Synthesis and biological activity of pseudopeptides inhibitors of Ras farnesyl transferase containing unconventional amino acids

Farmaco. 1999 Nov-Dec;54(11-12):785-90. doi: 10.1016/s0014-827x(99)00104-4.

Abstract

A study was performed on the structure-activity relationships of a series of phenol derivatives, CVFM analogs, derived from the two most active compounds of a first series (1A and 1B) of inhibitors of Ras farnesyl transferase (FTase) that we have recently described. We report the synthesis and the activity of a second series of compounds in which the phenylalanine residue was replaced by unconventional aromatic and non-aromatic amino acids, with varying electronic, lipophilic, steric and conformational properties. The compounds showed to be significantly less active than reference compounds against FT, with the only exception of derivative 3A (IC50 = 3 microM), which is slightly more active than 1A but not 1B. Subsequently we tested the effects of compounds 1A, 1B and 3A, 3B on the anchorage-dependent growth of two epithelial cell lines of rats, FRTL-5 and the same line v-Ha-ras transformed. Compound 3A derived from lead compound 1A, showed an appreciable selectivity against transformed cells. In contrast, compounds derived from derivative 1B had only a modest cellular activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkyl and Aryl Transferases / antagonists & inhibitors*
  • Amino Acids / analysis*
  • Animals
  • Brain / enzymology
  • Cattle
  • Cell Line
  • Cell Line, Transformed
  • Cell Survival / drug effects
  • Enzyme Inhibitors / chemical synthesis*
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology*
  • Peptides / chemical synthesis*
  • Peptides / chemistry
  • Peptides / pharmacology*
  • Rats

Substances

  • Amino Acids
  • Enzyme Inhibitors
  • Peptides
  • Alkyl and Aryl Transferases
  • p21(ras) farnesyl-protein transferase