D-piece modifications of the hemiasterlin analog HTI-286 produce potent tubulin inhibitors

Bioorg Med Chem Lett. 2004 Aug 16;14(16):4353-8. doi: 10.1016/j.bmcl.2004.05.005.

Abstract

Modifications of the D-piece carboxylic acid group of the hemiasterlin analog HTI-286 gave tubulin inhibitors which were potent cytotoxic agents in taxol resistant cell lines expressing P-glycoprotein. Amides derived from proline had potency comparable to HTI-286. Reduction of the carboxylic acid to ketones and alcohols or its conversion to acidic heterocycles also gave potent analogs. Synthetic modifications of the carboxylic acid could be carried out selectively using a wide range of synthetic reagents. Proline analog 3 was found to be effective in a human xenograft model in athymic mice.

MeSH terms

  • Animals
  • Humans
  • Mice
  • Mice, Nude
  • Oligopeptides / chemistry*
  • Oligopeptides / pharmacology
  • Transplantation, Heterologous
  • Tubulin Modulators*

Substances

  • HTI-286
  • Oligopeptides
  • Tubulin Modulators