title: Synthesis and cytotoxicity assay of four ganglioside GM3 analogues.
abstract: 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.
authors.affiliation: 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.
authors.forename: Huanhuan
authors.initials: H
authors.lastname: Qu
authors.affiliation: Institut de Chimie des Substances Naturelles, UPR 2301, CNRS, avenue de la Terrasse, F-91198 Gif sur Yvette, France.
authors.forename: Jian-Miao
authors.initials: JM
authors.lastname: Liu
authors.affiliation: Institut de Chimie des Substances Naturelles, UPR 2301, CNRS, avenue de la Terrasse, F-91198 Gif sur Yvette, France.
authors.forename: Joanna
authors.initials: J
authors.lastname: Wdzieczak-Bakala
authors.affiliation: Sorbonne Universités, UPMC Univ Paris 06, LabEx Michem, CNRS, UMR 8232, IPCM, F-75005 Paris, France.
authors.forename: Dan
authors.initials: D
authors.lastname: Lu
authors.affiliation: Institute for Interdisciplinary Research, Jianghan University, Wuhan Economic and Technological Development Zone, Wuhan 430056, China.
authors.forename: Xianran
authors.initials: X
authors.lastname: He
authors.affiliation: Biomedicine Key Laboratory of Shaanxi Province, Northwest University, Xi'an 710069, China.
authors.forename: Wenji
authors.initials: W
authors.lastname: Sun
authors.affiliation: Sorbonne Universités, UPMC Univ Paris 06, LabEx Michem, CNRS, UMR 8232, IPCM, F-75005 Paris, France.
authors.forename: Matthieu
authors.initials: M
authors.lastname: Sollogoub
authors.affiliation: Sorbonne Universités, UPMC Univ Paris 06, LabEx Michem, CNRS, UMR 8232, IPCM, F-75005 Paris, France; Institute for Interdisciplinary Research, Jianghan University, Wuhan Economic and Technological Development Zone, Wuhan 430056, China; Biomedicine Key Laboratory of Shaanxi Province, Northwest University, Xi'an 710069, China. Electronic address: yongmin.zhang@upmc.fr.
authors.forename: Yongmin
authors.initials: Y
authors.lastname: Zhang
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D002460:Cell Line; D045744:Cell Line, Tumor; D003603:Cytotoxins / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D005679:G(M3) Ganglioside / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology*; D006801:Humans; D015603:Keratinocytes / Q000187:drug effects; D019158:N-Acetylneuraminic Acid / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D009369:Neoplasms / Q000188:drug therapy / Q000473:pathology
chemical_list: D000970:Antineoplastic Agents; D003603:Cytotoxins; D005679:G(M3) Ganglioside; D019158:N-Acetylneuraminic Acid
keywords: Cancer; Cytotoxicity; Ganglioside GM3; Sialic acid; Sialylation; Synthesis