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Development of Fluorescent Ganglioside GD3 and GQ1b Analogs for Elucidation of Raft-Associated Interactions

  • Miku Konishi
    Miku Konishi
    Center for Highly Advanced Integration of Nano and Life Sciences (G-CHAIN), Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan
    More by Miku Konishi
  • Naoko Komura*
    Naoko Komura
    Institute for Glyco-core Research (iGCORE), Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan
    Center for Highly Advanced Integration of Nano and Life Sciences (G-CHAIN), Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan
    *Email: [email protected]
    More by Naoko Komura
  • Yuya Hirose
    Yuya Hirose
    Department of Applied Bioorganic Chemistry, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan
    More by Yuya Hirose
  • Yuki Suganuma
    Yuki Suganuma
    Department of Applied Bioorganic Chemistry, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan
  • Hide-Nori Tanaka
    Hide-Nori Tanaka
    Institute for Glyco-core Research (iGCORE), Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan
    Center for Highly Advanced Integration of Nano and Life Sciences (G-CHAIN), Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan
  • Akihiro Imamura
    Akihiro Imamura
    Department of Applied Bioorganic Chemistry, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan
  • Hideharu Ishida
    Hideharu Ishida
    Institute for Glyco-core Research (iGCORE), Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan
    Center for Highly Advanced Integration of Nano and Life Sciences (G-CHAIN), Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan
    Department of Applied Bioorganic Chemistry, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan
  • Kenichi G. N. Suzuki*
    Kenichi G. N. Suzuki
    Institute for Glyco-core Research (iGCORE), Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan
    Center for Highly Advanced Integration of Nano and Life Sciences (G-CHAIN), Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan
    *Email: [email protected]
  • , and 
  • Hiromune Ando*
    Hiromune Ando
    Institute for Glyco-core Research (iGCORE), Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan
    Center for Highly Advanced Integration of Nano and Life Sciences (G-CHAIN), Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan
    *Email: [email protected]
Cite this: J. Org. Chem. 2020, 85, 24, 15998–16013
Publication Date (Web):September 21, 2020
https://doi.org/10.1021/acs.joc.0c01493
Copyright © 2020 American Chemical Society

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    Abstract

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    b-Series gangliosides are abundant in central nervous tissues and are involved in important nerve processes. However, their functions are complicated because of their properties of forming dynamic domains in cell plasma membranes (PMs), called lipid rafts. In this study, we aim to develop fluorescently labeled b-series gangliosides that are useful for single-molecule imaging. The chemical synthesis of fluorescent GD3 and GQ1b was achieved using sialylation and ganglioside synthetic methods previously developed by our group. Furthermore, biophysical evaluations demonstrated that synthesized fluorescent GD3 and GQ1b behaved as raft molecules on cell PMs, suggesting their applicability to the study of raft-associated interactions.

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    Cited By

    This article is cited by 13 publications.

    1. Zhongwu Guo. Synthetic glycosphingolipid probes and their biological application. 2024, 353-424. https://doi.org/10.1016/B978-0-443-16156-8.00008-0
    2. Kenichi G. N. Suzuki, Naoko Komura, Hiromune Ando. Recently developed glycosphingolipid probes and their dynamic behavior in cell plasma membranes as revealed by single-molecule imaging. Glycoconjugate Journal 2023, 40 (3) , 305-314. https://doi.org/10.1007/s10719-023-10116-9
    3. Hide-Nori Tanaka. Development of a Synthetic Strategy for Gangliosides Using the Unique Chemical Structure of Sialic Acid. Trends in Glycoscience and Glycotechnology 2023, 35 (205) , E34-E37. https://doi.org/10.4052/tigg.2312.2E
    4. Hide-Nori Tanaka. Development of a Synthetic Strategy for Gangliosides Using the Unique Chemical Structure of Sialic Acid. Trends in Glycoscience and Glycotechnology 2023, 35 (205) , J34-J37. https://doi.org/10.4052/tigg.2312.2J
    5. Eriko Yamaguchi, Naoko Komura, Hide-Nori Tanaka, Akihiro Imamura, Hideharu Ishida, Sophie Groux-Degroote, Martina Mühlenhoff, Kenichi G. N. Suzuki, Hiromune Ando. Fluorescent GD2 analog for single-molecule imaging. Glycoconjugate Journal 2023, 40 (2) , 247-257. https://doi.org/10.1007/s10719-023-10102-1
    6. Yuki Suganuma, Akihiro Imamura, Hiromune Ando, Makoto Kiso, Hiromu Takematsu, Takeshi Tsubata, Hideharu Ishida. Improved synthesis of CD22-binding sialosides and its application for further development of potent CD22 inhibitors. Glycoconjugate Journal 2023, 40 (2) , 225-246. https://doi.org/10.1007/s10719-023-10098-8
    7. Kenichi G.N. Suzuki, Akihiro Kusumi. Refinement of Singer-Nicolson fluid-mosaic model by microscopy imaging: Lipid rafts and actin-induced membrane compartmentalization. Biochimica et Biophysica Acta (BBA) - Biomembranes 2023, 1865 (2) , 184093. https://doi.org/10.1016/j.bbamem.2022.184093
    8. Kenichi G. N. Suzuki. Single-Molecule Imaging of Ganglioside Probes in Living Cell Plasma Membranes. 2023, 215-227. https://doi.org/10.1007/978-1-0716-2910-9_17
    9. Maina Takahashi, Naoko Komura, Yukako Yoshida, Eriko Yamaguchi, Ami Hasegawa, Hide-Nori Tanaka, Akihiro Imamura, Hideharu Ishida, Kenichi G. N. Suzuki, Hiromune Ando. Development of lacto-series ganglioside fluorescent probe using late-stage sialylation and behavior analysis with single-molecule imaging. RSC Chemical Biology 2022, 3 (7) , 868-885. https://doi.org/10.1039/D2CB00083K
    10. Erino Araki, Masaya Hane, Rina Hatanaka, Ryota Kimura, Kana Tsuda, Miku Konishi, Naoko Komura, Hiromune Ando, Ken Kitajima, Chihiro Sato. Analysis of biochemical features of ST8 α-N-acetyl-neuraminide α2,8-sialyltransferase (St8sia) 5 isoforms. Glycoconjugate Journal 2022, 39 (2) , 291-302. https://doi.org/10.1007/s10719-021-10034-8
    11. Hiromune Ando, Naoko Komura, Hide-Nori Tanaka, Akihiro Imamura, Hideharu Ishida. Chemical synthesis of sialoglyco-architectures. 2022, 31-56. https://doi.org/10.1016/bs.accb.2022.09.003
    12. Amol M. Vibhute, Naoko Komura, Hide‐Nori Tanaka, Akihiro Imamura, Hiromune Ando. Advanced Chemical Methods for Stereoselective Sialylation and Their Applications in Sialoglycan Syntheses. The Chemical Record 2021, 21 (11) , 3194-3223. https://doi.org/10.1002/tcr.202100080
    13. Naoko KOMURA. Syntheses of Sialic Acid-Containing Glycans and Their Biological Significances: Applications to the Study of Lipid Rafts. KAGAKU TO SEIBUTSU 2021, 59 (9) , 418-425. https://doi.org/10.1271/kagakutoseibutsu.59.418