Synthesis and cannabinoid receptor binding activity of conjugated triene anandamide, a novel eicosanoid

M. L. Wise, K. Soderstrom, Thomas F. Murray, W. H. Gerwick

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Abstract

A polyenoic fatty-acid isomerase (PFI) from a red marine alga was used to convert anandamide (5Z,8Z,11Z,14Z-eicosatetraenoyl-N-ethanolamide to the 5Z,7E,9E,14Z-eicosatetraenoyl-N-ethanolamide 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.

Original languageEnglish
Pages (from-to)88-92
Number of pages5
JournalExperientia
Volume52
Issue number1
DOIs
Publication statusPublished - Jan 1996
Externally publishedYes

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All Science Journal Classification (ASJC) codes

  • Biochemistry, Genetics and Molecular Biology(all)

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