Pharmacological and functional biochemical properties of D-Ala2-D-Nle5-enkephalin-Arg-Phe

Regul Pept. 2004 Oct 15;122(2):139-46. doi: 10.1016/j.regpep.2004.06.017.

Abstract

Tyr-D-Ala-Gly-Phe-D-Nle-Arg-Phe (DADN) a synthetic analogue of the endogenous Met-enkephalin-Arg-Phe (Tyr-Gly-Gly-Phe-Met-Arg-Phe; MERF), was investigated in radioligand binding assays, [(35)S]GTPgammaS stimulation experiments as well as in in vivo algesiometric tests. Binding properties of [(3)H]DADN were measured in crude membrane fractions of rat spinal cord tissues and in homogenates of Chinese hamster ovary (CHO) cells selectively expressing delta-, kappa-or micro-opioid receptors. The highest affinity for [(3)H]DADN binding was observed in membranes from CHO cells transfected with micro-opioid receptors confirming the micro-selectivity of the peptide. Unlabeled DADN was also investigated in functional biochemical experiments by measuring opioid receptor-mediated G-protein activation in rat brain membrane fractions. The peptide stimulated the activity of the regulatory G-proteins in a concentration dependent manner, and the stimulation was efficiently inhibited in the presence of micro-receptor specific antagonist ligands further supporting the selectivity profile of DADN. Intrathecally administered DADN produced a dose-related, naloxone-reversible antinociception in rat hot water tail-flick tests. Among the selective opioid antagonists tested, the delta-selective naltrindole (NTI) and the kappa-specific norbinaltorphimine (norBNI) showed only slight blocking effects compared with naloxone. The results obtained in the in vitro agonist-stimulated [(35)S]GTPgammaS binding assays are in good agreement with the opioid agonist effect seen in the in vivo pain test.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Binding, Competitive
  • CHO Cells
  • Cell Membrane / metabolism
  • Cricetinae
  • Enkephalins / chemistry*
  • Enkephalins / metabolism
  • Enkephalins / pharmacology*
  • Guanosine 5'-O-(3-Thiotriphosphate) / metabolism
  • Hot Temperature
  • Inhibitory Concentration 50
  • Rats
  • Rats, Wistar
  • Receptors, Opioid / metabolism
  • Spinal Cord / cytology
  • Spinal Cord / metabolism
  • Stress, Physiological / chemically induced
  • Stress, Physiological / physiopathology
  • Tail / drug effects
  • Tail / physiology
  • Time Factors
  • Water / pharmacology

Substances

  • D-Ala2-D-Nle5-enkephalin-Arg-Phe
  • Enkephalins
  • Receptors, Opioid
  • Water
  • Guanosine 5'-O-(3-Thiotriphosphate)