Opioid receptor selectivity reversal in deltorphin tetrapeptide analogues

Biochem Biophys Res Commun. 1991 Jul 15;178(1):110-5. doi: 10.1016/0006-291x(91)91786-c.

Abstract

Deltorphin N-terminal tetrapeptides [DEL A: H-Tyr-D-Met-Phe-His-R, where R = -NH2, -NH-NH2, -OCH3, -OH, -NH-NH-CO-R' (R' = -CH3 or adamantane); DEL C: H-Tyr-D-Ala-Asp-R (R = -OH, -NHCH3)], were used in a receptor binding assay with [3H]DADLE and [3H]DPDPE for delta sites, and [3H]DAGO for mu sites; tetrapeptide Ki delta values were similar with either [3H]-delta ligand. DEL A tetrapeptides C-terminally substituted with -NH2, -NH-NH2, -OCH3, and -OH had 10 to greater than 1,000-fold decreased Ki delta values, while Ki mu increased 5 to 100-fold to yield mu selectivity. C-Terminal substitution with -NH-NH2 and -OCH3 conferred highest mu selectivities; adamantyl and acetyl hydrazide derivatives were non-selective. DEL-(1-4)-OH peptides had decreased delta and mu affinities: DEL A-[Asp4]-(1-4)-OH and DEL C-(1-4)-OH had low affinities (greater than 1 microM), however, the Ki delta of the former was 5-fold greater than the latter, and the Ki mu was less by 15-fold. The data suggest that the "message" domain of DEL exhibits receptor selectivity different from that of the heptapeptide.

MeSH terms

  • Animals
  • Brain / metabolism
  • Enkephalin, Ala(2)-MePhe(4)-Gly(5)-
  • Enkephalin, D-Penicillamine (2,5)-
  • Enkephalin, Leucine-2-Alanine / metabolism
  • Enkephalins / metabolism
  • Kinetics
  • Oligopeptides / pharmacology*
  • Rats
  • Receptors, Opioid / drug effects
  • Receptors, Opioid / metabolism*
  • Receptors, Opioid, delta
  • Receptors, Opioid, mu
  • Structure-Activity Relationship
  • Synaptosomes / metabolism*

Substances

  • Enkephalins
  • Oligopeptides
  • Receptors, Opioid
  • Receptors, Opioid, delta
  • Receptors, Opioid, mu
  • Enkephalin, Ala(2)-MePhe(4)-Gly(5)-
  • deltorphin
  • Enkephalin, Leucine-2-Alanine
  • Enkephalin, D-Penicillamine (2,5)-