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 recepto...

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Veröffentlicht in:	Journal of biochemical and biophysical methods 2002-12, Vol.54 (1), p.415-422
Hauptverfasser:	Thakur, Ganesh A, Palmer, Sonya L, Harrington, Paul E, Stergiades, Ioanna A, Tius, Marcus A, Makriyannis, Alexandros
Format:	Artikel
Sprache:	eng
Schlagworte:	Amylose - analogs & derivatives Animals Cannabinoid receptors Cannabinoids - analysis Cannabinoids - chemistry Cannabinoids - classification Cannabinoids - metabolism Carbamates ChiralPak AD column Chromatography, High Pressure Liquid - instrumentation Chromatography, High Pressure Liquid - methods Humans Hybrid cannabinoids Kidney - embryology Kidney - metabolism Ligands Membranes - metabolism Mice Phenylcarbamates Prosencephalon - metabolism Protein Binding Rats Receptor, Cannabinoid, CB2 Receptors, Cannabinoid Receptors, Drug - analysis Receptors, Drug - metabolism Spleen - metabolism Stereoisomerism Synaptosomes - metabolism Δ 9-THC
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Zusammenfassung:	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.
ISSN:	0165-022X 1872-857X
DOI:	10.1016/S0165-022X(02)00144-6