Aminoalkylindole binding in rat cerebellum: selective displacement by natural and synthetic cannabinoids

J Pharmacol Exp Ther. 1993 Mar;264(3):1352-63.

Abstract

A binding assay for WIN 55212-2, an aminoalkylindole (AAI) with antinociceptive activity in rodents, is described. [3H]WIN 55212-2 bound to rat cerebellar membranes with a Kd of 2 nM and a maximum binding of 1.2 pmol/mg of protein. Specific binding in this filtration assay was greater than 90%, saturable, reversible, stereospecific, pH sensitive and heat labile. Binding was decreased by Na+, K+, Li+ and nonhydrolyzable analogs of GTP and increased by Mg++ and Ca++. The density of specific binding sites varied throughout the central nervous system with the highest found in the cerebellum, hippocampus and striatum and the lowest in the medulla/pons and spinal cord. The binding affinities of other AAIs for the WIN 55212-2 binding site correlated with their potencies for inhibiting neuronally stimulated contractions in the isolated mouse vas deferens. Of more than 60 compounds representing recognized neurotransmitter systems, only cannabinoids effectively inhibited binding. The effect of cannabinoids on AAI binding was consistent with competitive inhibition and suggests that AAI activity may be mediated in whole or in part by interaction with cannabinoid receptors. AAIs appear to represent a structurally novel class of compounds with which to study cannabinoid receptors.

MeSH terms

  • Analgesics / metabolism*
  • Animals
  • Benzoxazines
  • Binding, Competitive
  • Cannabinoids / pharmacology*
  • Cerebellum / metabolism*
  • Cyclohexanols / metabolism
  • Guanosine Triphosphate / pharmacology
  • In Vitro Techniques
  • Kinetics
  • Magnesium / pharmacology
  • Male
  • Morpholines / metabolism*
  • Naphthalenes / metabolism*
  • Rats
  • Rats, Sprague-Dawley
  • Receptors, Cannabinoid
  • Receptors, Drug / drug effects
  • Stereoisomerism

Substances

  • Analgesics
  • Benzoxazines
  • Cannabinoids
  • Cyclohexanols
  • Morpholines
  • Naphthalenes
  • Receptors, Cannabinoid
  • Receptors, Drug
  • (3R)-((2,3-dihydro-5-methyl-3-((4-morpholinyl)methyl)pyrrolo-(1,2,3-de)-1,4-benzoxazin-6-yl)(1-naphthalenyl))methanone
  • 3-(2-hydroxy-4-(1,1-dimethylheptyl)phenyl)-4-(3-hydroxypropyl)cyclohexanol
  • Guanosine Triphosphate
  • Magnesium