Modified chemotactic peptides: synthesis and biological activity of HCO-Met-delta ZLeu-delta ZPhe-OMe

Farmaco. 1994 Nov;40(11):739-42.

Abstract

For-Met-delta ZLeu-delta ZPhe-OMe (3) has been synthesized as a new analogue of the prototypical chemotactic agent For-Met-Leu-Phe-OMe (fMLP-OMe). Compound 3 is characterized by presence of two consecutive alpha,beta-didehydro amino acid residues [delta ZLeu = (Z)-alpha,beta-didehydroleucine; delta ZPhe = (Z)-alpha,beta- didehydrophenylalanine] located at the central and C-terminal position, respectively. When tested on human neutrophils the N-formyltripeptide 3, although less active than the parent, is able to induce chemotaxis, superoxide anion production and lysozyme release. The activity of 3 has been compared to that of related fMLP-OMe analogues containing a single delta ZPhe residue located at the C-terminal position.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acid Sequence
  • Chemotactic Factors / chemical synthesis*
  • Chemotactic Factors / pharmacology
  • Humans
  • Molecular Sequence Data
  • N-Formylmethionine Leucyl-Phenylalanine / analogs & derivatives*
  • N-Formylmethionine Leucyl-Phenylalanine / chemical synthesis
  • N-Formylmethionine Leucyl-Phenylalanine / pharmacology
  • Structure-Activity Relationship

Substances

  • Chemotactic Factors
  • formyl-methionyl-delta(Z)-dehydroleucyl-phenylalanine methyl ester
  • N-Formylmethionine Leucyl-Phenylalanine
  • formylmethionyl-leucyl-phenylalanine methyl ester