title: Enantiomeric resolution of a novel chiral cannabinoid receptor ligand.
abstract: The enantiomeric resolution of a racemic novel cannabinoid receptor ligand conformationally restricted at the southern aliphatic chain was accomplished using a ChiralPak AD column. Both enantiomers were tested for their competitive binding to the rat brain CB1, mouse spleen CB2 and human CB2 receptors. The levorotatory isomer showed exceptionally high affinity for the CB1 receptor with a seven-fold selectivity over CB2.
authors.affiliation: Department of Pharmaceutical Sciences and the Center for Drug Discovery, University of Connecticut, 372 Fairfield Road, Storrs, CT 06269, USA.
authors.forename: Ganesh A
authors.initials: GA
authors.lastname: Thakur
authors.forename: Sonya L
authors.initials: SL
authors.lastname: Palmer
authors.forename: Paul E
authors.initials: PE
authors.lastname: Harrington
authors.forename: Ioanna A
authors.initials: IA
authors.lastname: Stergiades
authors.forename: Marcus A
authors.initials: MA
authors.lastname: Tius
authors.forename: Alexandros
authors.initials: A
authors.lastname: Makriyannis
mesh_terms: D000688:Amylose / Q000031:analogs & derivatives*; D000818:Animals; D002186:Cannabinoids / Q000032:analysis* / Q000737:chemistry / Q000145:classification / Q000378:metabolism*; D002219:Carbamates; D002851:Chromatography, High Pressure Liquid / Q000295:instrumentation / Q000379:methods*; D006801:Humans; D007668:Kidney / Q000196:embryology / Q000378:metabolism; D008024:Ligands; D008566:Membranes / Q000378:metabolism; D051379:Mice; D048448:Phenylcarbamates; D016548:Prosencephalon / Q000378:metabolism; D011485:Protein Binding; D051381:Rats; D043885:Receptor, Cannabinoid, CB2; D043882:Receptors, Cannabinoid; D011955:Receptors, Drug / Q000032:analysis / Q000378:metabolism*; D013154:Spleen / Q000378:metabolism; D013237:Stereoisomerism; D013574:Synaptosomes / Q000378:metabolism
chemical_list: D002186:Cannabinoids; D002219:Carbamates; C469526:Cnr2 protein, rat; D008024:Ligands; D048448:Phenylcarbamates; D043885:Receptor, Cannabinoid, CB2; D043882:Receptors, Cannabinoid; D011955:Receptors, Drug; C080033:Chiralpak AD; D000688:Amylose