論文 - 松原　輝彦

Amyloid- fibrils assembled on ganglioside-enriched membranes contain both parallel -sheets and turns

Matsubara T., Yasumori H., Ito K., Shimoaka T., Hasegawa T., Sato T.

Journal of Biological Chemistry （Journal of Biological Chemistry）  293 （ 36 ） 14146 - 14154 2018年09月

ISSN  00219258

　概要を見る

Some protein and peptide aggregates, such as those of amyloid- protein (A), are neurotoxic and have been implicated in several neurodegenerative diseases. A accumulates at nanoclusters enriched in neuronal lipids called gangliosides in the presynaptic neuronal membrane, and the resulting oligomeric and/or fibrous forms accelerate the development of Alzheimer’s disease. Although the presence of A deposits at such nanoclusters is known, the mechanism of their assembly and the relationship between A secondary structure and topography are still unclear. Here, we first confirmed by atomic force microscopy that A40 fibrils can be obtained by incubating seed-free A40 monomers with a membrane composed of sphingomyelin, cholesterol, and the ganglioside GM1. Using Fourier transform infrared (FTIR) reflection–absorption spectroscopy, we then found that these lipid-associated fibrils contained parallel -sheets, whereas self-assembled A40 molecules formed antiparallel -sheets. We also found that the fibrils obtained at GM1-rich nanoclusters were generated from turn A40. Our findings indicate that A generally self-assembles into antiparallel -structures but can also form protofibrils with parallel -sheets by interacting with ganglioside-bound A. We concluded that by promoting the formation of parallel -sheets, highly ganglioside-enriched nanoclusters help accelerate the elongation of A fibrils. These results advance our understanding of ganglioside-induced A fibril formation in neuronal membranes and may help inform the development of additional therapies for Alzheimer’s disease.

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Izenamides A and B, Statine-Containing Depsipeptides, and an Analogue from a Marine Cyanobacterium

Kanamori Y., Iwasaki A., Sumimoto S., Matsubara T., Sato T., Suenaga K.

Journal of Natural Products （Journal of Natural Products）  81 （ 7 ） 1673 - 1681 2018年07月

ISSN  01633864

　概要を見る

Izenamides A, B, and C (1-3), new linear depsipeptides, were isolated from a taxonomically distinct marine cyanobacterium. Izenamides A and B contain a statine moiety [(3S,4S)-4-amino-3-hydroxy-6-methylheptanoic acid] and inhibited the activity of cathepsin D, an aspartic peptidase. Meanwhile, izenamides did not show growth-inhibitory activity against HeLa, HL60, or MCF-7 cells at up to 10 μM.

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Responsibility of lipid compositions for the amyloid ß assembly induced by ganglioside nanoclusters in mouse synaptosomal membranes

Matsubara T., Kojima T., Fukuda R., Iijma K., Hirai M., Yamamoto N., Yanagisawa K., Sato T.

Polymer Journal （Polymer Journal）  50 （ 8 ） 745 - 752 2018年03月

研究論文（学術雑誌）, 共著, 査読有り,  ISSN  00323896

　概要を見る

The assembly of amyloid ß protein (Aß) on ganglioside-enriched microdomains in presynaptic neuronal membranes is involved in the onset of Alzheimer’s disease. We previously found that a highly enriched ganglioside domain generated in a reconstituted lipid bilayer composed of synaptosomal lipids functioned as an Aß-sensitive ganglioside nanocluster (ASIGN) that may induce a spherical Aß assembly. In the present study, the major lipid components of a detergent-resistant membrane microdomain (DRM) fraction of synaptosomes prepared from an aged mouse brain were identified, and we demonstrate that the proportion of Aß-insensitive gangliosides such as GM3 directly affects the Aß assembly in synaptosomal membranes. Liquid chromatography coupled to mass spectrometry analyses indicated that ganglio a-series gangliosides (GM1, GM2, GM3, and GD1a) were abundant in DRM fractions. In addition, the GM3/GM1 ratio and the cholesterol content in the synaptosomal fraction differed from those in the non-synaptosomal fraction, in which GM1 and GM3 are sensitive and insensitive gangliosides, respectively. The highly enriched ganglioside nanocluster was identified by the surface topography of ternary mixed lipid bilayers composed of gangliosides, sphingomyelin, and cholesterol. Our results indicate that the composition of gangliosides is responsible for the characteristics of the nanocluster generated in the presynaptic neuronal membranes.

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Novel hemagglutinin-binding sulfated oligofucosides and their effect on influenza virus infection

Kosono S., Kasai A., Komaba S., Matsubara T., Sato T., Takahashi D., Toshima K.

Chemical Communications （Chemical Communications）  54 （ 54 ） 7467 - 7470 2018年

ISSN  13597345

　概要を見る

Among a series of chemically synthesized fucoidan derivatives (1-9), 5 was found for the first time to bind to influenza virus hemagglutinins (HAs) and inhibit hemagglutination activity. In addition, a designed C3-symmetric tripodal ligand 10, synthesized with three sulfated oligofucoside moieties of 5, exhibited much greater hemagglutination inhibition activity than 5. A plaque assay using MDCK cells demonstrated that 10 effectively inhibited influenza virus infection.

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Size and shape of amyloid fibrils induced by ganglioside nanoclusters: role of sialyl oligosaccharide in fibril formation

Teruhiko Matsubara, Masaya Nishihara, Hanaki Yasumori, Mako Nakai, Katsuhiko Yanagisawa, Toshinori Sato

Langmuir 33 （ 48 ） 13874 - 13881 2017年11月

研究論文（学術雑誌）, 共著, 査読有り

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Design of glycopolymers carrying sialyl oligosaccharides for controlling the interaction with the influenza virus

Masanori Nagao, Yurina Fujiwara, Teruhiko Matsubara, Yu Hoshino, Toshinori Sato, Yoshiko Miura

Biomacromolecules 18 （ 12 ） 4385 - 4392 2017年11月

研究論文（学術雑誌）, 共著, 査読有り

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Kohamamides A, B and C, Cyclic Depsipeptides from an Okeania sp. Marine Cyanobacterium

Arihiro Iwasaki, Ikuma Shiota, Shinpei Sumimoto, Teruhiko Matsubara, Toshinori Sato, Kiyotake Suenaga

J. Nat. Prod. 80 （ 6 ） 1948 - 1952 2017年05月

研究論文（学術雑誌）, 共著, 査読有り

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Selective Intracellular Delivery of Ganglioside GM3-Binding Peptide through Caveolae/Raft-Mediated Endocytosis

Teruhiko Matsubara, Ryohei Otani, Miki Yamashita, Haruka Maeno, Hanae Nodono, and Toshinori Sato

Biomacromolecules 18 （ 2 ） 355 - 362 2017年01月

研究論文（学術雑誌）, 共著, 査読有り

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Highly sensitive detection of influenza virus by boron-doped diamond electrode terminated with sialic acid-mimic peptide.

Teruhiko Matsubara, Michiko Ujie, Takashi Yamamoto, Miku Akahori, Yasuaki Einaga, Toshinori Sato

Proc. Natl. Acad. Sci. U.S.A. 113 （ 32 ） 8981 - 8984 2016年07月

研究論文（学術雑誌）, 共著, 査読有り

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Binding of hemagglutinin and influenza virus to a peptide-conjugated lipid membrane

Teruhiko Matsubara, Rabi Shibata, and Toshinori Sato

Front. Microbiol. 7 （ 468 ） 1 - 9 2016年04月

研究論文（学術雑誌）, 共著, 査読有り

Heptapeptide ligands against receptor-binding sites of influenza hemagglutinin toward anti-influenza therapy

Teruhiko Matsubara, Ai Onishi, Daisuke Yamaguchi, Toshinori Sato

Bioorg. Med. Chem. 24 （ 5 ） 1106 - 1114 2016年03月

研究論文（学術雑誌）, 共著, 査読有り

体液類似環境におけるアパタイト結合性ペプチド樹状オリゴマーによるミネラリゼーション

橋詰　峰雄, 小野上　綾乃, 飯島　一智, 松原　輝彦, 内田　祐樹, 佐藤　智典

高分子論文集 73 （ 1 ） 55 - 61 2016年01月

研究論文（学術雑誌）, 共著, 査読有り

糖鎖模倣ペプチドのインフルエンザヘマグルチニンに対する結合活性の多価効果

松原 輝彦, 大西 愛, 齋藤 智美, 山口 大介, 佐藤 智典

高分子論文集 73 （ 1 ） 62 - 68 2016年01月

研究論文（学術雑誌）, 共著, 査読有り

Mebamamides A and B, Cyclic Lipopeptides Isolated from the Green Alga Derbesia marina

Arihiro Iwasaki, Osamu Ohno, Shinpei Sumimoto, Teruhiko Matsubara, Satoshi Shimada, Toshinori Sato, Kiyotake Suenaga

J. Nat. Prod. 78 （ 4 ） 901 - 908 2015年04月

研究論文（学術雑誌）, 共著, 査読有り

Imbalance in fatty-acid-chain length of gangliosides triggers Alzheimer amyloid deposition in the precuneus

松原 輝彦

PLoS One 10 （ 3 ） e0121356 2015年03月

研究論文（学術雑誌）, 共著, 査読有り

Synthesis and influenza virus inhibitory activities of carbosilane dendrimers peripherally-functionalized with hemagglutinin-binding peptide

松原 輝彦

J. Med. Chem. 57 （ 20 ） 8332 - 8339 2014年10月

研究論文（学術雑誌）, 共著, 査読有り

細胞表面のオリゴ糖鎖の謎を解く分子を創る

松原 輝彦

化学と教育 61 （ 5 ） 234 - 235 2013年05月

研究論文（学術雑誌）, 単著

Density of GM1 in Nanoclusters Is a Critical Factor in the Formation of a Spherical Assembly of Amyloid β-Protein on Synaptic Plasma Membranes

Teruhiko Matsubara, Kazutoshi Iijima, Naoki Yamamoto, Katsuhiko Yanagisawa, and Toshinori Sato

Langmuir 29 （ 7 ） 2258-2264 2013年

研究論文（学術雑誌）, 共著, 査読有り

Incorporation of glycosylated amino acid into protein by an in vitro translation system

松原 輝彦

Bioorg. Med. Chem. Lett. 23 （ 20 ） 5634 - 5636 2013年

研究論文（学術雑誌）, 共著, 査読有り

Potential of peptides as inhibitors and mimotopes: selection of carbohydrate-mimetic peptides from phage display libraries

松原 輝彦

J. Nucleic Acids 740982   1-15 2012年

研究論文（学術雑誌）, 単著, 査読有り