Qu Huanhuan, Liu Jian-Miao, Wdzieczak-Bakala Joanna, Lu Dan, He Xianran, Sun Wenji, Sollogoub Matthieu, Zhang Yongmin
Sorbonne Universités, UPMC Univ Paris 06, LabEx Michem, CNRS, UMR 8232, IPCM, F-75005 Paris, France; Glycochemistry & Glycobiology Lab, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zu Chong Zhi Road, Pudong, Shanghai 201203, China.
Institut de Chimie des Substances Naturelles, UPR 2301, CNRS, avenue de la Terrasse, F-91198 Gif sur Yvette, France.
Eur J Med Chem. 2014 Mar 21;75:247-57. doi: 10.1016/j.ejmech.2014.01.054. Epub 2014 Jan 28.
A concise and efficient synthetic route for preparation of four ganglioside GM3 analogues was described. The key step is a highly regioselective and stereoselective α-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 K562 cancer cells. Two of them exhibited good antiproliferative activity and displayed a better cytotoxicity against cancer cell than HaCaT normal cell.
描述了一种简洁高效的合成路线，用于制备四种神经节苷脂GM3类似物。关键步骤是从适当保护的糖苷受体与唾液酸黄原酸盐进行高度区域选择性和立体选择性的α-唾液酸化反应，以高产率提供唾液酸化低聚糖。评估了合成神经节苷脂对正常人角质形成细胞以及人HCT116和K562癌细胞的细胞毒性。其中两种表现出良好的抗增殖活性，并且对癌细胞的细胞毒性比对HaCaT正常细胞更好。
