Synthesis and cannabinoid receptor binding activity of conjugated triene anandamide, a novel eicosanoid.
A polyenoic fatty-acid isomerase (PFI) from a red marine alga was used to convert anandamide (5Z,8Z,11Z,14Z-eicosatetraenoyl-N-ethan olamide) to the 5Z,7E,9E,14Z-eicosatetraenoyl-N-ethanol amide isomer. This novel eicosanoid, termed conjugated triene anandamide (CTA), was assessed for its ability to bind to the cannabinoid receptor in rat brain membrane preparations. CTA is a high affinity cannabimimetic substance whose novel structure provides new insight into structure-activity relationships of cannabinoid receptor ligands. These experiments illustrate the utility of enzymes isolated from marine organisms in the development of pharmacological probes.
Wise
M L
ML
Department of Biochemistry and Biophysics, Oregon State University, Corvallis 97331, USA.
Soderstrom
K
K
Murray
T F
TF
Gerwick
W H
WH
D000818:Animals; D001095:Arachidonic Acids / Q000138:chemical synthesis* / Q000378:metabolism; D001921:Brain / Q000378:metabolism*; D002186:Cannabinoids / Q000378:metabolism; D002462:Cell Membrane / Q000378:metabolism; D015777:Eicosanoids / Q000138:chemical synthesis* / Q000378:metabolism; D063388:Endocannabinoids; D056890:Eukaryota / Q000378:metabolism; D053284:Polyunsaturated Alkamides; D011869:Radioligand Assay; D051381:Rats; D043882:Receptors, Cannabinoid; D011955:Receptors, Drug / Q000378:metabolism*
D001095:Arachidonic Acids; D002186:Cannabinoids; D015777:Eicosanoids; D063388:Endocannabinoids; D053284:Polyunsaturated Alkamides; D043882:Receptors, Cannabinoid; D011955:Receptors, Drug; C078814:anandamide