Separation of anti-angiogenic and cytotoxic activities of borrelidin by modification at the C17 side chain

Bioorg Med Chem Lett. 2006 Nov 15;16(22):5814-7. doi: 10.1016/j.bmcl.2006.08.073. Epub 2006 Sep 8.

Abstract

A set of novel borrelidin analogues have been prepared by precursor-directed biosynthesis. Structure-activity relationship analysis suggests that steric structural arrangement within the C17 side chain is important for differentiating cytotoxic and anti-angiogenic activities. A C17-cyclobutyl analogue 3 was found to have markedly increased selectivity for in vitro angiogenesis inhibition over cytotoxicity and is therefore potentially useful as an anticancer agent.

MeSH terms

  • Angiogenesis Inhibitors / chemical synthesis
  • Angiogenesis Inhibitors / pharmacology*
  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / pharmacology*
  • Cell Line, Tumor / drug effects
  • Cyclobutanes / chemistry*
  • Fatty Alcohols / chemical synthesis
  • Fatty Alcohols / pharmacology
  • Humans
  • Inhibitory Concentration 50
  • Structure-Activity Relationship

Substances

  • Angiogenesis Inhibitors
  • Antineoplastic Agents
  • Cyclobutanes
  • Fatty Alcohols
  • borrelidin