINGER HEIDELBERG, English, Scientific journal
DOI：https://doi.org/10.1007/s11356-021-13363-1DOI ID：10.1007/s11356-021-13363-1,
ISSN：0944-1344,
eISSN：1614-7499,
Web of Science ID：WOS:000628491500008 Verification of suitable ratio of carbohydrate residues in a glycopolymer having GlcNAc moieties for determining the affinity for wheat germ agglutinin Koji Matsuoka; Shohei Yamashita; Tetsuo Koyama; Takahiko Matsushita; Ken Hatano
Journal of Molecular Structure,
Volume：1217,
First page：128404,
Last page：128404, Oct. 2020
Elsevier BV, Scientific journal
DOI：https://doi.org/10.1016/j.molstruc.2020.128404DOI ID：10.1016/j.molstruc.2020.128404,
ISSN：0022-2860 Fluorogenic glycopolymers available for determining the affinity of lectins by intermolecular FRET Koji Matsuoka; Yuya Suzuki; Tetsuo Koyama; Takahiko Matsushita; Ken Hatano
Bioorganic & Medicinal Chemistry Letters,
Volume：30,
Number：8,
First page：127024,
Last page：127024, Apr. 2020
Elsevier BV, Scientific journal
DOI：https://doi.org/10.1016/j.bmcl.2020.127024DOI ID：10.1016/j.bmcl.2020.127024,
ISSN：0960-894X Neuraminidase-triggered activation of prodrug-type substrate of 4-nitroaniline Takahiko Matsushita; Monique Nami Danyel; Tetsuo Koyama; Ken Hatano; Koji Matsuoka
Bioorganic & Medicinal Chemistry Letters,
Volume：30,
Number：2,
First page：126883,
Last page：126883, Jan. 2020
Elsevier BV, Scientific journal
DOI：https://doi.org/10.1016/j.bmcl.2019.126883DOI ID：10.1016/j.bmcl.2019.126883,
ISSN：0960-894X Simultaneous suppression of magnetic nanoscale powder and fermented bark amendment for arsenic and cadmium uptake by radish sprouts grown in agar medium Xiaotong Sun; Huijiao Mo; Ken-ichi Hatano; Hideyuki Itabashi; Masanobu Mori
ENVIRONMENTAL SCIENCE AND POLLUTION RESEARCH,
Volume：26,
Number：14,
First page：14483,
Last page：14493, May 2019
In this study, we effectively suppressed arsenic and cadmium uptake into a plant using magnetic nanoparticle powder (MNP) and fermented bark amendment (FBA) in agar medium. The MNP (which consists of FeO Fe 2O3) quantitatively adsorbed arsenite (As(III)) and the FBA (which mainly consists of bark waste) adsorbed cadmium, regardless of the pH. The properties of MNP and FBA in agar medium were compared based on the amounts of arsenic and cadmium in cultivated radish sprouts. While adding FBA selectively suppressed cadmium uptake by radishes, adding MNP suppressed the uptake of both arsenic and cadmium. Considering that the uptake of analytes was slightly reduced even in agar without any additives, the agar itself might also have contributed to the suppression of analyte uptake into plants. In addition, even when radish sprouts were cultivated in agar containing arsenic and cadmium (100g/L each) mixed with 25g MNP and 1.25g FBA per 25mL agar, arsenic and cadmium absorption decreased by 90% and 82%, respectively, versus agar without additives. Furthermore, adding the mixed amendment to agar accelerated the growth of radishes, whereas MNP significantly inhibited radish growth even though it reduced analyte uptake. Our results indicated that mixing inorganic and organic adsorbents could simultaneously inhibit cadmium and arsenic uptake by plants and accelerate plant growth in the cadmium and arsenic-contaminated agar medium.
SPRINGER HEIDELBERG, English, Scientific journal
DOI：https://doi.org/10.1007/s11356-019-04756-4DOI ID：10.1007/s11356-019-04756-4,
ISSN：0944-1344,
eISSN：1614-7499,
Web of Science ID：WOS:000466906000073 A constraint scaffold enhances affinity of a bivalent N-acetylglucosamine ligand against wheat germ agglutinin Takahiko Matsushita; Koji Tsuchibuchi; Tetsuo Koyama; Ken Hatano; Koji Matsuoka
Bioorganic & Medicinal Chemistry Letters,
Volume：28,
Number：10,
First page：1704,
Last page：1707, Apr. 2018,
[Reviewed]English, Scientific journal
DOI：https://doi.org/10.1016/j.bmcl.2018.04.047DOI ID：10.1016/j.bmcl.2018.04.047 Iodoacetyl-functionalized pullulan: A supplemental enhancer for single-domain antibody-polyclonal antibody sandwich enzyme-linked immunosorbent assay for detection of survivin Takahiko Matsushita; Hidenao Arai; Tetsuo Koyama; Ken Hatano; Naoto Nemoto; Koji Matsuoka
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS,
Volume：27,
Number：21,
First page：4844,
Last page：4848, Nov. 2017,
[Reviewed]Survivin, an inhibitor of the apoptosis protein family, is a potent tumor marker for diagnosis and prognosis. The enzyme-linked immunosorbent assay (ELISA) is one of the methods that has been used for detection of survivin. However, ELISA has several disadvantages caused by the use of conventional antibodies, and we have therefore been trying to develop a novel ELISA system using camelid single-domain antibodies (VHHs) as advantageous replacements. Here we report a supplemental approach to improve the VHH-polyclonal antibody sandwich ELISA for survivin detection. Iodoacetyl-functionalized pullulan was synthesized, and its thiol reactivity was characterized by a model reaction with L-cysteine. The thiophilic pullulan was applied to an immunoassay as an additive upon coating of standard assay plates with an anti-survivin VHH fusion protein with C-terminal cysteine. The results showed that the mole ratio of the additive to VHH had a significant effect on the consequent response. Mole ratios of 0.07, 0.7, and 7 led to 90% lower, 15% higher, and 69% lower responses, respectively, than the response of a positive control in which no additive was used. The background levels observed in any additive conditions were as low as that of a negative control lacking both VHH and the additive. These results indicate the applicability of the thiol-reactive pullulan as a response enhancer to VHH-based ELISA. (C) 2017 Elsevier Ltd. All rights reserved.
PERGAMON-ELSEVIER SCIENCE LTD, English, Scientific journal
DOI：https://doi.org/10.1016/j.bmcl.2017.09.045DOI ID：10.1016/j.bmcl.2017.09.045,
ISSN：0960-894X,
eISSN：1464-3405,
ORCID：37252279,
Web of Science ID：WOS:000413998900013 Synthetic Assembly of Mannose Moieties Using Polymer Chemistry and the Biological Evaluation of Its Interaction towards Concanavalin A Deepti Diwan; Kohei Shinkai; Toshihiro Tetsuka; Bin Cao; Hidenao Arai; Tetsuo Koyama; Ken Hatano; Koji Matsuoka
MOLECULES,
Volume：22,
Number：1, Jan. 2017,
[Reviewed]Protein-carbohydrate interactions exhibit myriad intracellular recognition events, so understanding and investigating their specific interaction with high selectivity and strength are of crucial importance. In order to examine the effect of multivalent binding on the specificity of protein-carbohydrate interactions, we synthesized mannose glycosides as a novel type of glycosylated monomer and glycopolymers of polyacrylamide derivatives with -mannose (-Man) by radical polymerization and monitored their strength of interaction with concanavalin A (Con A) by surface plasmon resonance (SPR) detection. In a quantitative test using the Con A-immobilized sensor surface, the kinetic affinity for the synthesized polymers, 8a (K-D = 3.3 x 10(-6) M) and 8b (K-D = 5.3 x 10(-5) M), were concentration-dependent, showing strong, specific molecular recognition abilities with lectin. Our study showed the enhancement in recognition specificity for multivalent saccharides, which is often mediated by cell surface carbohydrate-binding proteins that exhibit weak affinity and broad specificity for the individual ligands.
MDPI AG, English, Scientific journal
DOI：https://doi.org/10.3390/molecules22010157DOI ID：10.3390/molecules22010157,
ISSN：1420-3049,
ORCID：41456981,
Web of Science ID：WOS:000395473500154 Synthetic assembly of novel avidin-biotin-GlcNAc (ABG) complex as an attractive bio-probe and its interaction with wheat germ agglutinin (WGA) Amrita Kumari; Tetsuo Koyama; Ken Hatano; Koji Matsuoka
BIOORGANIC CHEMISTRY,
Volume：68,
First page：219,
Last page：225, Oct. 2016,
[Reviewed]A tetravalent GlcNAc pendant glycocluster was constructed with terminal biotin through C-6 linker. To acquire the multivalent carbohydrate-protein interactions, we synthesized a glycopolymer of tetrameric structure using N-acetyl-D-glucosamine (GlcNAc) as the target carbohydrate by the use of 4-(4,6-dime thoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM) as coupling reagent, followed by biotin-avidin complexation leading to the formation of glycocluster of avidin-biotin-GlcNAc conjugate (ABG complex). The dynamic light scattering (DLS) system was implied for size detection and to check the binding affinity of GlcNAc conjugate with a WGA lectin we use fluorometric assay by means of specific excitation of tryptophan at lambda(ex) 295 nm and it was found to be very high K-a similar to 1.39 x 10(7) M-1 in case of ABG complex as compared to GlcNAc only K-a similar to 1.01 x 10(4) M-1 with the phenomenon proven to be due to glycocluster effect. (C) 2016 Elsevier Inc. All rights reserved.
ACADEMIC PRESS INC ELSEVIER SCIENCE, English, Scientific journal
DOI：https://doi.org/10.1016/j.bioorg.2016.08.002DOI ID：10.1016/j.bioorg.2016.08.002,
ISSN：0045-2068,
eISSN：1090-2120,
ORCID：41456984,
Web of Science ID：WOS:000387978400022 Triphenylphosphinecarboxamide: An Effective Reagent for the Reduction of Azides and Its Application to Nucleic Acid Detection Hisao Saneyoshi; Tatsuya Ochikubo; Takushi Mashimo; Ken Hatano; Yoshihiro Ito; Hiroshi Abe
ORGANIC LETTERS,
Volume：16,
Number：1,
First page：30,
Last page：33, Jan. 2014,
[Reviewed]A series of triphenylphosphinecarboxamide (TPPc) derivatives were designed and synthesized as alternative reagents to triphenylphosphine for the facile reduction of azides. The TPPc derivatives performed as efficient reducing agents for the synthesis of primary amines without the need for an additional hydrolysis procedure. The TPPc derivatives were also applied to nucleic acid sensing using a RhAz-oligonucleotide conjugate in a DNA-templated fluorogenic reaction.
AMER CHEMICAL SOC, English, Scientific journal
DOI：https://doi.org/10.1021/ol402832wDOI ID：10.1021/ol402832w,
ISSN：1523-7060,
eISSN：1523-7052,
Web of Science ID：WOS:000329472800009 Use of chloromethylstyrene as a supporter for convenient preparation of carbohydrate monomer and glycopolymers Matsuoka Koji; Kurita Anna; Koyama Tetsuo; Hatano Ken
Carbohydrate Polymers,
Volume：107,
First page：209,
Last page：213, 2014,
[Reviewed]DOI：https://doi.org/10.1016/j.carbpol.2014.01.104DOI ID：10.1016/j.carbpol.2014.01.104,
ORCID：41456992,
Web of Science ID：WOS:000335103900027 Synthesis of chiral dopants based on carbohydrates Tsuruta Toru; Koyama Tetsuo; Yasutake Mikio; Hatano Ken; Matsuoka Koji
Carbohydrate Research,
Volume：393,
First page：15,
Last page：22, 2014,
[Reviewed]DOI：https://doi.org/10.1016/j.carres.2014.04.007DOI ID：10.1016/j.carres.2014.04.007,
ORCID：41456991,
Web of Science ID：WOS:000338714300003 Synthesis and Influenza Virus Inhibitory Activities of Carbosilane Dendrimers Peripherally Functionalized with Hemagglutinin-Binding Peptide Hatano Ken; Matsubara Teruhiko; Muramatsu Yosuke; Ezure Masakazu; Koyama Tetsuo; Matsuoka Koji; Kuriyama Ryunosuke; Kori Haruka; Sato Toshinori
Journal of Medicinal Chemistry,
Volume：57,
Number：20,
First page：8332,
Last page：8339, 2014,
[Reviewed]DOI：https://doi.org/10.1021/jm5007676DOI ID：10.1021/jm5007676,
ORCID：41456989,
Web of Science ID：WOS:000343740700011 Synthesis and Structural Revision of a Brominated Sesquiterpenoid, Aldingenin C Takahashi Shunya; Yasuda Masayuki; Nakamura Takemichi; Hatano Ken; Matsuoka Koji; Koshino Hiroyuki
Journal of Organic Chemistry,
Volume：79,
Number：19,
First page：9373,
Last page：9380, 2014,
[Reviewed]DOI：https://doi.org/10.1021/jo501228vDOI ID：10.1021/jo501228v,
ORCID：40436750,
Web of Science ID：WOS:000342719600044 Improved Signal-to-Noise Ratio of Green-Sensitive Organic Photoconductive Device by Doping Silole Derivative Takeshi Fukuda; Sho Kimura; Norihiko Kamata; Keita Mori; Ken Hatano
MOLECULAR CRYSTALS AND LIQUID CRYSTALS,
Volume：578,
Number：1,
First page：119,
Last page：126, Sep. 2013,
[Reviewed]A signal-to-noise ratio (S/N) is an important factor for an organic image sensor. We investigated the doping effect of silole derivative in the green-sensitive organic photoconductive device for improving S/N. The maximum S/N of 12 was achieved when 1,1-dimethyl-2,5-bis(N,N-dimethylaminophenyl)-3,4-diphenylsilole with the lowest ionization potential was used as an active layer. In addition, the graphene oxide (GO) layer was found to be an important role for decreasing the dark current density, resulting in the high S/N. The maximum S/N of approximately 20 was realized by inserting the GO layer between an indium tin oxide (ITO) anode and an active layer.
TAYLOR & FRANCIS LTD, English, Scientific journal
DOI：https://doi.org/10.1080/15421406.2013.804784DOI ID：10.1080/15421406.2013.804784,
ISSN：1542-1406,
eISSN：1563-5287,
Web of Science ID：WOS:000323813500019 Synthesis of a nucleoside phosphorodithioate analogue responsive to microenvironmental changes through chiral induction Hisao Saneyoshi; Takushi Mashimo; Ken Hatano; Yoshihiro Ito; Hiroshi Abe
TETRAHEDRON LETTERS,
Volume：54,
Number：9,
First page：1080,
Last page：1083, Feb. 2013,
[Reviewed]We have synthesized a 2'-aminomethyl branched-chain sugar nucleoside phosphorodithioate from 2,2'-anhydro uridine and subjected the material to a subsequent cyclization reaction under aqueous conditions using bi-functional linkers. The rate of the cyclization reaction was dependent on the leaving group on the bi-functional linkers. The generation of a chiral phosphorous peak from the achiral precursor, as indicated by P-31 NMR, was identified as a good indicator for potentially probing the local and global features of the DNA structure. (C) 2012 Elsevier Ltd. All rights reserved.
PERGAMON-ELSEVIER SCIENCE LTD, English, Scientific journal
DOI：https://doi.org/10.1016/j.tetlet.2012.12.028DOI ID：10.1016/j.tetlet.2012.12.028,
ISSN：0040-4039,
Web of Science ID：WOS:000315063700010 Convenient assembly of trimeric Le(x) determinants using carbosilane scaffolds by means of Huisgen cycloaddition Koji Matsuoka; Hiroki Yamaguchi; Tatsuya Kohzu; Jun-Ichi Sakamoto; Tetsuo Koyama; Ken Hatano; Shigeto Yamamoto; Tsutomu Mori; Kenichi Hatanaka
TETRAHEDRON LETTERS,
Volume：53,
Number：50,
First page：6793,
Last page：6796, Dec. 2012,
[Reviewed]The Le(x) glycoside having an N-3 moiety at the omega position, which was prepared by using living cells from GlcNAcO(CH2)(12)N-3 as a starting material, was efficiently introduced into a trivalent-type carbosilane core scaffold by means of Huisgen cycloaddition reaction to yield the corresponding glycocluster having three Le(x) moieties at each end. Structural elucidation of the product was performed by a combination of NMR and mass spectroscopic analyses, and the results of the analyses supported the structure of the glycocluster. Evaluation of the glycocluster was carried out using Lotus lectin as a model lectin. Environmental changes of tryptophan residues located at or near the binding sites of Lotus lectin caused fluorescence intensity change. (C) 2012 Elsevier Ltd. All rights reserved.
PERGAMON-ELSEVIER SCIENCE LTD, English, Scientific journal
DOI：https://doi.org/10.1016/j.tetlet.2012.10.004DOI ID：10.1016/j.tetlet.2012.10.004,
ISSN：0040-4039,
ORCID：41457001,
Web of Science ID：WOS:000311473500016 Improved optical-to-electrical conversion efficiency by doping silole derivative with low ionization potential Takeshi Fukuda; Sho Kimura; Zentaro Honda; Norihiko Kamata; Keita Mori; Ken Hatano
PHYSICA STATUS SOLIDI A-APPLICATIONS AND MATERIALS SCIENCE,
Volume：209,
Number：11,
First page：2324,
Last page：2329, Nov. 2012,
[Reviewed]In this paper, we investigated photoconductive characteristics of blue-sensitive organic photoconductive devices with different silole derivatives. A most important finding is that an external quantum efficiency (EQE) increased with decreasing ionization potential of silole derivative. The significant improved EQE can be explained by the dislocation efficiency of photogenerated carriers in the organic layer, which is estimated from the photoluminescence (PL) quantum yield. A maximum EQE of 52% at -26 MV m(-1) was obtained by optimizing the molecular structure and the concentration of silole derivative. This value is the highest EQE for the reported solution-processed blue-sensitive organic photoconductive device. Another interesting result is that the signal-to-noise ratio was drastically improved by doping silole derivative. (C) 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
WILEY-V C H VERLAG GMBH, English, Scientific journal
DOI：https://doi.org/10.1002/pssa.201228242DOI ID：10.1002/pssa.201228242,
ISSN：1862-6300,
Web of Science ID：WOS:000313729800040 A carbosilane dendrimer and a silacyclopentadiene analog carrying peripheral lactoses as drug-delivery systems Hiroaki Aizawa; Kentaro Otomo; Nobuaki Honsho; Tomoyuki Shimazaki; Masumi Villeneuve; Koji Matsuoka; Ken Hatano; Daiyo Terunuma
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS,
Volume：22,
Number：10,
First page：3564,
Last page：3566, May 2012,
[Reviewed]A carbosilane dendrimer (4a) and its silacyclopentadiene analog (4b), both functionalized with lactoses, were tested for their abilities to act as drug-delivery systems. The critical micelle concentrations of 4a and 4b were measured using the drop-volume method in water and were 1.7 and 2.9 mu M, respectively, suggesting that they could act as aggregates of glycoclusters. The amounts of the hydrophobic dye Orange OT loaded onto aqueous micelles of 4a and 4b and the stabilities of the dye/micelle complexes were determined by extracting the dyes from the complexes into chloroform. The particle sizes were measured for the loaded micelles by dynamic light scattering. Transfer of the dye from the micelles to peanut agglutinin was observed by fluorescence microscopy. Given the abilities of micelles of 4a and 4b to bind and release Orange OT, these glycocluster micelles may find use as drug-delivery systems. (C) 2012 Elsevier Ltd. All rights reserved.
PERGAMON-ELSEVIER SCIENCE LTD, English, Scientific journal
DOI：https://doi.org/10.1016/j.bmcl.2012.03.034DOI ID：10.1016/j.bmcl.2012.03.034,
ISSN：0960-894X,
ORCID：41456999,
Web of Science ID：WOS:000303545900035 Lectin Detection Based on the Aggregation-Induced Emission Effect Ken Hatano; Koji Matsuoka; Daiyo Terunuma
TRENDS IN GLYCOSCIENCE AND GLYCOTECHNOLOGY,
Volume：24,
Number：136,
First page：78,
Last page：94, Mar. 2012,
[Reviewed]Effective tests for detecting a virus are important because of the increased risk of exposure to newly emerging and highly infectious pathogens due to global warming and increasing international travel. Time-consuming and highly sensitive methods for detection enable a pathogen to be detected during the early phase of infection; however, simple and quick detection testing that can be performed anywhere is often required, particularly in the case of high infectability and mortal diseases. In this review, we introduce a synthetic approach and optical property of a novel lectin detection utilizing carbohydrate-protein-specific recognition and aggregation-induced emission effect though a few examples and also discuss the emission mechanism.
GAKUSHIN PUBL CO, English
DOI：https://doi.org/10.4052/tigg.24.78DOI ID：10.4052/tigg.24.78,
ISSN：0915-7352,
ORCID：41457005,
Web of Science ID：WOS:000305623400003 Synthetic Assembly of Bifluorescence-Labeled Glycopolymers as Substrates for Assaying alpha-Amylase by Resonance Energy Transfer Koji Matsuoka; Hirokatsu Arai; Hiroyuki Oka; Tetsuo Koyama; Ken Hatano
ACS MACRO LETTERS,
Volume：1,
Number：2,
First page：266,
Last page：269, Feb. 2012,
[Reviewed]To meet the need for a convenient substrate for sensitive and continuous assay for alpha-amylase, we developed a fluorescence resonance energy transfer (FRET)-based polymer substrate. Radical copolymerization of FRET-component monomers in different ratios of fluorogenic donor and acceptor was utilized to prepare such polymers. A glycomonomer as a fluorogenic donor was derived from naphthylmethylated maltotetraose, and a dansyl derivative monomer was used as an acceptor. Their mixture and acryl amide were copolymerized in a typical radical polymerization to yield a bifluorescence-labeled polymer in good yield. All of the polymers showed effective FRET and were used for the continuous assay, of human salivary alpha-amylase. The time course of alpha-amylase reactions led to the apparent kinetic parameters of K-m = 4 mu M and V-max = 0.29 nmol/min. The results strongly suggested that FRET-sensitive polymers are conveniently accessible and applicable for the sensitive determination of biochemical events.
AMER CHEMICAL SOC, English, Scientific journal
DOI：https://doi.org/10.1021/mz200135yDOI ID：10.1021/mz200135y,
ISSN：2161-1653,
ORCID：41457007,
Web of Science ID：WOS:000301969500003 Doping Effect of Silole Derivative in Coumarin 30 Photoconductive Film Toshikatsu Sakai; Hokuto Seo; Satoshi Aihara; Misao Kubota; Norifumi Egami; Keita Mori; Takeshi Fukuda; Ken Hatano; Norihiko Kamata
MOLECULAR CRYSTALS AND LIQUID CRYSTALS,
Volume：568,
First page：74,
Last page：81, 2012,
[Reviewed]To obtain a highly sensitive and color selective photodetector for an image sensor, silole-derivative-doped coumarin 30 photoconductive films were fabricated. The silole-doped films showed excellent color selectivites only in the blue region of visible light. The dark current in the films decreased when the silole-doping concentration was increased, which reached down to 1.0 x 10(-9) A/cm(2) at -10 V in the 80%-silole-doped film. The 50%-silole-doped device showed high external quantum efficiency up to 60% along with the excellent color selectivity.
TAYLOR & FRANCIS LTD, English, Scientific journal
DOI：https://doi.org/10.1080/15421406.2012.710188DOI ID：10.1080/15421406.2012.710188,
ISSN：1542-1406,
Web of Science ID：WOS:000309285500012 Doping Effect of Ethylcarbazole-Contained-Silole in Blue-Sensitive Organic Photoconductive Device Sho Kimura; Takeshi Fukuda; Zentaro Honda; Norihiko Kamata; Keita Mori; Ken Hatano
MOLECULAR CRYSTALS AND LIQUID CRYSTALS,
Volume：566,
First page：54,
Last page：60, 2012,
[Reviewed]The photoconductive characteristics of the solution-processed organic device was improved by doping 1,1-dimethyl-2,5-bis(9-ethylcarbazol)-3,4-diphenylsilole(EtCz-silole) in poly(dioctylfluorenyl-co-benzo-thiadiazole) (F8BT). The maximum external quantum efficiency of 27% at - 38 MV/m was achieved when the doping concentration of EtCz-silole was 40 wt%. This value was approximately 160 times higher than that of the reference device with F8BT only (0.17%). In addition, the signal-to-noise ratio (S/N), i.e., photocurrent density/dark current density was improved by doping EtCz-silole due to the increased photocurrent density and the reduced dark current density. The highest S/N of 1.4 x 10(4) was observed by optimizing the concentration of EtCz-silole.
TAYLOR & FRANCIS LTD, English, Scientific journal
DOI：https://doi.org/10.1080/15421406.2012.701120DOI ID：10.1080/15421406.2012.701120,
ISSN：1542-1406,
eISSN：1563-5287,
Web of Science ID：WOS:000308766800010 Synthetic studies of bi-fluorescence-labeled maltooligosaccharides as substrates for alpha-amylase on the basis of fluorescence resonance energy transfer (FRET) Oka Hiroyuki; Koyama Tetsuo; Hatano Ken; Matsuoka Koji
Bioorganic & Medicinal Chemistry,
Volume：20,
Number：1,
First page：435,
Last page：445, 2012,
[Reviewed]DOI：https://doi.org/10.1016/j.bmc.2011.10.065DOI ID：10.1016/j.bmc.2011.10.065,
ORCID：41457008,
Web of Science ID：WOS:000298633300047 Synthesis and biological evaluation of sialic acid derivatives containing a long hydrophobic chain at the anomeric position and their C-5 linked polymers as potent influenza virus inhibitors Suzuki Kaori; Koyama Tetsuo; Yingsakmongkon Sangchai; Suzuki Yasuo; Hatano Ken; Matsuoka Koji
Bioorganic & Medicinal Chemistry,
Volume：20,
Number：1,
First page：446,
Last page：454, 2012,
[Reviewed]DOI：https://doi.org/10.1016/j.bmc.2011.10.064DOI ID：10.1016/j.bmc.2011.10.064,
ORCID：41457006,
Web of Science ID：WOS:000298633300048 その場で診断できる感染症検査薬をめざして(レーダー) 幡野 健; 松岡 浩司
Volume：59,
Number：11,
First page：560,
Last page：561, 2011
Japanese
DOI：https://doi.org/10.20665/kakyoshi.59.11_560DOI ID：10.20665/kakyoshi.59.11_560,
ISSN：0386-2151,
CiNii Articles ID：110008898224,
CiNii Books ID：AN10033386 Ultrafast study of charge generation in silole:fluorene mixed film for color selective organic photoconductive device Takeshi Fukuda; Ryohei Kobayashi; Zentaro Honda; Norihiko Kamata; Keita Mori; Yuu Suzuki; Ken Hatano; Akihiro Furube
PHYSICA STATUS SOLIDI C: CURRENT TOPICS IN SOLID STATE PHYSICS, VOL 8, NO 2,
Volume：8,
Number：2, 2011,
[Reviewed]Transient absorption characteristics of blue-sensitive organic thin films were investigated via a femtosecond pump-probe technique to estimate carrier kinetics. The most important finding is that the long-lived absorbance at 3440 nm increased with increasing the concentration of 1,1-dimethyl-2,5-bis(N, N-dimethylaminophenyl)-3,4-diphenylsilole (NMe2-silole). This fact indicates photoexcited carriers were dislocated in the organic layer, and the doping of NMe2-silole is considered to be useful method to improve photoconductive characteristics of organic devices.
[GRAPHICS]
Carrier kinetics model for NMe2-silole doped F8BT. (C) 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
WILEY-V C H VERLAG GMBH, English, International conference proceedings
DOI：https://doi.org/10.1002/pssc.201000454DOI ID：10.1002/pssc.201000454,
ISSN：1862-6351,
Web of Science ID：WOS:000301533800113 Synthesis of sialyllactosamine clusters using carbosilane as core scaffolds by means of chemical and enzymatic approaches Koji Matsuoka; Reina Kaneko; Tetsuo Koyama; XiaoTao Ma; Yasuaki Esumi; Takemichi Nakamura; Ken Hatano; Daiyo Terunuma
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS,
Volume：20,
Number：16,
First page：4906,
Last page：4910, Aug. 2010,
[Reviewed]An efficient synthesis of sialyllactosamine (SiaLacNAc) clusters using carbosilanes as core scaffolds has been accomplished by means of chemical and enzymatic approaches. N-Acetyl-D-glucosamine (GlcNAc) clusters having O-glycosidic linkage or S-glycosidic linkage were chemically synthesized from known intermediates in high yields. The GlcNAc clusters were first used as substrates for beta 1,4 galactosyl transferase using UDP-galactose (UDP-Gal) as a sugar source to provide corresponding N-acetyllactosamine clusters. Further sugar elongation of the LacNAc clusters was demonstrated using alpha 2,3 sialyl transferase and CMP-neuraminic acid (CMP-NANA) to yield the corresponding SiaLacNAc clusters. (c) 2010 Elsevier Ltd. All rights reserved.
PERGAMON-ELSEVIER SCIENCE LTD, English, Scientific journal
DOI：https://doi.org/10.1016/j.bmcl.2010.06.066DOI ID：10.1016/j.bmcl.2010.06.066,
ISSN：0960-894X,
ORCID：41457011,
Web of Science ID：WOS:000280348400038 Synthetic construction of a fucosyl chitobiose as an allergen-associated carbohydrate epitope and the glycopolymer involving highly clustered trisaccharidic sequences Koji Matsuoka; Hiroki Yamaguchi; Tetsuo Koyama; Ken Hatano; Daiyo Terunuma
TETRAHEDRON LETTERS,
Volume：51,
Number：18,
First page：2529,
Last page：2532, May 2010,
[Reviewed]Synthetic construction of fucosyl chitobiose [GlcNAc beta 1 -> 4(Fuc alpha 1 -> 3)GlcNAc] as an allergy-associated carbohydrate epitope was accomplished from three building blocks. The trisaccharidic unit was further transformed into a carbohydrate monomer and polymerization of the glycomonomer proceeded smoothly to provide a series of glycopolymers having various carbohydrate densities. In addition to the organic syntheses, biological evaluations of the glycomonomer and the polymers were carried out and sugar-clustering effects were observed. (C) 2010 Elsevier Ltd. All rights reserved.
PERGAMON-ELSEVIER SCIENCE LTD, English, Scientific journal
DOI：https://doi.org/10.1016/j.tetlet.2010.03.004DOI ID：10.1016/j.tetlet.2010.03.004,
ISSN：0040-4039,
ORCID：41457012,
Web of Science ID：WOS:000276972200039 Simple and conveniently accessible bi-fluorescence-labeled substrates for amylases Hiroyuki Oka; Tetsuo Koyama; Ken Hatano; Daiyo Terunuma; Koji Matsuoka
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS,
Volume：20,
Number：6,
First page：1969,
Last page：1971, Mar. 2010,
[Reviewed]Synthesis of bi-fluorescence-labeled maltooligosaccharides for amylase assay was accomplished. Preliminary biological evaluation of both bi-fluorescence-labeled maltohexasaccharide and maltose using alpha-amylase was carried out, and the hexaosyl derivative showed unique variation on the basis of fluorescence resonance energy transfer (FRET). (C) 2010 Elsevier Ltd. All rights reserved.
PERGAMON-ELSEVIER SCIENCE LTD, English, Scientific journal
DOI：https://doi.org/10.1016/j.bmcl.2010.01.117DOI ID：10.1016/j.bmcl.2010.01.117,
ISSN：0960-894X,
ORCID：41457010,
Web of Science ID：WOS:000275221500038 Analytical investigations of the behavior of silole-core dendrimers with peripheral globotriaose in water and acetone/water mixed solvent Hiroaki Aizawa; Ken Hatano; Hitoshi Saeki; Nobuaki Honsho; Tetsuo Koyama; Koji Matsuoka; Daiyo Terunuma
TETRAHEDRON LETTERS,
Volume：51,
Number：12,
First page：1545,
Last page：1549, Mar. 2010,
[Reviewed]A new compound having a 2,3,4,5-tetraphenylsilole derivative on the center silicon of Dumbbell(1)6Gb3; Silole-Dumbbell(1)6Gb3 (1) was previously reported. It was found that 1 exhibited strongly increased fluorescence both in water and in a 96% acetone/water mixed solvent. The physical behavior of 1 in water and in the 96% acetone/water mixed solvent was investigated, and analyses including fluorescence quantum yields, dynamic-light-scattering (DLS), atomic-force-microscopy (AFM), and fluorescence microscopy were carried Out. It was clarified that I dynamically formed different types of aggregates in water and in higher acetone concentrations to yield high aggregation-induced emission (AIE) effects due to the formation of micelle-like particles in water and inversion-type micelles in the acetone/water mixed solvent, respectively. Crown Copyright (C) 2010 Published by Elsevier Ltd. All rights reserved.
PERGAMON-ELSEVIER SCIENCE LTD, English, Scientific journal
DOI：https://doi.org/10.1016/j.tetlet.2010.01.041DOI ID：10.1016/j.tetlet.2010.01.041,
ISSN：0040-4039,
ORCID：41457009,
Web of Science ID：WOS:000275552000004 Improved Photoconductive Characteristics of Solution-Processed Organic Device by Doping Silole Derivative Ryohei Kobayashi; Takeshi Fukuda; Yuu Suzuki; Ken Hatano; Norihiko Kamata; Satoshi Aihara; Hokuto Seo; Daiyo Terunuma
MOLECULAR CRYSTALS AND LIQUID CRYSTALS,
Volume：519,
First page：206,
Last page：212, 2010,
[Reviewed]By doping 1,1-dimethyl-2,5-bis(N, N-dimethylaminophenyl)-3,4-diphenylsilole (silole-A) in poly(9,9-dioctylfluorene-alt-benzothiadiazole) (F8BT), an improved photoconductive characteristics was observed for a single layer organic device fabricated by a spin-coating process. A maximum external quantum efficiency (EQE) was 8.9% at -20 MV/m when the ratio of silole-A: F8BT was 75 mol%. The EQE of the reference device with F8BT only was 0.06%, and the highest EQE was approximately 160 times higher than that of the reference device. In addition, the photoluminescence (PL) quantum efficiency of the silole-A: F8BT neat film was lower than those of silole-A and F8BT neat films. The lower PL quantum efficiency indicates that the photo-induced carriers efficiently dislocate in the organic layer, resulting in the high EQE of organic photoconductive device.
TAYLOR & FRANCIS LTD, English, Scientific journal
DOI：https://doi.org/10.1080/15421401003594719DOI ID：10.1080/15421401003594719,
ISSN：1542-1406,
Web of Science ID：WOS:000277664700030 Relapsing fever Borrelia binds to neolacto glycans and mediates rosetting of human erythrocytes Betty P. Guo; Susann Teneberg; Robert Munch; Daiyo Terunuma; Ken Hatano; Koji Matsuoka; Jonas Angstrom; Thomas Boren; Sven Bergstrom
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA,
Volume：106,
Number：46,
First page：19280,
Last page：19285, Nov. 2009,
[Reviewed]A hallmark of acute relapsing fever borreliosis is severe bacteremia. Some Borrelia species, such as B. duttonii and B. crocidurae, associate with erythrocytes and induce aggregation recognized as erythrocyte rosetting. Erythrocyte rosettes contribute to disease severity by increased tissue invasiveness (such as invasion of CNS and encephalitis), hemorrhaging, and reduced blood flow in affected microcapillaries. Here we report that relapsing fever Borrelia binds to neolacto (Gal beta 4GlcNAc beta 3Gal beta 4Glc beta 1)-carrying glycoconjugates that are present on human erythrocytes. This interaction is of low affinity but is compensated for by the multivalency of neo-lacto-oligosaccharides on the erythrocyte cell surface. Hence, the protein-carbohydrate interaction is dependent on multivalent neolacto-glycans to mediate binding.
NATL ACAD SCIENCES, English, Scientific journal
DOI：https://doi.org/10.1073/pnas.0905470106DOI ID：10.1073/pnas.0905470106,
ISSN：0027-8424,
ORCID：41457015,
Web of Science ID：WOS:000271907400013 Fluorescence quenching detection of peanut agglutinin based on photoluminescent silole-core carbosilane dendrimer peripherally functionalized with lactose Ken Hatano; Hitoshi Saeki; Hiroo Yokota; Hiroaki Aizawa; Tetsuo Koyama; Koji Matsuoka; Daiyo Terunuma
TETRAHEDRON LETTERS,
Volume：50,
Number：42,
First page：5816,
Last page：5819, Oct. 2009,
[Reviewed]A glycocluster peripherally functionalized with a lactose (Lac: Gal beta 1 -> 4Glc beta 1-) derivative possessing a silole moiety as a luminophore was synthesized. The photoluminescence spectrum of the glycocluster showed extremely strong emission at 474 nm and the absolute quantum yield was estimated to be 92% in distilled water. The emission intensity was decreased by increasing the amount of peanut agglutinin (PNA), a lactose-binding lectin, and plots of the relative fluorescence intensity revealed a decline of 95% in emission intensity. Fluorescence quenching of the glycocluster upon mixing with PNA could be easily observed by the naked eye under UV irradiation, whereas no distinct change in fluorescence properties of the glycocluster was observed when wheat germ agglutinin (WGA) was employed. (C) 2009 Elsevier Ltd. All rights reserved.
PERGAMON-ELSEVIER SCIENCE LTD, English, Scientific journal
DOI：https://doi.org/10.1016/j.tetlet.2009.07.153DOI ID：10.1016/j.tetlet.2009.07.153,
ISSN：0040-4039,
ORCID：41457014,
Web of Science ID：WOS:000269967500013 Synthesis of sialic acid derivatives having a C = C double bond substituted at the C-5 position and their glycopolymers Kaori Suzuki; Jun-Ichi Sakamoto; Tetsuo Koyama; Sangchai Yingsakmongkon; Yasuo Suzuki; Ken Hatano; Daiyo Terunuma; Koji Matsuoka
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS,
Volume：19,
Number：17,
First page：5105,
Last page：5108, Sep. 2009,
[Reviewed]Glycomonomers of sialic acid in which the acetamide group at C-5 was converted into two kinds of C = C double bond substituents were prepared and the fully protected glycomonomers were directly polymerized before deprotection steps. Radical polymerization with acrylamide in DMF in the presence of ammonium persulfate and N,N,N',N'-tetramethylethylenediamine proceeded smoothly and gave corresponding sialopolymers. Interestingly glycomonomers had hemagglutination inhibitory activities not only for H1N1 but also for H3N2 of human influenza virus strains. (C) 2009 Elsevier Ltd. All rights reserved.
PERGAMON-ELSEVIER SCIENCE LTD, English, Scientific journal
DOI：https://doi.org/10.1016/j.bmcl.2009.07.034DOI ID：10.1016/j.bmcl.2009.07.034,
ISSN：0960-894X,
ORCID：41457018,
Web of Science ID：WOS:000268863800048 Syntheses and biological evaluations of carbosilane dendrimers uniformly functionalized with sialyl alpha(2 -> 3) lactose moieties as inhibitors for human influenza viruses Hiroyuki Oka; Tomotsune Onaga; Tetsuo Koyama; Chao-Tan Guo; Yasuo Suzuki; Yasuaki Esumi; Ken Hatano; Daiyo Terunuma; Koji Matsuoka
BIOORGANIC & MEDICINAL CHEMISTRY,
Volume：17,
Number：15,
First page：5465,
Last page：5475, Aug. 2009,
[Reviewed]A series of carbosilane dendrimers uniformly functionalized with sialyl lactose moieties (Neu5Ac alpha 2 -> 3-Gal beta 1 -> 4Glc) was systematically synthesized, and biological evaluations for anti-influenza virus activity using the glycodendrimers were performed. The results suggested that the glycodendrimers had unique biological activities depending on the form of their core frame, and Dumbbell(1)6-amide type glycoden-drimer 7 showed particularly strong inhibitory activities against human influenza viruses [A/PR/8/34 (H1N1) and A/Aichi/2/68 (H3N2)]. The results suggested that the structure-activity relationship (SAR) on the glycolibrary against various influenza viruses was observed, and dumbbell-shaped dendrimers as supporting carbohydrate moieties were found to be the most suitable core scaffolds in this study. (C) 2009 Elsevier Ltd. All rights reserved.
PERGAMON-ELSEVIER SCIENCE LTD, English, Scientific journal
DOI：https://doi.org/10.1016/j.bmc.2009.06.035DOI ID：10.1016/j.bmc.2009.06.035,
ISSN：0968-0896,
ORCID：41457016,
Web of Science ID：WOS:000268099700013 Highly luminescent glycocluster: silole-core carbosilane dendrimer having peripheral globotriaose Hatano Ken; Aizawa Hiroaki; Yokota Hiroo; Yamada Akihiro; Esumi Yasuaki; Koshino Hiroyuki; Koyama Tetsuo; Matsuoka Koji; Terunuma Daiyo
Tetrahedron Letters,
Volume：48,
Number：25,
First page：4365,
Last page：4368, 2007,
[Reviewed]DOI：https://doi.org/10.1016/j.tetlet.2007.04.100DOI ID：10.1016/j.tetlet.2007.04.100,
ORCID：40436946,
Web of Science ID：WOS:000247278100012 A highly-luminescent glycocluster in water: Silole-core carbosilane dendrimer having peripheral globotriaose
Ken Hatano; Hiroaki Aizawa; Hiroo Yokota; Koji Matsuoka; Daiyo Terunuma
Polymer Preprints, Japan, Volume：55, Number：2, First page：3007, Last page：3008, 2006
A novel glycocluster periphery functionalized by globotriaose (galα1-4Galβ1-4Glcβ1-) possessing a silole moiety as a luminophor was synthesized. The photoluminescence spectrum of the glycocluster in pure water showed extremely strong emission at 475 nm compared with that of other hydrophobic silole dendrimers.
Japanese, International conference proceedings
SCOPUS ID：33846133700
Synthetic studies of high-density-type glycopolymers (2)
Tetsuo Koyama; Ken Hatano; Daiyo Terunuma; Koji Matsuoka
Polymer Preprints, Japan, Volume：55, Number：1, First page：2088, 2006
Synthetic studies of functional molecules carrying lactose moieties have been investigated. These molecules were prepared from a glycosyl monomers, which have dimeric lactosyl residues, by radical polymerization and the glycopolymers have multivalent carbohydrate moieties as pendant-type epitopes. In order to investigate effective sugar-protein interactions induced by sugar-clustering effect, these glycopolymers were used as the synthetic receptors for lactose-specific lectins. The detail of the results and the synthesis of glycopolymers will be presented.
Japanese, International conference proceedings
SCOPUS ID：33749851551
Synthetic studies of novel water-soluble glycopolymers having sialic acid moieties (I)
Chiharu Takita; Jun-Ichi Sakamoto; Tetsuo Koyama; Ken Hatano; Daiyo Terunuma; Koji Matsuoka
Polymer Preprints, Japan, Volume：55, Number：1, First page：2087, 2006
Novel carbohydrate monomers having C=C double bond at ω position were synthesized from sialic acid as a starting material. Radical polymerization of the carbohydrate monomer and vinyl acetate in the presence of AIBN gave linear-type polymer bearing sialic acid moieties. The protections of the polymer were removed by using a combination of transesterification and saponification to give water-soluble glycopolymer in high yield.
Japanese, International conference proceedings
SCOPUS ID：33749823326
Identification and characterization of carbohydrate molecules in mammalian cells recognized by dengue virus type 2. Chie Aoki; Kazuya I.P.J. Hidari; Saki Itonori; Akihiro Yamada; Naonori Takahashi; Takeshi Kasama; Futoshi Hasebe; Mohammend Alimul Islam; Ken Hatano; Koji Matsuoka; Takao Taki; Chao-Tan Guo; Tadanobu Takahashi; Yuichi Sakano; Takashi Suzuki; Daisei Miyamoto; Mutsumi Sugita; Daiyo Terunuma; Koichi Morita; Yasuo Suzuki
J. Biochem.,
Volume：139,
First page：607,
Last page：614, 2006,
[Reviewed]English, Scientific journal
DOI：https://doi.org/10.1093/jb/mvj067DOI ID：10.1093/jb/mvj067 Syntheses and Vero toxin-binding activities of carbosilane dendrimers periphery-functionalized with galabiose Yamada Akihiro; Hatano Ken; Matsuoka Koji; Koyama Tetsuo; Esumi Yasuaki; Koshino Hiroyuki; Hino Kumiko; Nishikawa Kiyotaka; Natori Yasuhiro; Terunuma Daiyo
Tetrahedron,
Volume：62,
Number：21,
First page：5074,
Last page：5083, 2006,
[Reviewed]DOI：https://doi.org/10.1016/j.tet.2006.03.042DOI ID：10.1016/j.tet.2006.03.042,
ORCID：40436966,
Web of Science ID：WOS:000237485300006 Crystallization and preliminary X-ray analysis of the YjgF/YER057c/UK114-family protein ST0811 from Sulfolobus tokodaii strain 7.
Takuya Miyakawa; Ken Ichi Hatano; Woo Cheol Lee; Yusuke Kato; Yoriko Sawano; Fumiaki Yumoto; Koji Nagata; Masaru Tanokura
Acta crystallographica. Section F, Structural biology and crystallization communications, Volume：61, Number：Pt 9, First page：828, Last page：30, Sep. 2005, ［International magazine］
ST0811 from Sulfolobus tokodaii strain 7, a member of the YjgF/YER057c/UK114 protein family, was crystallized by the sitting-drop vapour-diffusion method using PEG 10,000 as precipitant. The crystals diffracted X-rays to beyond 2.0 A resolution using an in-house rotating-anode generator. The crystals belonged to the rhombohedral space group R3, with hexagonal unit-cell parameters a = b = 55.0, c = 223.2 A. The crystals contained two molecules in the asymmetric unit (VM = 2.3 A3 Da(-1)) and had a solvent content of 47%.
English, Scientific journal
eISSN：1744-3091, PubMed ID：16511170, PubMed Central ID：PMC1978107
Syntheses of carbosilane dendrimers carrying peripheral globotriaose derivatives - The relationship between the carbosilane dendrimer structure and the magnitude for neutralizing Shiga toxin-producing Escherichia coli O157 : H7D Terunuma; K Matsuoka; K Hatano
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN,
Volume：63,
Number：7,
First page：722,
Last page：727, Jul. 2005,
[Reviewed]As a novel type of artificial multivalent receptor for verotoxins, eight pairs of carbosilane dendrimers carrying up to 36 units of trisaccharide moieties of globotriaosyl ceramide (Gal alpha 1-4 Gal beta 1-4 Glc beta 1-Cer) were prepared. The receptors (referred to as SUPER TWIG) were obtained in a generally applicable one-pot reaction by treating periphery functionalized carbosilane dendrimers with globotriaose derivative which has a thiobenzyl ether moiety as a precursor for generation of thiolate anion under Birch reduction conditions. Biological estimations of SUPER TWIGs for inhibition of Shiga toxin-producing Escherichia coli O157: H 7 showed unexpected magnitude depend on the structure of the carbosilane dendrimer used both in vitro and in vivo. It was found that the carbosilane dendrimer carrying six periphery units of trisaccharide moieties (referred to as Dumbbell (1) 6) is one of the most effective agent among the SUPER TWIGs we prepared so far.
SOC SYNTHETIC ORGANIC CHEM JPN, Japanese, Scientific journal
ISSN：0037-9980,
ORCID：41457049,
Web of Science ID：WOS:000230525000005 Synthetic studies of high-density-type glycopolymers.-Driving for developing effecient Vero-toxin neutlizer
Tetsuo Koyama; Yusuke Goshu; Ken Hatano; Daiyo Terunuma; Koji Matsuoka
Polymer Preprints, Japan, Volume：54, Number：1, First page：2173, 2005
Synthetic studies of functional molecules carrying trisaccharide moieties of globotriaosyl ceramide (Gb3) have been investigated. These molecules displayed multivalent carbohydrate moieties on the surface and showed effective neutralizing activities against verotoxins produces by enteropathogenic Escherichia coli O157:H7. We will describe synthesis of novel glycopolymers having high density-type sugar moieties.
Japanese, International conference proceedings
SCOPUS ID：33645651591
Synthetic studies of carbosilane dendrimers functionalized with sugar moieties (IX) - Skelton effect on biological assay of lacto-n-neotetraose culsters as dengue virus inhibitory
Akihiro Yamada; Ken Hatano; Koji Matsuoka; Yasuaki Esumi; Chie Aoki; Kazuya Hidari; Yasuo Suzuki; Daiyo Terunuma
Polymer Preprints, Japan, Volume：54, Number：1, First page：2127, 2005
We have recently found that paragloboside and lacto-N-neotetraose blocked the uptake of dengue virus. We reported synthesis of carbosilane dendrimers periphery functionalized lacto-N-neotetraose. These glycoclusters obtained revealed adherence inhibition effect against dengue virus. The detailed results of biological assay will be discussed in this paper.
Japanese, International conference proceedings
SCOPUS ID：33645645777
Synthetic studies of sugar - Amino acid hybrid polymers(1)
Yusuke Goshu; Tetsuo Koyama; Ken Hatano; Daiyo Terunuma; Koji Matsuoka
Polymer Preprints, Japan, Volume：54, Number：1, First page：2174, 2005
Recently, we have found that synthetic receptors having globotriaosyl moieties completely neutralized the lethal dose of verotoxin produced by pathogenic E. coli O157:H7. In the course of our research, we are focusing relationship between structures and biological activities using synthetic glycopolymers. In this paper, we will report the preparation of novel globotriaose - amino acid hybrid polymers. Since the polymers have chiral amino acid near the polymer back bone, the polymers have a potential to display spiral form.
Japanese, International conference proceedings
SCOPUS ID：33645634507
Synthesis and characterization of new soluble Polydiphenylsilane derivatives
Toshiyuki Sato; Ken Hatano; Norihiko Kamata; Koji Matsuoka; Daiyo Terunuma
Polymer Preprints, Japan, Volume：54, Number：1, First page：337, 2005
Four types of copolymer(3a, 3b, 3c, 3d) were newly synthesized by polycondensation of α, ω -dilithiopolysilane derived from decaphenylcyclopentasilane(2) with dichlorosilanes(3a, 3b, 3c) and dichlorodisilane(3d). The reaction of 2 with dichlorosilanes(3a, 3b, 3c) gave the corresponding polymers. But main-products were five- and six-membered cyclic oligosilanes due to intramolecular-cyclization of the intermediates. On the other hand, with dichlorodisilane(3d), the amount of liner polysilane increased because the seven-memberd cyclic oligosilane is more difficult to form than the five- or six-membered cyclic oligosilanes.
Japanese, International conference proceedings
SCOPUS ID：33645575319
Syntheses of new polysilanes bearing pendant liquid-crystalline molecules (II)
Hideki Takahashi; Ken Hatano; Yoshio Aoki; Koji Matsuoka; Norihiko Kamata; Daiyo Terunuma
Polymer Preprints, Japan, Volume：54, Number：1, First page：443, 2005
Polysilanes with pendant liquid-crystalline molecules, which consist of a methylene spacer and cyclohexylphenyl moiety as a mesogen core, were synthesized. The polysilanes were quite soluble in organic solvents such as THF and chloroform. The polysilanes were characterized by IR, UV-vis, PL, and 1H-NMR. Phase transition of the obtained polymer a was indicative of Tg (= 122°C) and Tc (=132°C) by polarized optical microscope. While, phase transition of the obtained polymer b was not indicative of clear Tg and Tc.
Japanese, International conference proceedings
SCOPUS ID：33645572418
Syntheses and structures of silicon analogues of cyclopropabenzenes Tomoyuki Tajima; Ken Hatano; Takayo Sasaki; Takahiro Sasamori; Nobuhiro Takeda; Norihiro Tokitoh; Nozomi Takagi; Shigeru Nagase
Journal of Organometallic Chemistry,
Volume：686,
Number：1-2,
First page：118,
Last page：126, Dec. 2003
The reactions of an overcrowded diaryldilithiosilane, Tbt(Dip)SiLi 2 (Tbt=2,4,6-tris[bis(trimethylsilyl)methyl]phenyl; Dip=2,6-diisopropylphenyl), with o-dibromobenzene and 1,2,4, 5-tetrabromobenzene resulted in the synthesis and isolation of the first stable silacyclopropabenzene and bis(silacyclopropa)benzenes (IUPAC name is 4,8-disilatricyclo[5.1.0.03,5]octa-1,3(5), 6-triene), respectively. The crystallographic analyses and theoretical calculations revealed that the lengths of the juncture carbon-carbon bonds of the mono- and bis(silacyclopropa)benzenes were marginally in the range of carbon-carbon bond lengths of usual benzene rings. It is shown that this structural feature is attributable to a decrease in the strain energy of silacyclopropabenzenes relative to the corresponding cyclopropabenzenes, and the strain energy is a simple additive function of the number of the fused three-membered rings involving Si atom. © 2003 Elsevier B.V. All rights reserved.
Scientific journal
DOI：https://doi.org/10.1016/S0022-328X(03)00446-7Scopus：https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=0142025005&origin=inwardScopus Citedby：https://www.scopus.com/inward/citedby.uri?partnerID=HzOxMe3b&scp=0142025005&origin=inwardDOI ID：10.1016/S0022-328X(03)00446-7,
ISSN：0022-328X,
SCOPUS ID：0142025005 The First Examples of Stable Benzenes Fused with Two Three-membered Rings : Synthesis and Structures of the Two Stereoisomers of Bis(silacyclopropa)benzenes TAJIMA Tomoyuki; HATANO Ken; SASAKI Takayo; SASAMORI Takahiro; TAKEDA Nobuhiro; TOKITOH Norihiro
Chemistry Letters,
Volume：32,
Number：3,
First page：220,
Last page：221, Mar. 2003
Two stereoisomers of the first stable bis(silacyclopropa)benzenes (
1a,
1b) were successfully synthesized by the reaction of Tbt(Dip)SiLi
2 (
3) [Tbt = 2,4,6-tris[bis(trimethylsilyl)methyl]phenyl, Dip = 2,6-diisopropylphenyl] with 1,2,4,5-tetrabromobenzene. The molecular structures of
1a and
1b were discussed on the basis of the X-ray structural analyses.
The Chemical Society of Japan, English
DOI：https://doi.org/10.1246/cl.2003.220DOI ID：10.1246/cl.2003.220,
ISSN：0366-7022,
CiNii Articles ID：10012814431,
CiNii Books ID：AA00603318 Preparation of new carbosilane dendrimers having terminal mesogens and investigation of their liquid crystal characteristicsT Tsuchida; C Shimazaki; K Hatano; K Matsuoka; Y Aoki; H Nohira; Y Esumi; D Terunuma
KOBUNSHI RONBUNSHU,
Volume：60,
Number：10,
First page：561,
Last page：568, 2003,
[Reviewed]Both of a series of new second generation carbosilane dendrimers having a different number of branches (Me(n)G 2-Mesogen, n=1, 2, 3) and a novel carbosilane dendrimer having an increased length of methylene chain from the core to the second generation (Gradient G 2-Mesogen) with terminal cyanobiphenyl mesogens were prepared. The characterization of the dendrimers was carried out by using differential scanning calorimetry (DSC) and optical polarizing microscopy. All the dendrimers showed smectic A phase. The ranges of the smectic A phase and the texture size of Me(n)G 2-Mesogen were increased with increasing the number of branches. The behavior of phase transition temperature and the texture size of Gradient G 2-Mesogen were similar to those of Me(n)G-2 Mesogen.
SOC POLYMER SCIENCE JAPAN, Japanese, Scientific journal
ISSN：0386-2186,
ORCID：41457057,
Web of Science ID：WOS:000186308000006 Synthesis and isolation of the first germacyclopropabenzene: A study to elucidate the intrinsic factor for the ring deformation of cyclopropabenzene skeletons Norihiro Tokitoh; Ken Hatano; Takayo Sasaki; Takahiro Sasamori; Nobuhiro Takeda; Nozomi Takagi; Shigeru Nagase
Organometallics,
Volume：21,
Number：21,
First page：4309,
Last page：4311, Oct. 2002
A study was performed to elucidate the intrinsic factor for the ring deformation of cyclopropabenzene skeletons. The treatment of an overcrowded diaryldilithiogermane, Tbt(Dip)GeLi2 (Tbt = 2,4,6,-tris[bis(trim-ethylsilyl)methyl]phenyl; Dip = 2,6-diisopropylphenyl), generated by exhaustive reduction of the corresponding dibromogermane Tbt(Dip)GeBr2, with 1,2-dibromobenzene resulted in the isolation of the germacyclopropabenzene. The experimental results were in good agreement with those obtained by theoretical calculations.
Scientific journal
DOI：https://doi.org/10.1021/om020545xScopus：https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=0037561122&origin=inwardScopus Citedby：https://www.scopus.com/inward/citedby.uri?partnerID=HzOxMe3b&scp=0037561122&origin=inwardDOI ID：10.1021/om020545x,
ISSN：0276-7333,
SCOPUS ID：0037561122 Generation and Reactions of an Overcrowded Diaryldilithiosilane TOKITOH Norihiro; HATANO Ken; SADAHIRO Tomoyuki; OKAZAKI Renji
Chemistry Letters,
Volume：1999,
Number：9,
First page：931,
Last page：932, Sep. 1999
Exhaustive reduction of dibromo(2,6-diisopropylphenyl){2,4,6-tris[bis(trimethylsilyl)methyl]phenyl}silane with excess amount of lithium naphthalenide (more than 4 molar amounts) in tetrahydrofuran at −78 °C gave the corresponding dilithiosilane, the effective formation of which was confirmed by the trapping experiments with a variety of electrophiles. The diaryldilithiosilane thus generated was found to be stable at −78 °C but undergo an intramolecular proton abstraction to give the lithium-migrated dilithiosilane.
1The Chemical Society of Japan, English
DOI：https://doi.org/10.1246/cl.1999.931DOI ID：10.1246/cl.1999.931,
ISSN：0366-7022,
CiNii Articles ID：10005718412,
CiNii Books ID：AA00603318
Carbosilane glycodendrimers Ken Hatano; Koji Matsuoka; Daiyo Terunuma
Chemical Society Reviews,
Volume：42,
Number：11,
First page：4574,
Last page：4598, 07 Jun. 2013
Glycodendrimers fascinate both carbohydrate chemists and biologists because of their ability to recognize lectins and enhance carbohydrate-protein interactions. These characteristics make glycodendrimers a valuable tool in glycoscience and chemical biology. Many glycodendrimers have been described to date
this tutorial review focuses specifically on carbosilane glycodendrimers. We present methodologies for synthesizing parent carbosilane dendrimers and describe their use in biological assays. We also describe representative functionalizations of parent carbosilane dendrimers at terminal positions which are necessary for chemical ligation with carbohydrate ligands. This is followed by a description of all coupling reactions between carbohydrate and carbosilane dendrimer functionalities used in the synthesis of carbosilane glycodendrimers. The major emphasis of this review is the use of carbosilane glycodendrimers as medical agents against Shiga toxins, dengue viruses, relapsing fever Borrelia, and hemagglutinin and neuraminidase of influenza viruses, as well as on the relationship between dendrimer structure and these biological activities. The last two sections introduce recent attempts to use carbosilane glycodendrimers as new versatile and widely-applicable lectin sensors, and the use of carbosilane glycodendrimers as a novel drug carrier in an active targeting drug delivery system. This review article will be of interest to scientists in the areas of organic chemistry, chemical biology, carbohydrate chemistry, heteroatom chemistry, and organosilicon chemistry. © 2013 The Royal Society of Chemistry.
English, Book review
DOI：https://doi.org/10.1039/c2cs35421gDOI ID：10.1039/c2cs35421g,
ISSN：0306-0012,
PubMed ID：23257960,
SCOPUS ID：84877819735 Glyco-silicon functional materials as anti-influenza virus agents Koji Matsuoka; Tetsuo Koyama; Ken Hatano
Open Glycoscience,
Volume：5,
Number：1,
First page：31,
Last page：40, 2012
This review shows introduction of glycoclusters using carbosilanes as core scaffolds, preparations of glyco-clusters and their excellent properties as well as functions. Since a dendrimer has unique advantages such as single mo-lecular weight, regularity of structure and easy control of shape and size, dendrimers are utilized in various research areas. Results of syntheses and biological evaluations of the carbosilane dendrimers having carbohydrate moieties for influenza viruses are presented. © Matsouka et al.
English, Book review
DOI：https://doi.org/10.2174/1875398101205010031DOI ID：10.2174/1875398101205010031,
ISSN：1875-3981,
SCOPUS ID：84861876640 Development of multitasking biosensor for bacteria and viruses based on glyco-cluster effect
幡野 健; 松岡 浩司
Bio industry, Volume：28, Number：3, First page：55, Last page：59, Mar. 2011
Japanese
ISSN：0910-6545, CiNii Articles ID：40018715008, CiNii Books ID：AN10039203
Novel synthetic method to attach functional sugar chains on gold-nanoparticles小山 哲夫; 幡野 健; 松岡 浩司
Volume：3,
First page：49,
Last page：49, 2011
Multivalent structure with carbohydrate moieties and its biological properties have been studied. Novel method for synthesizing gold-nano-particles carrying carbohydrate moieties have been developed and the method is much more convenient than a traditional method. Expection of the glyco-gold-nanoparticle is display of multivalent carbohydrate moieties on the surface and show of effective interaction with pathogens. In addition it has capability of applying to diagnostric use such as medical test kit.
Japanese
CiNii Articles ID：120003088323 Improvements in photoconductive characteristics of organic device using silole derivative Takeshi Fukuda; Ryohei Kobayashi; Norihiko Kamata; Satoshi Aihara; Hokuto Seo; Ken Hatano; Daiyo Terunuma
Japanese Journal of Applied Physics,
Volume：49,
Number：1,
First page：01AC05-1-01AC05-4, 2010
Poly[9,9-dioctylfluorenyl-2,7-diyl]-co-1,4-benzo-(2, 1, 3)-thiadiazole (F8BT) is one of the suitable materials for color-selective organic photoconductive devices owing to its high carrier mobility and absorption coefficient against only the blue light. We investigated a mixing method using a silole derivative, 1,1 -dimethyl-2,3,4,5-tetraphenylsilole (DMTPS), in F8BT to improve the ratio between photocurrent and dark current (ON/OFF ratio), which is an important parameter for practical organic photoconductive devices. These organic materials can be coated by a solution process, which leads us to realize a low fabrication cost and a large device area in the future. By adding DMTPS into F8BT, the maximum improvement in ON/OFF ratio of 5 times was achieved compared with the reference device with F8BT only
however, the external quantum efficiency was independent of the concentration of DMTPS less than 50 wt%. In addition, the wavelength selectivity of DMTPS:F8BT in the visible wavelength region was almost the same as that of F8BT only. This result indicates that the DMTPS:F8BT layer can absorb only the blue light, indicating the possibility of a color separation without a prism for high-resolution cameras by combining the green- and red-sensitive devices. © 2010 The Japan Society of Applied Physics.
English
DOI：https://doi.org/10.1143/JJAP.49.01AC05DOI ID：10.1143/JJAP.49.01AC05,
ISSN：0021-4922,
SCOPUS ID：77950801842 Improvements in Photoconductive Characteristics of Organic Device Using Silole Derivative Takeshi Fukuda; Ryohei Kobayashi; Norihiko Kamata; Satoshi Aihara; Hokuto Seo; Ken Hatano; Daiyo Terunuma
JAPANESE JOURNAL OF APPLIED PHYSICS,
Volume：49,
Number：1,
First page：01AC05-1-01AC05-4, 2010
Poly[9,9-dioctylfluorenyl-2,7-diyl]-co-1,4-benzo-(2,1,3)-thiadiazole (F8BT) is one of the suitable materials for color-selective organic photoconductive devices owing to its high carrier mobility and absorption coefficient against only the blue light. We investigated a mixing method using a silole derivative, 1,1-dimethyl-2,3,4,5-tetraphenylsilole (DMTPS), in F8BT to improve the ratio between photocurrent and dark current (ON/OFF ratio), which is an important parameter for practical organic photoconductive devices. These organic materials can be coated by a solution process, which leads us to realize a low fabrication cost and a large device area in the future. By adding DMTPS into F8BT, the maximum improvement in ON/OFF ratio of 5 times was achieved compared with the reference device with F8BT only; however, the external quantum efficiency was independent of the concentration of DMTPS less than 50wt %. In addition, the wavelength selectivity of DMTPS:F8BT in the visible wavelength region was almost the same as that of F8BT only. This result indicates that the DMTPS:F8BT layer can absorb only the blue light, indicating the possibility of a color separation without a prism for high-resolution cameras by combining the green- and red-sensitive devices. (C) 2010 The Japan Society of Applied Physics
JAPAN SOC APPLIED PHYSICS, English
DOI：https://doi.org/10.1143/JJAP.49.01AC05DOI ID：10.1143/JJAP.49.01AC05,
ISSN：0021-4922,
Web of Science ID：WOS:000279288900021 Synthesis and Characterization of Photo-Responsive Carbosilane Dendrimers Tetsuo Koyama; Ken Hatano; Koji Matsuoka; Yasuaki Esumi; Daiyo Terunuma
MOLECULES,
Volume：14,
Number：6,
First page：2226,
Last page：2234, Jun. 2009
Preparation of photo-responsive carbosilane dendrimers bearing 4-phenylazobenzonitrile units on their molecular surface has been accomplished, and their both photo and thermal behaviors have also been characterized. These functional dendrimers suggest that the apparent molecular sizes of the cis-isomers are smaller than those of the corresponding trans-isomers, since the molecular diameter of these dendrimers would be shorter on the basis of trans -> cis photo-isomerization of azobenzene.
MOLECULAR DIVERSITY PRESERVATION INTERNATIONAL-MDPI, English
DOI：https://doi.org/10.3390/molecules14062226DOI ID：10.3390/molecules14062226,
ISSN：1420-3049,
Web of Science ID：WOS:000267339500024 Color-selective organic photoconductive device fabricated by wet process
福田 武司; 小林 諒平; 幡野 健; 鎌田 憲彦; 照沼 大陽
Number：2, First page：56, Last page：60, 2009
Organic image sensor have been attracting considerable attention for sensing applications owing toseveral special characteristics compared to semiconductor materials, such as high absorption coefficient, flexibility, stacked structure, and low fabrication cost. By now, our research group reported a color selective organic photoconductive device via a wet process. In this report, we investigated optical characteristics of a blue-sensitive organic photoconductive device by doping several silole derivatives to improve a device performance. We used poly(dioctylfluorenyl-co-benzo-thiadiazole) [F8BT] as a photoconductive and bluesensitive polymer because of its high carrier mobility and absorption coefficient. Most of silole derivativesshowed only the absorption bands at blue or violet wavelength regions. Therefore, silole derivative is found to be suitable material for a blue-sensitive organic photoconductive device. A maximum external quantum efficiency of 8.9% was obtained by doping 1,1-dimethyl-2,5-bis(N,N-dimethylaminophenyl)-3,4-diphenylsilole in F8BT. This value was two orders higher than that of the reference device with F8BT only.
Japanese
ISSN：1883-8278, CiNii Articles ID：120002354120, CiNii Books ID：AA12486867
Systematic syntheses of influenza neuraminidase inhibitors: A series of carbosilane dendrimers uniformly functionalized with thioglycoside-type sialic acid moieties. Jun-Ichi Sakamoto; Tetsuo Koyama; Daisei Miyamoto; Sangchai Yingsakmongkon; Kazuya I.P.J. Hidari; Wipawee Jampangern; Takashi Suzuki; Yasuo Suzuki; Yasuaki Esumi; Takemichi Nakamura; Ken Hatano; Daiyo Terunuma; Koji Matsuoka
Bioorg. Med. Chem.,
Volume：17,
First page：5451,
Last page：5464, 2009
DOI：https://doi.org/10.1016/j.bmc.2009.06.036DOI ID：10.1016/j.bmc.2009.06.036 Synthetic construction of a Le(x) determinant via gabriel amine synthesis and the glycopolymer involving highly clustered Le(x) residues K. Matsuoka; T. Kohzu; T. Hakumura; T. Koyama; K. Hatano; D. Terunuma
Tetrahedron Letters,
Volume：50,
Number：21,
First page：2593,
Last page：2596, 2009
DOI：https://doi.org/10.1016/j.tetlet.2009.03.099DOI ID：10.1016/j.tetlet.2009.03.099,
ISSN：0040-4039,
CiNii Articles ID：80020274265 Use of a recycle-type SEC method as a powerful tool for purification of thiosialoside derivatives Jun-Ichi Sakamoto; Chiharu Takita; Tetsuo Koyama; Ken Hatano; Daiyo Terunuma; Koji Matsuoka
CARBOHYDRATE RESEARCH,
Volume：343,
Number：16,
First page：2735,
Last page：2739, Nov. 2008
An efficient separation between fully acetylated thiosialoside methyl esters and fully acetylated Neu5A-c2en methyl esters was accomplished by means of a size-exclusion chromatography (SEC) method. Purity determinations and structural elucidation of the isolated compounds were performed by a combination of elemental analyses and spectroscopic analyses, including IR, (1)H, and (13)C NMR, and mass spectroscopic analyses. (C) 2008 Elsevier Ltd. All rights reserved.
ELSEVIER SCI LTD, English
DOI：https://doi.org/10.1016/j.carres.2008.05.014DOI ID：10.1016/j.carres.2008.05.014,
ISSN：0008-6215,
CiNii Articles ID：80019881611,
Web of Science ID：WOS:000260735900003 Synthesis and lectin-binding activity of luminescent silica particles peripherally functionalized with lactose Ken Hatano; Tetsuya Yamazaki; Koji Yoshino; Naoto Ohyama; Tetsuo Koyama; Koji Matsuoka; Daiyo Terunuma
TETRAHEDRON LETTERS,
Volume：49,
Number：39,
First page：5593,
Last page：5596, Sep. 2008
A novel O-protected lactose (Gal beta 1 -> 4Glc beta 1-) derivative bearing trimethoxysilyl group at the aglycon was developed as a silane coupling agent. Reaction of the coupling agent with tris(2,2'-bipyridine)ruthenium (II) dlichloride (Rubpy) doped silica particle gave a Rubpy-doped silica particle peripherally functionalized with O-protected lactose derivative. De-O-protection of the particle with aqueous ammonia provided lactose-coating Rubpy-doped silica particles, combining luminophor encapsulated in silica matrix and carbohydrate having lectin-recognition ability. Specific adhesion of fluorescein isothiocyanate-labeled peanut agglutinin (FITC-PNA) to the lactose-coating Rubpy-doped silica particles was confirmed by fluorescence microscopic analysis. (C) 2008 Elsevier Ltd. All rights reserved.
PERGAMON-ELSEVIER SCIENCE LTD, English
DOI：https://doi.org/10.1016/j.tetlet.2008.07.034DOI ID：10.1016/j.tetlet.2008.07.034,
ISSN：0040-4039,
CiNii Articles ID：80019747433,
Web of Science ID：WOS:000259309700008 Sialyl alpha(2 -> 3) lactose clusters using carbosilane dendrimer core scaffolds as influenza hemagglutinin blockers Hiroyuki Oka; Tomotsune Onaga; Tetsuo Koyama; Chao-Tan Guo; Yasuo Suzuki; Yasuaki Esumi; Ken Hatano; Daiyo Terunuma; Koji Matsuoka
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS,
Volume：18,
Number：15,
First page：4405,
Last page：4408, Aug. 2008
An efficient synthesis of a series of carbosilane dendrimers uniformly functionalized with sialyl alpha(2 -> 3) lactose (Neu5Ac alpha(2 -> 3)Gal beta(1 -> 4)Glc beta 1 ->) moieties was accomplished. The results of a preliminary study on biological responses against influenza virus hemagglutinin, using the sialyl lactose clusters showed unique biological activities on the basis of the structure-activity relationship according to the carbosilane scaffolds. (c) 2008 Elsevier Ltd. All rights reserved.
PERGAMON-ELSEVIER SCIENCE LTD, English
DOI：https://doi.org/10.1016/j.bmcl.2008.06.101DOI ID：10.1016/j.bmcl.2008.06.101,
ISSN：0960-894X,
PubMed ID：18639456,
Web of Science ID：WOS:000257986400034 Lectin detection based on photoluminescent silole-core carbosilane dendrimer peripherally functionalized with carbohydrate佐伯 整; 幡野 健; 横田 洋大; 相澤 宏明; 小山 哲夫; 松岡 浩司; 照沼 大陽
Volume：42,
First page：14,
Last page：18, 2008
A glycocluster periphery functionalized with lactose derivative possessing a silole moiety as a luminophore was synthesized. The photoluminescence spectrum of the glycocluster showed extremely strong emission at 475 nm and the absolute quantum yield was estimated to be 92% in water. The emission intensity was decreased by increasing the amount of peanut agglutinin (PNA), lactose-binding lectin, eventually to be nearly one-twentieth of the intensity in the case of absence of PNA. The fluorescence quenching of the glycocluster on mixing with PNA can be easily distinguished with the naked-eye observation under UV irradiation. Whereas no distinct change in the fluorescence properties of the glycoclyster was observed when wheat germ agglutinin (WGA) was employed.
Japanese
CiNii Articles ID：120005373728 標的認識能を有する有機ケイ素-糖鎖ハイブリッド材料
照沼大陽; 松岡浩司; 幡野健
未来材料, Volume：8, First page：45, Last page：50, 2008
糖鎖と有機ケイ素化合物の複合による新規機能材料
幡野健; 松岡浩司; 照沼大陽
化学工業, Volume：59, Number：2, First page：95, Last page：100, 2008
Thiosialoside Clusters Using Carbosilane Dendrimer Core Scaffolds as a New Class of Influenza Neuraminidase Inhibitors J.-I. Sakamoto; T. Koyama; D. Miyamoto; S. Yingsakmongkon; K.I.P.J. Hidari; W. Jampangern; T. Suzuki; Y. Suzuki; Y. Esumi; K. Hatano; D. Terunuma; K. Matsuoka
Bioorg. Med. Chem. Lett.,
Volume：17,
Number：3,
First page：717,
Last page：721, 2007
DOI：https://doi.org/10.1016/j.bmcl.2006.10.085DOI ID：10.1016/j.bmcl.2006.10.085,
ISSN：0960-894X,
PubMed ID：17095224 Practical Synthesis of Fully Protected Globotriaose and Its Glycopolymers K. Matsuoka; Y. Goshu; Y. Takezawa; T. Mori; J.-I. Sakamoto; A. Yamada; T. Onaga; T. Koyama; K. Hatano; P. W. Snyder; E. J. Toone; D. Terunuma
Carbohydr. Polym.,
Volume：69,
Number：2,
First page：326,
Last page：335, 2007
DOI：https://doi.org/10.1016/j.carbpol.2006.10.011DOI ID：10.1016/j.carbpol.2006.10.011,
ISSN：0144-8617,
CiNii Articles ID：80018527330 Novel Linear Polymers Bearing Thiosialosides as Pendant-type Epitopes for Influenza Neuraminidase Inhibitors K. Matsuoka; C. Takita; T. Koyama; D. Miyamoto; S. Yingsakmongkon; K. I.P.J. Hidari; W. Jampangern; T. Suzuki; Y. Suzuki; K. Hatano; D. Terunuma
Bioorg. Med. Chem. Lett.,
Volume：17,
Number：14,
First page：3826,
Last page：3830, 2007
DOI：https://doi.org/10.1016/j.bmcl.2007.05.016DOI ID：10.1016/j.bmcl.2007.05.016,
ISSN：0960-894X,
PubMed ID：17524642 Lactotriaose-containing carbosilane dendrimers: syntheses and lectin-binding activities A. Yamada; K. Hatano; T. Koyama; K. Matsuoka; N. Takahashi; K.I.P.J. Hidari; Y. Suzuki; D. Terunuma
Bioorg. Med. Chem.,
Volume：15,
Number：4,
First page：1606,
Last page：1614, 2007
DOI：https://doi.org/10.1016/j.bmc.2006.12.030DOI ID：10.1016/j.bmc.2006.12.030 患部の蛍光標識を目指した糖鎖ーケイ素ハイブリッド型材料の開発に関する基礎研究
幡野 健
Number：5(18年度), First page：543, Last page：544, 2007
患部の蛍光標識を目指した糖鎖ーケイ素ハイブリッド型材料の開発に関する基礎研究
幡野 健
総合研究機構研究プロジェクト研究成果報告書, Number：5(18年度), First page：543, Last page：544, 2007
Thiosialoside Clusters as Inhibitors for Influenza Virus Neuraminidases
J.-I. Sakamoto; C. Takita; T. Koyama; K. Hatano; D. Terunuma; Y. Esumi; K. I.-P; J. Hidari; S. Yingsakmongkon; D. Miyamoto; W. Usawattanakul; T. Suzuki; Y. Suzuki; K. Matsuoka
22nd International Symposium on the Organic Chemistry of Sulfur, First page：173, 2006
Synthetic Construction of Novel Sugar―Amino Acid Hybrid Materials Using Typical Radical Polymerization Protocol
K. Matsuoka; Y. Goshu; T. Koyama; K. Hatano; D. Terunuma
XXIIIrd International Carbohydrate Symposium, First page：275, 2006
Synthesis of a Series of Carbosilane Dendrimers Having Thioglycoside-type Sialic Acid Moieties
J.-I. Sakamoto; T. Koyama; Y. Esumi; H. Koshino; K. I.-P; J. Hidari; T. Suzuki; Y. Suzuki; K. Hatano; D. Terunuma; K. Matsuoka
XXIIIrd International Carbohydrate Symposium, First page：279, 2006
Syntheses of a Series of Lacto-N-neotetraose Clusters using a Carbosilane Dendrimer Scaffold A. Yamada; K. Hatano; T. Koyama; K. Matsuoka; Y. Esumi; Daiyo Terunuma
Carbohydr. Res.,
Volume：341,
Number：4,
First page：467,
Last page：473, 2006
DOI：https://doi.org/10.1016/j.carres.2005.11.037DOI ID：10.1016/j.carres.2005.11.037,
ISSN：0008-6215,
CiNii Articles ID：80019328422,
PubMed ID：16386236 Carbosilane Dendrimers Bearing Globotriaoses: Syntheses of Globotrioasyl Derivative and Introduction into Carbosilane Dendrimers K. Matsuoka; M. Terabatake; A. Umino; Y. Esumi; K. Hatano; D. Terunuma; H. Kuzuhara
Biomacromolecules,
Volume：7,
Number：8,
First page：2274,
Last page：2283, 2006
DOI：https://doi.org/10.1021/bm060368+DOI ID：10.1021/bm060368+,
ISSN：1525-7797,
CiNii Articles ID：80018973734,
PubMed ID：16903671 Carbosilane Dendrimers Bearing Globotriaoses: Construction of A Series of Carbosilane Dendrimers Bearing Globotriaoses K. Matsuoka; M. Terabatake; Y. Esumi; K. Hatano; D. Terunuma; H. Kuzuhara
Biomacromolecules,
Volume：7,
Number：8,
First page：2284,
Last page：2290, 2006
DOI：https://doi.org/10.1021/bm0603692DOI ID：10.1021/bm0603692,
ISSN：1525-7797,
CiNii Articles ID：80018973735,
PubMed ID：16903672 Identification of the Optimal Structure Required for a Shiga Toxin Neutralizer with Oriented Carbohydrates to Function in the Circulation K. Nishikawa; K. Matsuoka; M. Watanabe; K. Igai; K. Hino; K. Hatano; A. Yamada; N. Abe; D. Terunuma; H. Kuzuhara; Y. Natori
J. Infect. Dis.,
Volume：191,
Number：12,
First page：2097,
Last page：2105, 2005
DOI：https://doi.org/10.1086/430388DOI ID：10.1086/430388 グロボ三糖担持カルボシランデンドリマーの合成 -カルボシランデンドリマー構造がO157:H7が産生するベロ毒素の阻害活性に及ぼす効果- (Review) 照沼大陽; 松岡浩司; 幡野健
有機合成化学協会誌,
Volume：63,
Number：7,
First page：722,
Last page：727, 2005
DOI：https://doi.org/10.5059/yukigoseikyokaishi.63.722DOI ID：10.5059/yukigoseikyokaishi.63.722,
ISSN：0037-9980,
CiNii Articles ID：10016587901 Synthesis of Carbosilane Dendrimers Having Peripheral Mannose and Mannobiose T. Mori; K. Hatano; K. Matsuoka; Y. Esumi; E. J. Toone; D. Terunuma
Tetrahedron,
Volume：61,
Number：11,
First page：2751,
Last page：2760, 2005
DOI：https://doi.org/10.1016/j.tet.2005.01.090DOI ID：10.1016/j.tet.2005.01.090,
ISSN：0040-4020,
CiNii Articles ID：80017259179 Syntheses and Biological Assay of a Series of Lacto-N-neotetraose Cluster using Carbosilane Dendrimer Scaffolds
Akihiro, Yamada; Ken Hatano; Koji Matsuoka; Yasuaki Esumi; Chie Aoki; Kazuya Hidari; Yasuo Suzuki; Daiyo Terunuma
The 14th International Symposium on Organosilicon Chemistry, First page：134, 2005
Advantages of Carbosilane Dendrimer as a Carbohydrate Scaffold --Application to Artificial Receptor of E. Coli, Influenza and Dengue Virus--
Ken Hatano; Akihiro Yamada; Tetsuo Koyama; Koji Matsuoka; Daiyo Terunuma; Yasuaki Esumi; Kiyotaka Nishikawa; Yasuhiro Natori; Kazuya Hidari; Yasuo Suzuki
The 14th International Symposium on Organosilicon Chemistry, First page：78, 2005
カルボシランデンドリマー・糖鎖複合材料の開発 : 大腸菌O157の産生するベロ毒素中和剤への応用<論文>
幡野 健; 松岡 浩司; 照沼 大陽
Volume：1, Number：38, First page：40, Last page：44, 2005
カルボシランデンドリマー・糖鎖複合材料の開発 : 大腸菌O157の産生するベロ毒素中和剤への応用<論文>幡野 健; 松岡 浩司; 照沼 大陽
埼玉大学紀要, 工学部, 第1部論文集,
Volume：1,
Number：38,
First page：40,
Last page：44, 2005
Carbosilane dendrimer periphery bearing globotiaose were synthesized by SN2 reaction of thiolate anion at aglycon of globotriaose and brominated carbosilane dendrimer. Binding assay of tree shapes of carbosilane dendrimers [Fan(0)3, Dumbbell(1)6 and Ball(1)12] were carried out. Vero toxin classified into two closely related subgroups, Stx1 and Stx2. Dumbbell(1)6 and Ball(1)12 markedly inhibited the cytotoxic activity of both Stx1 (0.22 and 0.16 μg/ml respectively) and Stx2 (2.3 and 1.3 μg/ml, respectively) toward Vero cells; whereas the IC50 of Fan(0)3 was more than 100 μg/ml. The result of the binding assay of these toxins suggested that Dumbbell(1)6 and Ball(1)12 bind to both Stx1 and Stx2 with high affinities. Furthermore, inhibitory effects of these dendrimers on the lethality of intravenously administered Stx2 in mice were investigated. Dumbbell(1)6 completely suppressed the lethal effect of Stx2 when administered along with the toxin. The dendrimer treated mice survived more than 2 months without any pathological symptoms.
Japanese
ISSN：1880-4446,
CiNii Articles ID：120001370805 Synthesis of a useful lauryl thioglycoside of sialic acid and its application K Matsuoka; T Onaga; T Mori; JI Sakamoto; T Koyama; N Sakairi; K Hatano; D Terunuma
TETRAHEDRON LETTERS,
Volume：45,
Number：51,
First page：9383,
Last page：9386, Dec. 2004
An efficient synthesis of a useful thioglycosyl donor 2 was accomplished directly from known peracetylated sialic acid methvl ester and 1-dodecanethiol (lauryl mercaptan) in the presence of BF3-OEt2. The reactivities of the lauryl glycosides for glycosidation by means of TMSOTf as a convenient promoter were investigated, and the lauryl thioglycoside showed satisfactory activities. Further transformation of the lauryl glycoside was also attempted to give a 5-azide analogue 14 of the sialic acid, which was also reacted with a secondary alcohol in the presence of TMSOTf to give known glycoside 15 in high yield. (C) 2004 Elsevier Ltd. All rights reserved.
PERGAMON-ELSEVIER SCIENCE LTD, English
DOI：https://doi.org/10.1016/j.tetlet.2004.10.105DOI ID：10.1016/j.tetlet.2004.10.105,
ISSN：0040-4039,
CiNii Articles ID：80017025809,
Web of Science ID：WOS:000225648700017 Synthesis and biological evaluation of glycopolymer as Shiga toxin neutralizer
K Matsuoka; A Miyagawa; K Nishikawa; M Watanabe; Y Natori; E Kita; T Koyama; K Hatano; D Terunuma
GLYCOBIOLOGY, Volume：14, Number：11, First page：1194, Last page：1194, Nov. 2004
OXFORD UNIV PRESS INC, English, Summary international conference
ISSN：0959-6658, Web of Science ID：WOS:000224206400508
Synthesis and Property of Carbosilane Dendrimers Functionalizing Peripheral Mannose Moieties
T. Mori; K. Hatano; K. Matsuoka; Y. Esumi; E. J. Toone; D. Terunuma
Glycobiology, Volume：14, First page：1093, 2004
Glyco-silicon functional materials. Part 6. Synthesis of a useful anomeric thioacetate of an N-acetyllactosamine derivative and its application K Matsuoka; T Ohtawa; H Hinou; T Koyama; Y Esumi; SI Nishimura; K Hatano; D Terunuma
TETRAHEDRON LETTERS,
Volume：44,
Number：18,
First page：3617,
Last page：3620, Apr. 2003
A novel anomeric beta-thioacetate of an N-acetyllactosamine derivative was efficiently synthesized in high yield from the known 2-azido glycosyl chloride using thioacetic acid as a convenient reagent. The synthesis involved not only an S,2 replacement of the chloride by a carbothiolate anion but also a reductive acetamidation of the azide group. Applications of the thioacetate for glycosidation were demonstrated to provide both O- and S-glycosides in high yields. Furthermore, both intermediates gave a new class of glycoclusters that included thioglycosidic linkages. (C) 2003 Elsevier Science Ltd. All rights reserved.
PERGAMON-ELSEVIER SCIENCE LTD, English
DOI：https://doi.org/10.1016/S0040-4039(03)00697-XDOI ID：10.1016/S0040-4039(03)00697-X,
ISSN：0040-4039,
CiNii Articles ID：120001370836,
Web of Science ID：WOS:000182496400006 新規カルボシランデンドリマーの合成とその構造が液晶性に与える効果 土田隆樹; 島崎智恵美; 幡野健; 松岡浩司; 青木良夫; 野平博之; 江角保明; 照沼大陽
高分子論文集,
Volume：60,
Number：10,
First page：561,
Last page：568, 2003
DOI：https://doi.org/10.1295/koron.60.561DOI ID：10.1295/koron.60.561,
ISSN：0386-2186,
CiNii Articles ID：10012446351 Synthesis of Kinetically Stabilized Silaneselone and Silanetellone
TOKITOH Norihiro; SADAHIRO Tomonori; HATANO Ken; SASAKI Takayo; TAKEDA Nobuhiro; OKAZAKI Renji
Volume：2002, Number：1, First page：34, Last page：35, 05 Jan. 2002
English
ISSN：0366-7022, CiNii Articles ID：10009618528, CiNii Books ID：AA00603318
The first stable heteracyclopropabenzene: Synthesis and crystal structure of a silacyclopropabenzene K Hatano; N Tokitoh; N Takagi; S Nagase
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
Volume：122,
Number：19,
First page：4829,
Last page：4830, May 2000
AMER CHEMICAL SOC, English
DOI：https://doi.org/10.1021/ja000501kDOI ID：10.1021/ja000501k,
ISSN：0002-7863,
CiNii Articles ID：80011785034,
Web of Science ID：WOS:000087118100043 The first stable heteracyclopropabenzene: Synthesis and crystal structure of a silacyclopropabenzene K Hatano; N Tokitoh; N Takagi; S Nagase
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
Volume：122,
Number：19,
First page：4829,
Last page：4830, May 2000
AMER CHEMICAL SOC, English
DOI：https://doi.org/10.1021/ja000501kDOI ID：10.1021/ja000501k,
ISSN：0002-7863,
CiNii Articles ID：80011785034,
Web of Science ID：WOS:000087118100043 Steric stabilization of nucleophilic carbenes
MK Denk; A Thadani; K Hatano; AJ Lough
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, Volume：36, Number：23, First page：2607, Last page：2609, Dec. 1997
WILEY-V C H VERLAG GMBH, English
ISSN：1433-7851, Web of Science ID：WOS:000071234500008
Steric stabilization of nucleophilic carbenes
MK Denk; A Thadani; K Hatano; AJ Lough
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, Volume：36, Number：23, First page：2607, Last page：2609, Dec. 1997
WILEY-V C H VERLAG GMBH, English
ISSN：1433-7851, Web of Science ID：WOS:000071234500008
SYNTHESIS AND REDUCTION OF THE 9,10-DISILAANTHRACENE DIMER W ANDO; K HATANO; R URISAKA
ORGANOMETALLICS,
Volume：14,
Number：8,
First page：3625,
Last page：3627, Aug. 1995
9,10-Dimethyl-9,10-disilaanthracene dimer (2) was prepared by treatment of 9,10-dihydro-9,10-disilaanthracene (1a) with 2 equiv of lithium. The reaction of 2 with excess lithium or potassium resulted in formation, of 9,10-dilithio- or 9,10-dipotassio-9,10-dimethyl-9,10-disilaanthracene (4a,b), via the dianion 3, in which one Si-Si bond has been cleaved. On. treatment with alpha,omega-dichloropolysilanes, 4a was converted into the corresponding cyclic compounds 6-9, respectively.
AMER CHEMICAL SOC, English, Introduction scientific journal
DOI：https://doi.org/10.1021/om00008a007DOI ID：10.1021/om00008a007,
ISSN：0276-7333,
CiNii Articles ID：80008489557,
Web of Science ID：WOS:A1995RQ47100007
シロールをコアとする糖鎖担持カルボシランデンドリマーの合成とその光学特性の調査
2009
シロキサン類を集積場に用いた糖鎖クラスター化合物の合成
2009
シロールをコアとした糖鎖担持カルボシランデンドリマーによるレクチン検出評価
2009
Poster presentation
シロールをコアとする糖鎖担持カルボシランデンドリマーの合成とその光学特性の調査
日本化学会第89回春季年会講演予稿集, 2009
シロキサン類を集積場に用いた糖鎖クラスター化合物の合成
日本化学会第89回春季年会講演予稿集, 2009
シロールをコアとした糖鎖担持カルボシランデンドリマーによるレクチン検出評価
日本化学会第89回春季年会講演予稿集, 2009
Poster presentation
シロール含有糖鎖担持カルボシランデンドリマーに関する研究
2008
Poster presentation
機能性糖鎖を表面に修飾したシリカ微粒子の調製と評価
2008
Poster presentation
機能性糖鎖で修飾した発光物質含有有機微粒子の合成
2008
Poster presentation
糖鎖修飾型デンドリマーの分子認識蛍光試剤への応用:水中及び有機溶剤中における蛍光強度の変化と凝集状態の観測
2008
Poster presentation
Synthesis and Lectin-binding Activities of Carbohydrate-modified Polysiloxanes
2008
Poster presentation
Syntheses and Photoluminescence of Silole Core Carbosilane Dendrimers Peripheral Functionalize with Carbohydrates
2008
Poster presentation
Highly luminescent glycocluster in organic solvent: silole-core carbosilane dendrimer having peripheral globotriaose
2008
Poster presentation
機能性糖鎖を表面に修飾したシリカ微粒子の調製と評価
2008
Poster presentation
機能性糖鎖で修飾した発光物質含有有機微粒子の一段階合成
2008
Poster presentation
シロール含有糖鎖担持カルボシランデンドリマーに関する研究
第3回バイオ関連化学合同シンポジウム予稿集, 2008
Poster presentation
機能性糖鎖を表面に修飾したシリカ微粒子の調製と評価
第3回バイオ関連化学合同シンポジウム予稿集, 2008
Poster presentation
機能性糖鎖で修飾した発光物質含有有機微粒子の合成
第3回バイオ関連化学合同シンポジウム予稿集, 2008
Poster presentation
糖鎖修飾型デンドリマーの分子認識蛍光試剤への応用:水中及び有機溶剤中における蛍光強度の変化と凝集状態の観測
第3回バイオ関連化学合同シンポジウム予稿集, 2008
Poster presentation
Synthesis and Lectin-binding Activities of Carbohydrate-modified Polysiloxanes
Post ISOS XV Symposium Abstracts, 2008
Poster presentation
Syntheses and Photoluminescence of Silole Core Carbosilane Dendrimers Peripheral Functionalize with Carbohydrates
Post ISOS XV Symposium Abstracts, 2008
Poster presentation
Highly luminescent glycocluster in organic solvent: silole-core carbosilane dendrimer having peripheral globotriaose
Post ISOS XV Symposium Abstracts, 2008
Poster presentation
機能性糖鎖を表面に修飾したシリカ微粒子の調製と評価
57回高分子学会年次大会予稿集, 2008
Poster presentation
機能性糖鎖で修飾した発光物質含有有機微粒子の一段階合成
57回高分子学会年次大会予稿集, 2008
Poster presentation
Development of high-brightness luminescent beads using aggregation-induced emission materials and application to highly sensitive detection of viruses
Japan Society for the Promotion of Science, Grants-in-Aid for Scientific Research, Grant-in-Aid for Scientific Research (C), 01 Apr. 2017 - 31 Mar. 2020
Hatano Ken, Saitama University
Grant amount(Total)：4550000, Direct funding：3500000, Indirect funding：1050000
n this study, we have developed beads that emit light with high brightness by incorporating aggregation-induced emission materials into polystyrene beads. As a result, we were able to develop beads that emit light with high brightness, reaching a quantum yield of 90%. Further, using the beads as a core, surface functionalization, PEG chain modification, and sensitization with an anti-influenza antibody were performed to obtain a labeled antibody for an immunochromatography kit. Using this labeled antibody, an immunochromatography kit for influenza was prototyped. Comparing the detection sensitivity with a commercially available influenza immunochromatography kit that uses an antibody labeled with colloidal gold, it was found that the detection kit using the developed beads can detect influenza with 100 times higher sensitivity.
Grant number：17K01958
Development of one step synthesis of glycosyl acceptor substituted by overcrowded silyl group and regioselective glycosidation at 3-OH
Japan Society for the Promotion of Science, Grants-in-Aid for Scientific Research, Grant-in-Aid for Scientific Research (C), 01 Apr. 2013 - 31 Mar. 2016
HATANO Ken, Saitama University
Grant amount(Total)：5200000, Direct funding：4000000, Indirect funding：1200000
Silylation of hydroxyl groups on monosaccharides and lactose were obtained in good yield by one step reaction. In the case of lactose, the silylation occurred on 6, 2' and 6' positions of hydroxyl groups and the trisilylated lactose was able to isolate by recrystallization. Regioselective glycosydation at 3-OH (however 3'-OH in the case of lactose) of the silylated saccharides with a glucose derivative as a glycosyl donor were observed.
Grant number：25410170
Development of Carbohydrate-Silicon Functional Material to Detect Avian Influenza Virus
Japan Society for the Promotion of Science, Grants-in-Aid for Scientific Research, Grant-in-Aid for Scientific Research (C), 2009 - 2011
HATANO Ken, Saitama University
Grant amount(Total)：4940000, Direct funding：3800000, Indirect funding：1140000
We succeeded a synthesis of a novel carbosilane dendrimer functionalized aggregation-induced emission (AIE) active 2, 3, 4, 5 tetraphenyl1silacyclo-pentadiene at the core and periphery functionalized avian influenza virus binding 3'-sialyllactose as an avian inluruenza detection agent. Detection test of the virus using the dendrimer prepared here is currently in progress.
Grant number：21550152
ケイ素橋頭位化合物の構造特性を活用した新規導電性高分子の開発に関する基礎研究
2004 - 2006
Grant amount(Total)：3600000, Direct funding：3600000
Grant number：16750026
Development of electroluminescence device containing water soluble polysilane and organic dyes in sol-gel glass
Japan Society for the Promotion of Science, Grants-in-Aid for Scientific Research, Grant-in-Aid for Scientific Research (B), 2002 - 2004
TERUNUMA Daiyo; KAMATA Norihiko; HATANO Ken; HONDA Zentaro, Saitama University
Grant amount(Total)：6200000, Direct funding：6200000
It is known that polysilanes display unique characteristics such as UV absorption, photo-, and electroluminescence due to σ-conjugation of the Si-Si main chain. We have been studied the preparation of new water-soluble polysilane, the energy transfer and radiative properties of polysilanes, and energy-matched counterparts. And, it was found that photo-oxidation during irradiation an ultraviolet light was suppressed by using water-soluble polysilanes and embedding them inside sol-gel glass matrices. However, there are problems for the preparation of watersoluble polysilanes, because Wurtz type reaction usually gives only a low yield. So, it is important to improve the way for the synthesis of water-soluble polysilanes.
We have interested in the use of commercially available dodecaphenylcyclopentasilane(DPCPS). DPCPS was treated with Li in tetrahydrofuran to give ring opening intermediate ; α, ω-dilithiododecaphenylpetasilane. Reaction of the intermediate with an equimolecular amount of dichlorodimethylsilane afforded cyclic polysilanes, resulted from intramolecular cyclization reaction, and a small amount of low molecular-weight polymer. On the other hand, the treatment of the intermediate with an equimolecular amount of 1,2-dichlorotetramethyldisilane gave higher molecular weight polysilane co-polymer as a result of predominant intermolecular reaction.
The obtained co-polymer was successfully converted into water-soluble polysilane derivative by successive Friedel-Crafts chloromethylation and quaternary ammonium reaction.
The intermolecular energy transfer from conductive poly(m-hexoxyphenyl)phenylsilane was utilized for electroluminescence(EL) of perylene (blue), coumarin 6 (green), 4-(dicyanometliylene)-2-methyl-6-(p-dimethylammostyryl)-4H-pyran and Zinc tetra-phenylporphyrin (red). A white EL was also observed by mixing the four dyes. Photo-oxidation during irradiating a ultraviolet light was suppressed by synthesizing water-soluble polysilanes and embedding it inside sol-gel glass matrices. These results imply that polysilanes have a possibility to open new fields of optical application.
Grant number：14350158
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Competitive research funding
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Competitive research funding
