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- W2040400211 abstract "To investigate if certain acylethanolamides bind to both cannabinoid (CB(1) and CB(2)) and vanilloid TRPV1 receptors because of their conformational flexibility, we introduced a methylene lock on their ethanolamine head, thereby generating a cyclopropane ring with two stereogenic centers and chiral cis/trans diastereomers with different topology of presentation to binding sites. After resolution by chiral-phase HPLC, diastereo- and enantiopure arachidonoyl-, oleoyl-, and palmitoylcyclopropanolamides were tested in assays of CB(1), CB(2), and TRPV1 activity. Diastereodifferentiation between pairs of cis-trans isomers was observed only for TRPV1 activity, with poor enantiodifferentiation. Methylenation introduced (i) CB(1) receptor affinity in oleoylethanolamide while increasing in a diastereoselective way its activity at TRPV1 and (ii) strong diastereoselective activity at TRPV1, but not cannabinoid, receptors in the otherwise inactive palmitoylethanolamide. These results show that the N-alkyl group of acylethanolamides has a different role in their interaction with cannabinoid and vanilloid receptors and that acylcyclopropanolamides qualify as CB(1)/TRPV1 hybrids of potential therapeutic utility." @default.
- W2040400211 created "2016-06-24" @default.
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- W2040400211 date "2009-04-10" @default.
- W2040400211 modified "2023-10-15" @default.
- W2040400211 title "Conformationally Constrained Fatty Acid Ethanolamides as Cannabinoid and Vanilloid Receptor Probes" @default.
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- W2040400211 doi "https://doi.org/10.1021/jm900130m" @default.
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