Enantiomeric resolution of a novel chiral cannabinoid receptor ligand.
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.
Thakur
Ganesh A
GA
Department of Pharmaceutical Sciences and the Center for Drug Discovery, University of Connecticut, 372 Fairfield Road, Storrs, CT 06269, USA.
Palmer
Sonya L
SL
Harrington
Paul E
PE
Stergiades
Ioanna A
IA
Tius
Marcus A
MA
Makriyannis
Alexandros
A
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
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