Synthesis and cytotoxicity assay of four ganglioside GM3 analogues

• We reported the preparation of GM3 analogues based on a concise protocol.
• The key step here is a highly regioselective and stereoselective α-sialylation.
• Two glucose-containing GM3 analogues exhibited good antiproliferative activity.
• Selected compounds showed better cytotoxicity against cancer cell than normal cell.
• This work will facilitate construction of various GM3 analogues.

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.

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