Synthesis and cannabinoid receptor binding activity of conjugated triene anandamide, a novel eicosanoid
- 38 Downloads
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.
Key wordsCannabinoid receptor polyenoic fatty-acid isomerase marine enzyme anandamide red algae
Unable to display preview. Download preview PDF.
- 4.Evershed, R. P. in: Handbook of Derivatives for Chromatography, 2nd edn p. 59. Eds K. Blau and J. Halket, John Wiley & Sons, Chichester (England) 1993.Google Scholar
- 8.Wolff, I. A., and Miwa, T. K., J. Am. Oil chem. Soc.42 (1965) 208.Google Scholar
- 9.Deutsch, D. G., and Chin, S. A., Biochem. Pharmac.46 (1993) 791.Google Scholar
- 10.Childers, S. R., Sexton, T., and Roy, M. B., Biochem. Pharmac.47 (1994) 711.Google Scholar
- 11.Pinto, J. C., Potie, F., Rice, K. C., Boring, D., Johnson, M. R., Evans, D. M., Wilken, G. H., Cantrell, C. H., and Howlett, A. C., Molec. Pharmac.46 (1994) 516.Google Scholar