Opioid antagonist properties of the highly delta-receptor-selective BOC-Tyr-Pro-Gly-Phe-Leu-Thr (OtBu) peptide and of its Phe1 and Mel1 analogues

Arch Int Pharmacodyn Ther. 1995 Nov-Dec;330(3):361-9.

Abstract

BOC-Tyr-Pro-Gly-Phe-Leu-Thr(OtBu) is a potent, highly delta-opioid receptor-selective competitive antagonist, the Ke values in the mouse vas deferens in vitro assay against [D-Ala2, D-Leu5]-enkephalin [D-Pen2, D-Pen5]enkephalin and deltorphin-II being 39.5, 38.7 and 27.3 nM, respectively, whereas those against [D-Ala2, MePhe4-Gly5-ol]enkephalin (DAMGO) and ethylketocyclazocine in the guinea-pig ileum are 368,000 and > 200,000 nM, giving a higher than 9000-fold delta- vs mu- and a higher than 5000-fold delta- vs kappa-selectivity ratio. The Ki values against various labeled delta-ligands in the rat brain receptor binding assay were in the 300-1000 nM range, whereas the Ki against [3H]-DAMGO was higher than 30,000 nM. The striking discrepancies between bioassay and receptor binding data show another aspect of already recognized differences of mouse vas deferens and rat brain delta-receptors. With the aim of producing a delta-selective affinity ligand, we synthesized the BOC-Mel1 derivative; however, there was a 175-fold loss of delta-receptor affinity in the bioassay and no indication of an irreversible interaction, but a delta-agonist effect appeared in spite of nonprotonated nitrogen. The corresponding BOC-Phe1 derivative had a 10 times higher affinity and, apparently, no agonist activity.

MeSH terms

  • Analgesics / metabolism
  • Analgesics / pharmacology
  • Animals
  • Binding, Competitive
  • Enkephalin, Ala(2)-MePhe(4)-Gly(5)-
  • Enkephalin, D-Penicillamine (2,5)-
  • Enkephalin, Leucine-2-Alanine / metabolism
  • Enkephalin, Leucine-2-Alanine / pharmacology
  • Enkephalins / metabolism
  • Enkephalins / pharmacology
  • Lethal Dose 50
  • Male
  • Mice
  • Oligopeptides / metabolism
  • Oligopeptides / pharmacology*
  • Radioligand Assay
  • Rats
  • Receptors, Opioid, delta / antagonists & inhibitors*
  • Vas Deferens / drug effects*
  • Vas Deferens / metabolism

Substances

  • Analgesics
  • Enkephalins
  • Oligopeptides
  • Receptors, Opioid, delta
  • Enkephalin, Ala(2)-MePhe(4)-Gly(5)-
  • deltorphin II, Ala(2)-
  • tert-butyloxycarbonyl-tyrosyl-prolyl-glycyl-phenylalanyl-leucyl-(O-tert-butyl)threonine
  • Enkephalin, Leucine-2-Alanine
  • Enkephalin, D-Penicillamine (2,5)-