Cannabinoid CB2/CB1 selectivity. Receptor modeling and automated docking analysis

J Med Chem. 2006 Feb 9;49(3):984-94. doi: 10.1021/jm050875u.

Abstract

Three-dimensional models of the CB1 and CB2 cannabinoid receptors were constructed by means of a molecular modeling procedure, using the X-ray structure of bovine rhodopsin as the initial template, and taking into account the available site-directed mutagenesis data. The cannabinoid system was studied by means of docking techniques. An analysis of the interaction of WIN55212-2 with both receptors showed that CB2/CB1 selectivity is mainly determined by the interaction in the CB2 with the nonconserved residues S3.31 and F5.46, whose importance was suggested by site-directed mutagenesis data. We also carried out an automated docking of several ligands into the CB2 model, using the AUTODOCK 3.0 program; the good correlation obtained between the estimated free energy binding and the experimental binding data confirmed our binding hypothesis and the reliability of the model.

MeSH terms

  • Amino Acid Sequence
  • Animals
  • Arachidonic Acids / chemistry
  • Benzoxazines
  • Cattle
  • Endocannabinoids
  • Indoles / chemistry
  • Ligands
  • Models, Molecular*
  • Molecular Sequence Data
  • Morpholines / chemistry
  • Naphthalenes / chemistry
  • Naphthyridines / chemistry
  • Polyunsaturated Alkamides
  • Protein Conformation
  • Receptor, Cannabinoid, CB1 / chemistry*
  • Receptor, Cannabinoid, CB1 / genetics
  • Receptor, Cannabinoid, CB2 / chemistry*
  • Receptor, Cannabinoid, CB2 / genetics
  • Rhodopsin / chemistry
  • Structure-Activity Relationship
  • Thermodynamics

Substances

  • Arachidonic Acids
  • Benzoxazines
  • Endocannabinoids
  • Indoles
  • Ligands
  • Morpholines
  • Naphthalenes
  • Naphthyridines
  • Polyunsaturated Alkamides
  • Receptor, Cannabinoid, CB1
  • Receptor, Cannabinoid, CB2
  • (3R)-((2,3-dihydro-5-methyl-3-((4-morpholinyl)methyl)pyrrolo-(1,2,3-de)-1,4-benzoxazin-6-yl)(1-naphthalenyl))methanone
  • Rhodopsin
  • anandamide