Alpha-peptide/beta-sulfonamidopeptide hybrids: analogs of the chemotactic agent for-Met-Leu-Phe-OMe

Bioorg Med Chem. 2006 Apr 15;14(8):2642-52. doi: 10.1016/j.bmc.2005.11.043. Epub 2005 Dec 13.

Abstract

In order to gain information on the activity shown by alpha-peptide/beta-sulfonamidopeptide hybrid analogs of the potent chemotactic agent fMLF-OMe, a structure-activity study is reported on N-Boc- and N-formyl tripeptide models containing an aminoalkanesulfonic acid as central residue. Directed migration (chemotaxis), superoxide anion production, and lysozyme release have been measured. The biochemical functions and the conformational properties of the new compounds are discussed and related to previously studied models containing beta-residues.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cells, Cultured
  • Chemotactic Factors / chemistry*
  • Chemotactic Factors / pharmacology*
  • Humans
  • Hydrogen Bonding
  • Magnetic Resonance Spectroscopy
  • Oligopeptides / chemistry*
  • Oligopeptides / pharmacology*
  • Spectrophotometry, Infrared
  • Structure-Activity Relationship
  • Sulfonamides / chemistry*
  • Sulfonamides / pharmacology*

Substances

  • Chemotactic Factors
  • Oligopeptides
  • Sulfonamides