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用于单分子成像的荧光GD2类似物。

Fluorescent GD2 analog for single-molecule imaging.

作者信息

Yamaguchi Eriko, Komura Naoko, Tanaka Hide-Nori, Imamura Akihiro, Ishida Hideharu, Groux-Degroote Sophie, Mühlenhoff Martina, Suzuki Kenichi G N, Ando Hiromune

机构信息

Institute for Glyco-core Research (iGCORE), Gifu University, 1-1 Yanagido, 501-1193, Gifu, Japan.

Department of Applied Bioorganic Chemistry, Gifu University, 1-1 Yanagido, 501-1193, Gifu, Japan.

出版信息

Glycoconj J. 2023 Apr;40(2):247-257. doi: 10.1007/s10719-023-10102-1. Epub 2023 Jan 26.

DOI:10.1007/s10719-023-10102-1
PMID:36701103
Abstract

Ganglioside GD2 is associated with the proliferation and migration of breast cancer cells. However, the precise role of GD2 is unclear because its tendency to form dynamic and transient domains in cell plasma membranes (PMs), called lipid rafts, makes it difficult to observe. Previously, we developed fluorescent analogs of gangliosides (e.g., GM3 and GM1), which enabled the observation of lipid raft formation for the first time using single-molecule imaging. In this report, we describe the first chemical synthesis of a fluorescent ganglioside, GD2. A biophysical analysis of the synthesized analog revealed its raft-philic character, suggesting its potential to aid single-molecule imaging-based investigations into raft-associated interactions.

摘要

神经节苷脂GD2与乳腺癌细胞的增殖和迁移有关。然而,GD2的确切作用尚不清楚,因为它倾向于在细胞质膜(PMs)中形成动态和瞬时结构域,即脂筏,这使得观察变得困难。此前,我们开发了神经节苷脂的荧光类似物(如GM3和GM1),首次使用单分子成像观察到了脂筏的形成。在本报告中,我们描述了荧光神经节苷脂GD2的首次化学合成。对合成类似物的生物物理分析揭示了其亲脂筏特性,表明它有潜力辅助基于单分子成像的脂筏相关相互作用研究。

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Fluorescent GD2 analog for single-molecule imaging.用于单分子成像的荧光GD2类似物。
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2
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引用本文的文献

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Recently developed glycosphingolipid probes and their dynamic behavior in cell plasma membranes as revealed by single-molecule imaging.最近开发的糖脂探针及其在细胞质膜中的单分子成像揭示的动态行为。
Glycoconj J. 2023 Jun;40(3):305-314. doi: 10.1007/s10719-023-10116-9. Epub 2023 May 3.

本文引用的文献

1
Development of lacto-series ganglioside fluorescent probe using late-stage sialylation and behavior analysis with single-molecule imaging.利用晚期唾液酸化开发乳糖系列神经节苷脂荧光探针及单分子成像行为分析
RSC Chem Biol. 2022 May 31;3(7):868-885. doi: 10.1039/d2cb00083k. eCollection 2022 Jul 6.
2
Development of Fluorescent Ganglioside GD3 and GQ1b Analogs for Elucidation of Raft-Associated Interactions.荧光神经节苷脂 GD3 和 GQ1b 类似物的开发用于阐明筏相关相互作用。
J Org Chem. 2020 Dec 18;85(24):15998-16013. doi: 10.1021/acs.joc.0c01493. Epub 2020 Sep 30.
3
Disialoganglioside GD2 Expression in Solid Tumors and Role as a Target for Cancer Therapy.
双唾液酸神经节苷脂GD2在实体瘤中的表达及其作为癌症治疗靶点的作用。
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Development of Fluorescently Labeled SSEA-3, SSEA-4, and Globo-H Glycosphingolipids for Elucidating Molecular Interactions in the Cell Membrane.荧光标记的 SSEA-3、SSEA-4 和 Globo-H 糖脂的开发用于阐明细胞膜中的分子相互作用。
Int J Mol Sci. 2019 Dec 7;20(24):6187. doi: 10.3390/ijms20246187.
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p- tert-Butyl Groups Improve the Utility of Aromatic Protecting Groups in Carbohydrate Synthesis.p-叔丁基改善了芳香族保护基团在碳水化合物合成中的实用性。
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Raft-based interactions of gangliosides with a GPI-anchored receptor.神经节苷脂与糖基磷脂酰肌醇锚定受体的筏基相互作用。
Nat Chem Biol. 2016 Jun;12(6):402-10. doi: 10.1038/nchembio.2059. Epub 2016 Apr 4.
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The sweet spot: defining virus-sialic acid interactions.甜蜜点:定义病毒-唾液酸相互作用。
Nat Rev Microbiol. 2014 Nov;12(11):739-49. doi: 10.1038/nrmicro3346. Epub 2014 Sep 29.
8
Transient GPI-anchored protein homodimers are units for raft organization and function.瞬时糖基磷脂酰肌醇锚定蛋白同源二聚体是筏结构和功能的单位。
Nat Chem Biol. 2012 Sep;8(9):774-83. doi: 10.1038/nchembio.1028. Epub 2012 Jul 22.
9
Ganglioside GD2 identifies breast cancer stem cells and promotes tumorigenesis.神经节苷脂 GD2 鉴定乳腺癌干细胞并促进肿瘤发生。
J Clin Invest. 2012 Jun;122(6):2066-78. doi: 10.1172/JCI59735. Epub 2012 May 15.
10
Efficiently synthesizing lacto-ganglio-series gangliosides by using a glucosyl ceramide cassette approach: the total synthesis of ganglioside X2.通过使用葡萄糖神经酰胺盒式方法高效合成乳酰神经节苷脂系列神经节苷脂:神经节苷脂 X2 的全合成。
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