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

90 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

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 3 Good Health and Well-being

ASJC Scopus subject areas

Molecular Medicine
Drug Discovery

Access to Document

10.1021/jm050709m

Cite this

@article{aeebc3728f0b4f749a1aa7eaa4e2ad68,

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.",

author = "Shimon Ben-Shabat and Hanu{\v s}, \{Lum{\'i}r O.\} and Galia Katzavian and Ruth Gallily",

year = "2006",

month = feb,

day = "9",

doi = "10.1021/jm050709m",

language = "English",

volume = "49",

pages = "1113--1117",

journal = "Journal of Medicinal Chemistry",

issn = "0022-2623",

publisher = "American Chemical Society",

number = "3",

}

TY - JOUR

T1 - New cannabidiol derivatives

T2 - Synthesis, binding to cannabinoid receptor, and evaluation of their antiinflammatory activity

AU - Ben-Shabat, Shimon

AU - Hanuš, Lumír O.

AU - Katzavian, Galia

AU - Gallily, Ruth

PY - 2006/2/9

Y1 - 2006/2/9

N2 - 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.

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.

UR - https://www.scopus.com/pages/publications/32344437376

U2 - 10.1021/jm050709m

DO - 10.1021/jm050709m

M3 - Article

C2 - 16451075

AN - SCOPUS:32344437376

SN - 0022-2623

VL - 49

SP - 1113

EP - 1117

JO - Journal of Medicinal Chemistry

JF - Journal of Medicinal Chemistry

IS - 3

ER -

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

Abstract

UN SDGs

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this