Synthesis of novel 6-triazologlycolipids via click chemistry and their preliminary cytotoxicity assessments

Mol Divers. 2011 Nov;15(4):889-900. doi: 10.1007/s11030-011-9318-1. Epub 2011 Jun 5.

Abstract

Series of novel 6-triazole-linked galacto- or glucolipids were efficiently synthesized from O-benzylated sugar azides and various lipid alkynes via Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition (click chemistry) followed by hydrogenolysis with PdCl(2)/H(2). Subsequent MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide) assay toward a panel of human cancer cell lines revealed that these triazologlycolipids possess low-to-modest toxicity on A549 (lung), MCF-7 (breast), HeLa (cervix), and HepG2 (liver). Furthermore, both the carbon chain length at the lipid end and the epimeric identity of the glycosyl moiety were determined to impact their corresponding bioactivity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Cell Line, Tumor
  • Click Chemistry*
  • Drug Screening Assays, Antitumor
  • Glycolipids / chemical synthesis*
  • Glycolipids / chemistry
  • Glycolipids / pharmacology*
  • Glycosylation
  • Humans
  • Structure-Activity Relationship
  • Triazoles / chemistry*

Substances

  • Antineoplastic Agents
  • Glycolipids
  • Triazoles