Study for elucidation of the structures and functions of nano-sized membrane domains using glycolipid probes

• Project/Area Number: 15H04495
• Research Category: Grant-in-Aid for Scientific Research (B)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Bioorganic chemistry
• Research Institution: Gifu University
• Principal Investigator: ANDO Hiromune 岐阜大学, 研究推進・社会連携機構, 教授 (20372518)
• Co-Investigator(Renkei-kenkyūsha): SUZUKI Kenichi 岐阜大学, 研究推進・社会連携機構, 教授 (50423059)
• Project Period (FY): 2015-04-01 – 2018-03-31
• Project Status: Completed (Fiscal Year 2017)
• Budget Amount: ¥16,900,000 (Direct Cost: ¥13,000,000、Indirect Cost: ¥3,900,000); Fiscal Year 2017: ¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000); Fiscal Year 2016: ¥5,460,000 (Direct Cost: ¥4,200,000、Indirect Cost: ¥1,260,000); Fiscal Year 2015: ¥7,280,000 (Direct Cost: ¥5,600,000、Indirect Cost: ¥1,680,000)
• Keywords: 細胞膜ドメイン / 脂質ラフト / ガングリオシド / 1分子イメージング / 糖鎖 / 一分子イメージング / 有機合成 / 光応答性プローブ

Outline of Final Research Achievements

Research aim: To figure out the mechansims of the formation of the tentatively formed cell membrane domains by the single molecule imaging tequnique. This research mainly focuses on the behavior of glycolipids, which are key components of the cell membrane domains.

Research outcomes: A series of the fluorescent labeled glycolipids which are useful as equivalents to native molecules has been developed for the first time. We have found the molecular interactions fundamental and essential for the formations of lipid raft and glycolipid domain by the single molecule imaging technique.

Research Products

• [Journal Article] Revealing the raft domain organization in the plasma membrane by single-molecule imaging of fluorescent ganglioside analogs. (2018)
  • Author(s): Kenichi G. N. Suzuki, Hiromune Ando, Naoko Komura, Akihiro Imamura, Hideharu Ishida, Makoto Kiso, Takahiro K. Fujiwara, Akihiro Kusumi.
  • Journal Title: Methods in Enzymology Volume: 598 Pages: 267-282
  • DOI: 10.1016/bs.mie.2017.06.038
  • Peer Reviewed
• [Journal Article] Synthesis and Functional Characterization of Novel Sialyl LewisX Mimic-Decorated Liposomes for E-selectin-Mediated Targeting to Inflamed Endothelial Cells (2017)
  • Author(s): Chantarasrivong Chanikarn、Ueki Akiharu、Ohyama Ryutaro、Unga Johan、Nakamura Shinya、Nakanishi Isao、Higuchi Yuriko、Kawakami Shigeru、Ando Hiromune、Imamura Akihiro、Ishida Hideharu、Yamashita Fumiyoshi、Kiso Makoto、Hashida Mitsuru
  • Journal Title: Molecular Pharmaceutics Volume: 14 Issue: 5 Pages: 1528-1537
  • DOI: 10.1021/acs.molpharmaceut.6b00982
  • Peer Reviewed
• [Journal Article] A 1,2-trans-Selective Glycosyl Donor Bearing Cyclic Protection at the C-2 and C-3 Hydroxy Groups (2017)
  • Author(s): Yagami Nahoko、Tamai Hideki、Udagawa Taro、Ueki Akiharu、Konishi Miku、Imamura Akihiro、Ishida Hideharu、Kiso Makoto、Ando Hiromune
  • Journal Title: European Journal of Organic Chemistry Volume: 2017 Issue: 32 Pages: 4778-4785
  • DOI: 10.1002/ejoc.201700671
  • Peer Reviewed
• [Journal Article] Synthesis of fluorescent gangliosides for the studies of raft domains. (2017)
  • Author(s): Naoko Komura, Kenichi G. N. Suzuki, Hiromune Ando, Miku Konishi, Akihiro Imamura, Hideharu Ishida, Akihiro Kusumi, Makoto Kiso.
  • Journal Title: Methods in Enzymology Volume: 597 Pages: 239-263
  • DOI: 10.1016/bs.mie.2017.06.004
  • Peer Reviewed
• [Journal Article] Development of new ganglioside probes and unraveling of raft domain structure by single-molecule imaging. (2017)
  • Author(s): Kenichi G. N. Suzuki, Hiromune Ando, Naoko Komura, Takahiro K. Fujiwara, Makoto Kiso, Akihiro Kusumi.
  • Journal Title: Biochim. Biophys. Acta Volume: 1861 Issue: 10 Pages: 2494-2506
  • DOI: 10.1016/j.bbagen.2017.07.012
  • Peer Reviewed
• [Journal Article] A Synthetic Challenge to the Diversity of Gangliosides for Unveiling Their Biological Significance (2017)
  • Author(s): Ando, H., Komura, N., Imamura, A., Kiso, M., Ishida, H.
  • Journal Title: Journal of Synthetic Organic Chemistry, Japan Volume: 75 Issue: 11 Pages: 1162-1170
  • DOI: 10.5059/yukigoseikyokaishi.75.1162
  • NAID: 130006196292
  • ISSN: 0037-9980, 1883-6526
  • Peer Reviewed / Open Access
• [Journal Article] Synthesis of seleno-fucose compounds and their application to the X-ray structural determination of carbohydrate-lectin complexes using single/multi-wavelength anomalous dispersion phasing. (2017)
  • Author(s): J. Shimabukuro, H. Makyio, T. Suzuki, Y. Nishikawa, M. Kawasaki, A. Imamura, H. Ishida, H. Ando, R. Kato, M. Kiso
  • Journal Title: Bioorg. Med. Chem. Volume: 25 Issue: 3 Pages: 1132-1142
  • DOI: 10.1016/j.bmc.2016.12.021
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Raft-based interactions of gangliosides with a GPI-anchored receptor (2016)
  • Author(s): N. Komura, K. G. N. Suzuki, H. Ando, M. Konishi, M. Koikeda, A. Imamura, R. Chadda, T. K. Fujiwara, H. Tsuboi, R. Sheng, W. Cho, K. Furukawa, K. Furukawa, Y. Yamauchi, H. Ishida, A. Kusumi (Co-Corresponding Author), and M. Kiso
  • Journal Title: Nat. Chem. Biol. Volume: in press Issue: 6 Pages: 402-410
  • DOI: 10.1038/nchembio.2059
  • Peer Reviewed / Open Access / Int'l Joint Research
• [Journal Article] Efficient synthesis of the Lewis A tandem repeat for elucidating the carbohydrate recognition mechanism of mannose binding protein (2016)
  • Author(s): D. Kobayashi, A. Ueki, T. Yamaji, K. Nagao, A. Imamura, H. Ando, M. Kiso, H. Ishida
  • Journal Title: Molecules Volume: 21 Issue: 5 Pages: 614-614
  • DOI: 10.3390/molecules21050614
  • Peer Reviewed / Open Access / Acknowledgement Compliant
• [Journal Article] First total synthesis of starfish ganglioside GP3 bearing a unique sialyl glycan structure (2016)
  • Author(s): K. Goto, M. Sawa, H. Tamai, A. Imamura, H. Ando, H. Ishida, M. Kiso
  • Journal Title: Chem. Eur. J. Volume: 22 Issue: 24 Pages: 8323-8331
  • DOI: 10.1002/chem.201600970
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] A novel potent and highly specific inhibitor against influenza viral N1-N9 neuraminidases: Insight into neuraminidase-inhibitor interactions (2016)
  • Author(s): N. Sriwilaijaroen, S. Magesh, A. Imamura, H. Ando, H. Ishida, M. Sakai, E. Ishitsubo, T. Hori, S. Moriya, T. Ishikawa, K. Kuwata, T. Odagiri, M. Tashiro, H. Hiramatsu, K. Tsukamoto, T. Miyagi, H. Tokiwa, M. Kiso, Y. Suzuki
  • Journal Title: J. Med. Chem. Volume: 59 Issue: 8 Pages: 4563-4577
  • DOI: 10.1093/glycob/cww060
  • Peer Reviewed
• [Journal Article] Six independent fucose-binding sites in the crystal structure of Aspergillus oryzae lectin (2016)
  • Author(s): H. Makyio, J. Shimabukuro, T. Suzuki, A. Imamura, H. Ishida, M. Kiso, H. Ando, R. Kato
  • Journal Title: Biochem. Biophys. Res. Commun. Volume: 477 Issue: 3 Pages: 477-482
  • DOI: 10.1016/j.bbrc.2016.06.069
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] The origin of high stereoselectivity in di-tert-butylsilylene-directed (2016)
  • Author(s): A. Imamura, N. Matsuzawa, S. Sakai, T. Udagawa, S. Nakashima, H. Ando, H. Ishida, M. Kiso
  • Journal Title: J. Org. Chem. Volume: 81 Issue: 19 Pages: 9086-9140
  • DOI: 10.1021/acs.joc.6b01685
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Ureido-Modified Sialyl Donor: A Tool for the Synthesis of (2016)
  • Author(s): M. Tanase, A. Imamura, H. Ando, H. Ishida, M. Kiso
  • Journal Title: Org. Lett. Volume: 18 Issue: 6 Pages: 1454-1457
  • DOI: 10.1021/acs.orglett.6b00403
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] First Total Synthesis of Ganglioside GAA-7 from Starfish Asterias amurensis versicolor (2015)
  • Author(s): Tamai, H., Imamura, A., Ogawa, J., Ando, H., Ishida, H. and Kiso, M.
  • Journal Title: Eur. J. Org. Chem. Volume: 8 Issue: 23 Pages: 5199-5211
  • DOI: 10.1002/ejoc.201500606
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Total Synthesis and Neuritogenic Activity Evaluation of Ganglioside PNG-2A from the Starfish Protoreaster nodosus (2015)
  • Author(s): Goto, K., Suzuki, T., Tamai, H., Ogawa, J., Imamura, A., Ando, H., Ishida, H. and Kiso, M.
  • Journal Title: Asian J. Org. Chem. Volume: 4 Issue: 10 Pages: 1160-1171
  • DOI: 10.1002/ajoc.201500282
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Total Syntheses of Disulphated Glycosphingolipid SB1a and the Related Monosulphated SM1a (2015)
  • Author(s): H. Hirose, H. Tamai, C. Gao, A. Imamura, H. Ando, H. Ishida, T. Feizi, M. Kiso
  • Journal Title: Org. Biomol. Chem. Volume: 13 Issue: 45 Pages: 11105-11117
  • DOI: 10.1039/c5ob01744k
  • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
• [Journal Article] Structure-Activity Relationship Study of the Neuritogenic Potential of the Glycan of Starfish Ganglioside LLG-3 (2015)
  • Author(s): M. Yamagishi, R. Hosoda-Yabe, H. Tamai, M. Konishi, A. Imamura, H. Ishida, T. Yabe, H. Ando, M. Kiso
  • Journal Title: Mar. Drugs Volume: 13 Issue: 12 Pages: 7250-7274
  • DOI: 10.3390/md13127062
  • NAID: 120005756289
  • Peer Reviewed / Open Access / Acknowledgement Compliant
• [Presentation] 糖鎖の構造多様性に挑む－精密合成が拓く糖鎖の機能研究－ (2017)
  • Author(s): 安藤弘宗
  • Organizer: 平成29年度有機合成セミナー
  • Invited
• [Presentation] Synthetic chemistry of sialic acid-containing glycolipids for molecular understanding of their biological roles (2017)
  • Author(s): Ando, H
  • Organizer: International Symposium on Pure & Applied Chemistry 2017 (ISPAC2017)
  • Int'l Joint Research / Invited
• [Presentation] Development of structurally defined fluorescent probes of glycosphingolipids useful for lipid raft research (2017)
  • Author(s): Ando, H
  • Organizer: International seminar on biophysics and chemical biology of biomembrane and lipid bilayers
  • Int'l Joint Research / Invited
• [Presentation] 糖鎖機能の分子理解を指向した分子創製 (2017)
  • Author(s): 安藤弘宗
  • Organizer: 第44回有機典型元素化学討論会
  • Invited
• [Presentation] 精密有機合成を基盤とした細胞膜微小領域の分子基盤研究 (2017)
  • Author(s): 安藤弘宗
  • Organizer: 理研シンポジウム 「細胞内糖修飾の統合的ケミカルバイオロジー」
  • Invited
• [Presentation] Synthesis of fluorescent probes of globo-series gangliosides (2017)
  • Author(s): Asano, S., Yamaguchi, E., Komura, N., Ando, H., Imamura, A., Ishida, H., Kiso, M.
  • Organizer: 19th European Carbohydrate Symposium, Barcelona
  • Int'l Joint Research
• [Presentation] グロボ系ガングリオシドの膜ドメイン形成機構解明を目指した蛍光アナログ分子の開発 (2017)
  • Author(s): 浅野早知、河村奈緒子、今村彰宏、石田秀治、安藤弘宗
  • Organizer: 糖鎖科学中部拠点 第14回「若手の力」フォーラム
• [Presentation] 1,2-trans-Selective glycosyl donor bearing cyclic protection at the C2 and C3 hydroxyl groups (2017)
  • Author(s): Yagami, N. Tamai, H., Ueki, A., Konishi, M., Ando, H., Imamura, A., Ishida, H., Kiso, M.:
  • Organizer: 19th European Carbohydrate Symposium
  • Int'l Joint Research
• [Presentation] Molecular interactions in the cell membrane revealed by novel glycolipid probes (2016)
  • Author(s): H. Ando
  • Organizer: CARBO-XXXI: 2016, An International Conference on New Frontiers in Carbohydrate Chemistry and Biology
  • Place of Presentation: Delhi, India
  • Year and Date: 2016-11-14
  • Int'l Joint Research / Invited
• [Presentation] 新しい糖鎖プローブで追う脂質ラフトの実体 (2016)
  • Author(s): 安藤弘宗
  • Organizer: 第25回日本バイオイメージング学会学術集会
  • Place of Presentation: 名古屋市
  • Year and Date: 2016-09-04
  • Invited
• [Presentation] 神経突起伸展活性を有するウミシダ由来シアル酸含有糖脂質 CJP 系列の 全合成 (2016)
  • Author(s): 玉井秀樹, 後藤健太, 武田陽, 水野孝星, 安藤弘宗, 今村彰宏, 石田秀治, 木曽真
  • Organizer: 第35回日本糖質学会年会
  • Place of Presentation: 高知市
  • Year and Date: 2016-08-31
• [Presentation] ラフト分子の1分子イメージングに向けた蛍光ガングリオシドの開発 (2016)
  • Author(s): 河村奈緒子, 鈴木健一, 安藤弘宗, 小西美紅, 今村彰宏, 石田秀治, 楠見明弘, 木曽真:
  • Organizer: 第35回日本糖質学会年会
  • Place of Presentation: 高知市
  • Year and Date: 2016-08-31
• [Presentation] Synthetic study on unique sialic acid containing glycan architectures of neuritogenic gangliosides found in echinoderms (2016)
  • Author(s): H. Ando, H. Tamai, T. Suzuki, A. Imamura, H. Ishida, M. Kiso
  • Organizer: 2016 International Carbohydrate Symposium (ICS2016)
  • Place of Presentation: New Orleans, USA
  • Year and Date: 2016-07-17
  • Int'l Joint Research
• [Presentation] Development of fluorescent ganglioside analogs for imaging of raft-based interactions. (2016)
  • Author(s): Komura, N., Suzuki, K., Ando, H., Konishi, M., Imamura, A., Ishida, H., Kusumi, A., Kiso, M
  • Organizer: 2016 International Carbohydrate Symposium (ICS2016)
  • Place of Presentation: New Orleans, USA
  • Year and Date: 2016-07-17
  • Int'l Joint Research
• [Presentation] Synthetic chemistry challenging to diversity of gangliosides (2016)
  • Author(s): H. Ando
  • Organizer: The 3rd International Symposium on Glyco-Neuroscience
  • Place of Presentation: 淡路市
  • Year and Date: 2016-07-14
  • Int'l Joint Research / Invited
• [Presentation] Development of novel ganglioside probes to explore glycan-protein architecture formed in the cell membrane (2016)
  • Author(s): H. Ando
  • Organizer: Glycoscience Japan -The Netherlands Joint seminar 2016
  • Place of Presentation: Leiden, The Netherland
  • Year and Date: 2016-04-20
  • Int'l Joint Research / Invited
• [Presentation] 脂質ラフトの一分子イメージングに向けたGPIアンカープローブの合成研究 (2016)
  • Author(s): 小西美紅, 鈴木達哉, Rita, P., 安藤弘宗, 今村彰宏, 石田秀治, 木曽真
  • Organizer: 日本農芸化学会2016年度大会
  • Place of Presentation: 札幌
  • Year and Date: 2016-03-27
• [Presentation] 脂質ラフトの機能解明に向けた光反応性ガングリオシドプローブの開発 (2016)
  • Author(s): 河村奈緒子, 鈴木健一, 安藤弘宗, 今村彰宏, 石田秀治, 楠見明弘, 木曽真
  • Organizer: 日本農芸化学会2016年度大会
  • Place of Presentation: 札幌
  • Year and Date: 2016-03-27
• [Presentation] 脂質ラフトの一分子観察に向けた脂質および糖鎖変換型蛍光GM3プローブの合成と機能評価 (2016)
  • Author(s): 山﨑彩乃, 河村奈緒子, 鈴木健一, 安藤弘宗, 今村彰宏, 石田秀治, 楠見明弘, 木曽真
  • Organizer: 日本農芸化学会2016年度大会
  • Place of Presentation: 札幌
  • Year and Date: 2016-03-27
• [Presentation] 脂質ラフトの一分子観察に向けた蛍光ラクトシルセラミドの合成 (2016)
  • Author(s): 山口英利子, 河村奈緒子, 鈴木健一, 安藤弘宗, 今村彰宏, 石田秀治, 楠見明弘, 木曽真
  • Organizer: 日本農芸化学会2016年度大会
  • Place of Presentation: 札幌
  • Year and Date: 2016-03-27
• [Presentation] 合成化学で糖鎖の新世界を探訪する (2016)
  • Author(s): 安藤弘宗
  • Organizer: 第10回多糖の未来フォーラム
  • Place of Presentation: 名古屋市
  • Invited
• [Presentation] Ganglioside probes for exploring functional molecular complexes in the cell membrane (2015)
  • Author(s): Ando, Hiromune:
  • Organizer: The 2015 International Chemical Congress of Pacific Basin Societies (PACIFICHEM2015)
  • Place of Presentation: ハワイ
  • Year and Date: 2015-12-15
  • Int'l Joint Research / Invited
• [Presentation] Total synthesis of ganglioside PNG-2A found in the starfish Protoreaster nodosus. (2015)
  • Author(s): Goto, K., Suzuki, T., Tamai, H., Ogawa, J., Ando, H., Imamura, A., Ishida, H., Kiso, M.
  • Organizer: The 2015 International Chemical Congress of Pacific Basin Societies (PACIFICHEM2015)
  • Place of Presentation: ハワイ
  • Year and Date: 2015-12-15
  • Int'l Joint Research
• [Presentation] Ganglioside synthesis for understanding interplays with membrane molecules. (2015)
  • Author(s): Ando, Hiromune
  • Organizer: 2015 Glycoscience Symposium, Institute of Biological Chemistry, Academia Sinica
  • Place of Presentation: 台湾
  • Year and Date: 2015-12-07
  • Int'l Joint Research / Invited
• [Presentation] 糖鎖-蛋白質複合体の機能解明を指向したガングリオシドプローブの開発 (2015)
  • Author(s): 安藤弘宗
  • Organizer: 第34回日本糖質学会年会
  • Place of Presentation: 東京
  • Year and Date: 2015-07-31
  • Invited
• [Book] Organoselenium Compounds in Biology and Medicine: Synthesis, Biological and TherapeuticTreatments (2017)
  • Author(s): Kona, C., Shimabukuro, J., Kiso, M., Ando, H.
  • Total Pages: 457
  • Publisher: the Royal Society of Chemistry
• [Book] 糖鎖の新機能開発・応用ハンドブック 創薬・医療から食品開発まで (2015)
  • Author(s): 安藤弘宗, 鈴木健一, 楠見明弘, 木曾眞
  • Total Pages: 678
  • Publisher: (株)エヌ・ティー・エス
• [Book] 糖鎖の新機能開発・応用ハンドブック 創薬・医療から食品開発まで (2015)
  • Author(s): 今村彰宏, 安藤弘宗, 石田秀治, 木曾眞
  • Total Pages: 678
  • Publisher: (株)エヌ・ティー・エス
• [Remarks] https://www1.gifu-u.ac.jp/~kassei1/
• [Remarks] http://www1.gifu-u.ac.jp/~kassei1/