Cryptophycin affinity labels: synthesis and biological activity of a benzophenone analogue of cryptophycin-24

Bioorg Med Chem Lett. 2003 Feb 24;13(4):757-60. doi: 10.1016/s0960-894x(02)01023-5.

Abstract

An efficient synthesis of a C16 side chain benzophenone analogue of cryptophycin-24 using a crotylboration reaction and Heck coupling as key steps is described. In an in vitro tubulin assembly assay, the benzophenone analogue of the beta isomer (IC(50)=7.4 microM) is twice as active as cryptophycin-24 (IC(50)=15 microM).

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Affinity Labels
  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / pharmacology
  • Benzophenones / chemistry*
  • Cell Division / drug effects
  • Cell Line, Tumor
  • Depsipeptides*
  • Humans
  • Inhibitory Concentration 50
  • Peptides, Cyclic / chemical synthesis*
  • Peptides, Cyclic / pharmacology*
  • Structure-Activity Relationship
  • Tubulin / drug effects

Substances

  • Affinity Labels
  • Antineoplastic Agents
  • Benzophenones
  • Depsipeptides
  • Peptides, Cyclic
  • Tubulin
  • arenastatin A
  • cryptophycin