Synthesis and cytotoxicity assay of four ganglioside GM3 analogues

Eur J Med Chem. 2014 Mar 21:75:247-57. doi: 10.1016/j.ejmech.2014.01.054. Epub 2014 Jan 28.

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.

Keywords: Cancer; Cytotoxicity; Ganglioside GM3; Sialic acid; Sialylation; Synthesis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / pharmacology*
  • Cell Line
  • Cell Line, Tumor
  • Cytotoxins / chemical synthesis
  • Cytotoxins / chemistry
  • Cytotoxins / pharmacology
  • G(M3) Ganglioside / analogs & derivatives*
  • G(M3) Ganglioside / chemical synthesis
  • G(M3) Ganglioside / pharmacology*
  • Humans
  • Keratinocytes / drug effects
  • N-Acetylneuraminic Acid / chemical synthesis
  • N-Acetylneuraminic Acid / chemistry*
  • N-Acetylneuraminic Acid / pharmacology*
  • Neoplasms / drug therapy
  • Neoplasms / pathology

Substances

  • Antineoplastic Agents
  • Cytotoxins
  • G(M3) Ganglioside
  • N-Acetylneuraminic Acid