Synthesis and cytotoxicity assay of four ganglioside GM3 analogues

被引：6
作者：
Qu, Huanhuan [1 ,2 ]
Liu, Jian-Miao [3 ]
Wdzieczak-Bakala, Joanna [3 ]
Lu, Dan [1 ]
He, Xianran [4 ]
Sun, Wenji [5 ]
Sollogoub, Matthieu [1 ]
Zhang, Yongmin [1 ,4 ,5 ]
机构：
[1] Univ Paris 06, Sorbonne Univ, LabEx Michem, IPCM,CNRS,UMR 8232, F-75005 Paris, France
[2] Chinese Acad Sci, Shanghai Inst Mat Med, Glycochem & Glycobiol Lab, Shanghai 201203, Peoples R China
[3] CNRS, UPR 2301, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France
[4] Jianghan Univ, Wuhan Econ & Technol Dev Zone, Inst Interdisciplinary Res, Wuhan 430056, Peoples R China
[5] NW Univ Xian, Biomed Key Lab Shaanxi Prov, Xian 710069, Peoples R China
来源：
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY | 2014年 / 75卷
关键词：
Synthesis; Sialylation; Cytotoxicity; Cancer; Ganglioside GM3; Sialic acid; N-ACETYLNEURAMINIC ACID; MELANOMA B16 CELLS; GROWTH-FACTOR RECEPTOR; NEURAMINIC-ACID; STEREOSELECTIVE SYNTHESIS; SIALIC ACIDS; 3-O-BENZOYL AZIDOSPHINGOSINE; GLYCOSYNAPTIC MICRODOMAINS; MEDIATED MODULATION; IODINE MONOBROMIDE;
D O I：
10.1016/j.ejmech.2014.01.054
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
A concise and efficient synthetic route for preparation of four ganglioside GM3 analogues was described. The key step is a highly regioselective and stereoselective alpha-sialylation from a suitably protected glycoside acceptor with a sialyl xanthate to provide the sialo-oligosaccharide in good yield. The cytotoxic properties of the synthetic gangliosides were evaluated against normal human keratinocytes and human HCT116 and 1(562 cancer cells. Two of them exhibited good antiproliferative activity and displayed a better cytotoxicity against cancer cell than HaCaT normal cell. (C) 2014 Elsevier Masson SAS. All rights reserved.
引用
收藏
页码：247 / 257
页数：11
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