Synthesis, conformation and opioid activity of deltorphins

Biochem Biophys Res Commun. 1995 Feb 6;207(1):99-104. doi: 10.1006/bbrc.1995.1158.

Abstract

A series of deltorphin analogues was prepared by solid-phase peptide synthesis. Their opioid activity was evaluated in rat opiatic assay and their conformation was determined by two-dimension Nuclear Magnetic Resonance Spectroscopy. The analogues containing D-alanine acid at position 2 were much more potent in the assay than their corresponding isomers containing L-alanine acid at this position. The conformational analysis on NMR study in DMSO showed that C-terminal tetrapeptides of both deltorphin II and its L-alanine analog might form a 3(10) helix, which confirms that the substitution of D-amino acid at position 2 decreased the opioid activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Analgesics / pharmacology*
  • Animals
  • Chromatography, High Pressure Liquid
  • Dimethyl Sulfoxide
  • Indicators and Reagents
  • Magnetic Resonance Spectroscopy / methods
  • Male
  • Models, Molecular
  • Oligopeptides / chemical synthesis
  • Oligopeptides / chemistry*
  • Oligopeptides / pharmacology
  • Pain / physiopathology
  • Protein Conformation*
  • Rats
  • Rats, Wistar
  • Spectrometry, Mass, Fast Atom Bombardment
  • Structure-Activity Relationship

Substances

  • Analgesics
  • Indicators and Reagents
  • Oligopeptides
  • deltorphin
  • Dimethyl Sulfoxide