The anandamide membrane transporter. Structure-activity relationships of anandamide and oleoylethanolamine analogs with phenyl rings in the polar head group region.
A new series of anandamide and N-oleoylethanolamine analogs, most of which with aromatic moieties in the head group region, has been synthesized and evaluated as inhibitors of anandamide uptake. Some of them efficaciously inhibit the uptake process with K(i) values in the low micromolar range (2.4-21.2microM). Strict structural requisites are needed to observe a significant inhibition and in no case inhibition of fatty acid amidohydrolase overlaps with inhibition of anandamide uptake.
Di Marzo
Vincenzo
V
Endocannabinoid Research Group, Institute of Biomolecular Chemistry, Consiglio Nazionale delle Ricerche, Via Campi Flegrei 34, 80078 Pozzuoli, Napoli, Italy.
Ligresti
Alessia
A
Morera
Enrico
E
Nalli
Marianna
M
Ortar
Giorgio
G
D001095:Arachidonic Acids / Q000737:chemistry* / Q000378:metabolism; D002460:Cell Line; D063388:Endocannabinoids; D006801:Humans; D007473:Ion Channels / Q000737:chemistry; D007700:Kinetics; D049990:Membrane Transport Modulators; D026901:Membrane Transport Proteins / Q000037:antagonists & inhibitors*; D009829:Oleic Acids / Q000737:chemistry*; D053284:Polyunsaturated Alkamides; D011869:Radioligand Assay; D043884:Receptor, Cannabinoid, CB1 / Q000737:chemistry; D043885:Receptor, Cannabinoid, CB2 / Q000737:chemistry; D055672:Static Electricity; D013329:Structure-Activity Relationship; D050916:TRPV Cation Channels
D001095:Arachidonic Acids; D063388:Endocannabinoids; D007473:Ion Channels; D049990:Membrane Transport Modulators; D026901:Membrane Transport Proteins; D009829:Oleic Acids; D053284:Polyunsaturated Alkamides; D043884:Receptor, Cannabinoid, CB1; D043885:Receptor, Cannabinoid, CB2; D050916:TRPV Cation Channels; C494482:TRPV1 protein, human; C488250:oleoylethanolamide; C078814:anandamide