Journal
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
Volume 16, Issue 1, Pages 138-141Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmcl.2005.09.023
Keywords
cannabinoid; anandamide; CB1; CB2; receptor
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We investigated the structure-activity relationships for the interactions of fatty acid amide analogs of the endocannabinoid anandamide with human recombinant cannabinoid receptors. Thirty-five novel fatty acid amides were synthesized using five different types of acyl chains and 11 different aromatic amine 'heads.' Although none of the new compounds was a more potent ligand than anandamide, we identified three amine groups capable of improving the metabolic stability of arachidonoylamides and their CB1/CB2 selectivity ratio to over 20-fold, and several aromatic amines capable of improving the affinity of short chain or monosaturated fatty acids for cannabinoid CB1 receptors. For the first time a tertiary amide of arachidonic acid was found to possess moderate affinity (K-i = 300 nM) for cannabinoid CB1, but not CB2, receptors. (c) 2005 Elsevier Ltd. All rights reserved.
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