Synthesis and structure-activity relationships of deltorphin analogues

J Med Chem. 1991 May;34(5):1656-61. doi: 10.1021/jm00109a019.


In order to study the structure-activity relationships of natural opioid deltorphins (H-Tyr-D-Met-Phe-His-Leu-Met-Asp-NH2 and H-Tyr-D-Ala-Phe-Asp [or Glu]-Val-Val-Gly-NH2), 15 analogues were synthesized by the solution method. Their activities were determined in binding studies based on displacement of mu- and delta-receptor selective radiolabels from rat brain membranes and in two bioassays, using guinea pig ileum and mouse vas deferens. The obtained data indicate that the high delta-selectivity of deltorphins can be due to the constitution/conformation of the C-terminal part and, at least in part, to preselection by charge.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acid Sequence
  • Animals
  • Binding, Competitive / drug effects
  • Chemical Phenomena
  • Chemistry
  • Guinea Pigs
  • Male
  • Mice
  • Molecular Sequence Data
  • Muscle, Smooth / drug effects
  • Oligopeptides / chemical synthesis*
  • Oligopeptides / metabolism
  • Oligopeptides / pharmacology
  • Rats
  • Rats, Inbred Strains
  • Receptors, Opioid / drug effects
  • Structure-Activity Relationship


  • Oligopeptides
  • Receptors, Opioid
  • deltorphin
  • deltorphin I, Ala(2)-
  • deltorphin II, Ala(2)-