Synthesis and activity of novel analogs of hemiasterlin as inhibitors of tubulin polymerization: modification of the A segment

Bioorg Med Chem Lett. 2004 Nov 1;14(21):5317-22. doi: 10.1016/j.bmcl.2004.08.024.

Abstract

Analogs of hemiasterlin (1) and HTI-286 (2), which contain various aromatic rings in the A segment, were synthesized as potential inhibitors of tubulin polymerization. The structure-activity relationships related to stereo- and regio-chemical effects of substituents on the aromatic ring in the A segment were studied. Analogs, which carry a meta-substituted phenyl ring in the A segment show comparable activity for inhibition of tubulin polymerization to 2, as well as in the cell proliferation assay using KB cells containing P-glycoprotein, compared to those of 1 and 2.

MeSH terms

  • Animals
  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology
  • Biopolymers
  • Cell Proliferation / drug effects
  • Humans
  • KB Cells
  • Melanoma, Experimental / drug therapy
  • Mice
  • Mice, Nude
  • Oligopeptides / chemical synthesis*
  • Oligopeptides / chemistry
  • Oligopeptides / pharmacology
  • Stereoisomerism
  • Structure-Activity Relationship
  • Tubulin / chemistry*
  • Tubulin Modulators*
  • Xenograft Model Antitumor Assays

Substances

  • Antineoplastic Agents
  • Biopolymers
  • HTI-286
  • Oligopeptides
  • Tubulin
  • Tubulin Modulators
  • hemiasterlin