Selective effects of [D-Ser2(O-t-butyl),Leu5]enkephalyl-Thr6 and [D-Ser2(O-t-butyl),Leu5]enkephalyl-Thr6 (O-t-butyl), two new enkephalin analogues, on neurotransmitter release and adenylate cyclase in rat brain slices

Eur J Pharmacol. 1989 Nov 7;170(3):137-43. doi: 10.1016/0014-2999(89)90534-7.

Abstract

The selectivity and potency of two new enkephalin-derived delta-opioid receptor agonists, DSTBULET ([D-Ser2(O-t-butyl),Leu5]enkephalyl-Thr6) and BUBU ([D-Ser2(O-t-butyl),Leu5]enkephalyl-Thr6(O-t-butyl] were determined with functional tests in vitro of mu-, delta- and kappa-opioid receptor activation in the rat brain. Both peptides concentration dependently (1 nM-1 microM) inhibited the release of radiolabeled acetylcholine (ACh) from striatal slices (pD2 7.6-7.9), an effect exclusively mediated by delta-opioid receptor activation. Fentanyl isothiocyanate (FIT), an irreversible delta-antagonist, completely blocked the inhibitory effects of DSTBULET and BUBU. Up to a concentration of 1 microM, the peptides did not affect striatal [3H]dopamine (DA) release nor cortical [3H]noradrenaline (NA) release, processes which are known to be inhibited by opioids activating kappa and mu-receptors, respectively. Furthermore, both DSTBULET and BUBU caused a strong inhibition (pD2 8.2-8.3) of D-1 dopamine receptor-stimulated cyclic AMP efflux from striatal slices, an effect known to be mediated by mu- and/or delta-opioid receptor activation. However, the peptides were without effect when D-1 and D-2 dopamine receptors were stimulated simultaneously, a situation in which only mu-agonists are able to inhibit the resulting cAMP efflux. In conclusion, DSTBULET and BUBU appear to display a high selectivity and potency toward functional delta-opioid receptors in the brain.

MeSH terms

  • Adenylyl Cyclases / metabolism*
  • Alkylating Agents / pharmacology
  • Animals
  • Brain / drug effects
  • Brain / enzymology*
  • Brain / physiology
  • Corpus Striatum / drug effects
  • Corpus Striatum / metabolism
  • Cyclic AMP / metabolism
  • Dopamine / metabolism
  • Electric Stimulation
  • Enkephalins / pharmacology*
  • Fentanyl / analogs & derivatives
  • Fentanyl / pharmacology
  • Isothiocyanates*
  • Male
  • Neurotransmitter Agents / metabolism*
  • Oligopeptides / pharmacology*
  • Rats
  • Rats, Inbred Strains

Substances

  • Alkylating Agents
  • Enkephalins
  • Isothiocyanates
  • Neurotransmitter Agents
  • Oligopeptides
  • tyrosyl-seryl(O-tert-butyl)-glycyl-phenylalanyl-leucyl-threonine
  • tyrosyl-seryl(O-t-butyl)-glycyl-phenylalanyl-leucyl-threonine(O-t-butyl)
  • fentanyl isothiocyanate
  • Cyclic AMP
  • Adenylyl Cyclases
  • Fentanyl
  • Dopamine