Evidence for the rapid conversion of stephacidin B into the electrophilic monomer avrainvillamide in cell culture

J Am Chem Soc. 2007 Apr 25;129(16):4898-9. doi: 10.1021/ja0690971. Epub 2007 Mar 31.


We report that the dimeric alkaloid stephacidin B (1) and the monomeric alkaloid avrainvillamide (2) function equivalently within experimental error to inhibit the growth of four different cultured human cancer cell lines. We also show that the proportion of the monomer greatly outweighs that of the dimer in the medium of incubation, and that the half-life for the transformation of 1 to 2 is short relative to the half-life of cell division. Finally, using a monomer-based affinity reagent, we provide evidence that the monomer (2) interacts with intracellular thiol-containing proteins, likely by covalent modification.

Publication types

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

MeSH terms

  • Cell Proliferation / drug effects*
  • Cysteine / analysis
  • Humans
  • Indole Alkaloids / chemistry
  • Indole Alkaloids / metabolism*
  • Indole Alkaloids / pharmacology*
  • Indoles / chemistry
  • Indoles / metabolism*
  • Indoles / pharmacology*
  • Neoplasm Proteins / metabolism
  • Neoplasms / metabolism
  • Tumor Cells, Cultured


  • Indole Alkaloids
  • Indoles
  • Neoplasm Proteins
  • avrainvillamide
  • stephacidin B
  • Cysteine