Synthesis, biological activity and conformational studies of geometrically restricted tripeptide analogues of the chemoattractant HCO-Met-Leu-Phe-OMe

Farmaco. 1997 Jun-Jul;52(6-7):439-44.

Abstract

The formyl tripeptides containing 2-azetidinecarboxylic acid 2, 2-piperidinecarboxylic acid 3 and norvaline 4 in position 2 were synthesized and their biological activity was evaluated. The conformation of peptides was studied by CD and FT-IR techniques. While 2 and 3 do not show either chemotactic activity or superoxide production, 4 retains both activities.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cell Movement
  • Chemotactic Factors / chemistry*
  • Chemotactic Factors / pharmacology
  • Humans
  • N-Formylmethionine Leucyl-Phenylalanine / analogs & derivatives*
  • N-Formylmethionine Leucyl-Phenylalanine / chemistry
  • N-Formylmethionine Leucyl-Phenylalanine / pharmacology
  • Neutrophils / drug effects*
  • Neutrophils / metabolism
  • Neutrophils / physiology
  • Oligopeptides / chemistry*
  • Oligopeptides / pharmacology
  • Protein Conformation
  • Solutions
  • Superoxides / metabolism

Substances

  • Chemotactic Factors
  • Oligopeptides
  • Solutions
  • Superoxides
  • N-Formylmethionine Leucyl-Phenylalanine
  • formylmethionyl-leucyl-phenylalanine methyl ester