Synthesis and testing of novel classical cannabinoids: exploring the side chain ligand binding pocket of the CB1 and CB2 receptors

A series of C3 cyclic side-chain analogues of classical cannabinoids were synthesized to probe the ligand binding pocket of the CB1 and CB2 receptors. The analogues were evaluated for CB1 and CB2 receptor binding affinities relative to Δ 8-THC. The C3 side-chain geometries of the analogues were stud...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry 2003-07, Vol.11 (14), p.3121-3132
Main Authors: Nadipuram, Asha K, Krishnamurthy, Mathangi, Ferreira, Antonio M, Li, Wei, Moore, Bob M
Format: Article
Language:English
Subjects:
Animals
Binding Sites
Biological and medical sciences
Cannabinoids - chemical synthesis
Cannabinoids - metabolism
Cell Membrane - metabolism
Humans
Ligands
Magnetic Resonance Spectroscopy
Medical sciences
Miscellaneous
Models, Molecular
Neuropharmacology
Neurotransmitters. Neurotransmission. Receptors
Pharmacology. Drug treatments
Protein Binding
Quantum Theory
Receptor, Cannabinoid, CB1 - chemistry
Receptor, Cannabinoid, CB1 - metabolism
Receptor, Cannabinoid, CB2 - chemistry
Receptor, Cannabinoid, CB2 - metabolism
Receptors, Cannabinoid - metabolism
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Summary:A series of C3 cyclic side-chain analogues of classical cannabinoids were synthesized to probe the ligand binding pocket of the CB1 and CB2 receptors. The analogues were evaluated for CB1 and CB2 receptor binding affinities relative to Δ 8-THC. The C3 side-chain geometries of the analogues were studied using high field NMR spectroscopy and quantum mechanical calculations. The results of these studies provide insights into the geometry of the ligand binding pocket of the CB1 and CB2 receptors. Graphic
ISSN:0968-0896
1464-3391
DOI:10.1016/S0968-0896(03)00238-4