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

M. L. Wise; K. Soderstrom; T. F. Murray; W. H. Gerwick

doi:10.1007/BF01922423

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

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

Research output: Contribution to journal › Article › peer-review

20 Scopus citations

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 language	English (US)
Pages (from-to)	88-92
Number of pages	5
Journal	Experientia
Volume	52
Issue number	1
DOIs	https://doi.org/10.1007/BF01922423
State	Published - Jan 1 1996
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry, Genetics and Molecular Biology(all)

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10.1007/BF01922423

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

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.",

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T1 - Synthesis and cannabinoid receptor binding activity of conjugated triene anandamide, a novel eicosanoid

AU - Wise, M. L.

AU - Soderstrom, K.

AU - Murray, T. F.

AU - Gerwick, W. H.

PY - 1996/1/1

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

Abstract

All Science Journal Classification (ASJC) codes

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