New cannabidiol derivatives: Synthesis, binding to cannabinoid receptor, and evaluation of their antiinflammatory activity

Shimon Ben-Shabat; Lumír O. Hanuš; Galia Katzavian; Ruth Gallily

doi:10.1021/jm050709m

New cannabidiol derivatives: Synthesis, binding to cannabinoid receptor, and evaluation of their antiinflammatory activity

Shimon Ben-Shabat, Lumír O. Hanuš, Galia Katzavian, Ruth Gallily

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

82 Scopus citations

Abstract

Cannabidiol (CBD) and cannabidiol dimethyl hephtyl (CBD-DMH) were hydrogenated to give four different epimers. The new derivatives were evaluated for their ability to modulate the production of reactive oxygen intermediates (ROI), nitric oxide (NO), and tumor necrosis factor (TNF-α) by murine macrophages, and for their binding to the cannabinoid receptor (CB₁). Surprisingly, we found that these derivatives exhibit good binding to CB ₁. In addition hydrogenated CBD and CBD-DMH demonstrate bioactivities different from their original compounds.

Original language	English
Pages (from-to)	1113-1117
Number of pages	5
Journal	Journal of Medicinal Chemistry
Volume	49
Issue number	3
DOIs	https://doi.org/10.1021/jm050709m
State	Published - 9 Feb 2006

ASJC Scopus subject areas

Molecular Medicine
Drug Discovery

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10.1021/jm050709m

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title = "New cannabidiol derivatives: Synthesis, binding to cannabinoid receptor, and evaluation of their antiinflammatory activity",

abstract = "Cannabidiol (CBD) and cannabidiol dimethyl hephtyl (CBD-DMH) were hydrogenated to give four different epimers. The new derivatives were evaluated for their ability to modulate the production of reactive oxygen intermediates (ROI), nitric oxide (NO), and tumor necrosis factor (TNF-α) by murine macrophages, and for their binding to the cannabinoid receptor (CB1). Surprisingly, we found that these derivatives exhibit good binding to CB 1. In addition hydrogenated CBD and CBD-DMH demonstrate bioactivities different from their original compounds.",

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AU - Ben-Shabat, Shimon

AU - Hanuš, Lumír O.

AU - Katzavian, Galia

AU - Gallily, Ruth

PY - 2006/2/9

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AB - Cannabidiol (CBD) and cannabidiol dimethyl hephtyl (CBD-DMH) were hydrogenated to give four different epimers. The new derivatives were evaluated for their ability to modulate the production of reactive oxygen intermediates (ROI), nitric oxide (NO), and tumor necrosis factor (TNF-α) by murine macrophages, and for their binding to the cannabinoid receptor (CB1). Surprisingly, we found that these derivatives exhibit good binding to CB 1. In addition hydrogenated CBD and CBD-DMH demonstrate bioactivities different from their original compounds.

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New cannabidiol derivatives: Synthesis, binding to cannabinoid receptor, and evaluation of their antiinflammatory activity

Abstract

ASJC Scopus subject areas

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