Structural requirements for arachidonylethanolamide interaction with CB1 and CB2 cannabinoid receptors : pharmacology of the carbonyl and ethanolamide groups

Analogs of arachidonylethanolamide (anandamide) were prepared to investigate the structural requirements for ligand binding to and activation of the CB1 and CB2 cannabinoid receptors. The importance of the presence and the placement of the carbonyl was examined with analogs lacking the carbonyl or w...

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Bibliographic Details
Published in:Prostaglandins, leukotrienes and essential fatty acids leukotrienes and essential fatty acids, 1998-08, Vol.59 (2), p.111-118
Main Authors: BERGLUND, B. A, BORING, D. L, WILKEN, G. H, MAKRIYANNIS, A, HOWLETT, A. C
Format: Article
Language:English
Subjects:
Adenylyl Cyclases - metabolism
Animals
Arachidonic Acids - chemistry
Arachidonic Acids - metabolism
Arachidonic Acids - pharmacology
Binding Sites
Biological and medical sciences
Brain - metabolism
Cannabinoids - metabolism
Cell Line
Cell Membrane - drug effects
Endocannabinoids
GTP-Binding Proteins - metabolism
Guanosine 5'-O-(3-Thiotriphosphate) - metabolism
Humans
Ligands
Medical sciences
Neuropharmacology
Neurotransmitters. Neurotransmission. Receptors
Palatine Tonsil - metabolism
Peptidergic system (neuropeptide, opioid peptide, opiates...). Adenosinergic and purinergic systems
Pharmacology. Drug treatments
Phenanthridines - pharmacology
Polyunsaturated Alkamides
Rats
Receptor, Cannabinoid, CB2
Receptors, Cannabinoid
Receptors, Drug - chemistry
Receptors, Drug - metabolism
Signal Transduction - drug effects
Stereoisomerism
Thermodynamics
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Summary:Analogs of arachidonylethanolamide (anandamide) were prepared to investigate the structural requirements for ligand binding to and activation of the CB1 and CB2 cannabinoid receptors. The importance of the presence and the placement of the carbonyl was examined with analogs lacking the carbonyl or with the carbonyl amide order reversed. The presence and location of the carbonyl is essential for high-affinity binding to both cannabinoid receptor subtypes, and for determination of signal transduction via G-proteins. Methyl groups were substituted on the 1'- and 2'-positions of arachidonylethanolamide and the significance of chirality was examined. Stereochemical differences in the ethanolamide group influence the affinity for both cannabinoid receptor subtypes and the signal transduction capabilities of the methanandamide derivatives.
ISSN:0952-3278
1532-2823
DOI:10.1016/S0952-3278(98)90089-8