STRUCTURE-ACTIVITY STUDIES ON SYNTHETIC ANALOGS (INDOLACTAMS) OF THE TUMOR PROMOTER TELEOCIDIN

  • 1 January 1984
    • journal article
    • research article
    • Vol. 75  (10) , 866-870
Abstract
Synthetic analogs (indolactams) related to the tumor promoter teleocidin were synthesized chemically. Of 4 indolactam-V analogs lacking the monoterpenoid moiety of native teleocidin, (-)-indolactam-V bound to the 12-O-tetradecanoylphorbol-13-acetate receptor in cell membranes and induced adhesion of HL-60 cells and ornithine decarboxylase activity in mouse skin, although its effects were weaker than those of teleocidin. (+)-Indolactam-V and 2 isomers of epi-indolactam-V showed no induction of ornithine decarboxylase. Apparently, the S,S configuration of native teleocidin at the isopropyl residue and the hydroxymethyl group is necessary for activity.