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Literature DB >> 16451075

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

Shimon Ben-Shabat¹, Lumír O Hanus, Galia Katzavian, Ruth Gallily.

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-alpha) by murine macrophages, and for their binding to the cannabinoid receptor (CB(1)). 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.

Entities: Chemical Gene Species

Mesh：

Substances：

Year: 2006 PMID： 16451075 DOI： 10.1021/jm050709m

Source DB: PubMed Journal: J Med Chem ISSN： 0022-2623 Impact factor: 7.446

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Cited

23 in total

1. HU-444, a Novel, Potent Anti-Inflammatory, Nonpsychotropic Cannabinoid.

Authors: Christeene G Haj; Percy F Sumariwalla; Lumír Hanuš; Natalya M Kogan; Zhana Yektin; Raphael Mechoulam; Mark Feldmann; Ruth Gallily
Journal: J Pharmacol Exp Ther Date: 2015-08-13 Impact factor: 4.030

2. Cannabidiol improves brain and liver function in a fulminant hepatic failure-induced model of hepatic encephalopathy in mice.

Authors: Y Avraham; Nc Grigoriadis; T Poutahidis; L Vorobiev; I Magen; Y Ilan; R Mechoulam; Em Berry
Journal: Br J Pharmacol Date: 2011-04 Impact factor: 8.739

3. Allosteric and orthosteric pharmacology of cannabidiol and cannabidiol-dimethylheptyl at the type 1 and type 2 cannabinoid receptors.

Authors: Mylyne Tham; Orhan Yilmaz; Mariam Alaverdashvili; Melanie E M Kelly; Eileen M Denovan-Wright; Robert B Laprairie
Journal: Br J Pharmacol Date: 2018-08-10 Impact factor: 8.739

9. Cannabinoids Delta(9)-tetrahydrocannabinol and cannabidiol differentially inhibit the lipopolysaccharide-activated NF-kappaB and interferon-beta/STAT proinflammatory pathways in BV-2 microglial cells.

Authors: Ewa Kozela; Maciej Pietr; Ana Juknat; Neta Rimmerman; Rivka Levy; Zvi Vogel
Journal: J Biol Chem Date: 2009-11-12 Impact factor: 5.157

Review 10. Cannabinoids, endocannabinoids, and related analogs in inflammation.

Authors: Sumner H Burstein; Robert B Zurier
Journal: AAPS J Date: 2009-02-06 Impact factor: 4.009

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

1. HU-444, a Novel, Potent Anti-Inflammatory, Nonpsychotropic Cannabinoid.

2. Cannabidiol improves brain and liver function in a fulminant hepatic failure-induced model of hepatic encephalopathy in mice.

3. Allosteric and orthosteric pharmacology of cannabidiol and cannabidiol-dimethylheptyl at the type 1 and type 2 cannabinoid receptors.

4. Synthetic and Natural Derivatives of Cannabidiol.

5. Cannabidiol ameliorates cognitive and motor impairments in bile-duct ligated mice via 5-HT1A receptor activation.

6. Cannabidiol arrests onset of autoimmune diabetes in NOD mice.

7. Discovery of KLS-13019, a Cannabidiol-Derived Neuroprotective Agent, with Improved Potency, Safety, and Permeability.

Review 8. The Essential Medicinal Chemistry of Cannabidiol (CBD).

9. Cannabinoids Delta(9)-tetrahydrocannabinol and cannabidiol differentially inhibit the lipopolysaccharide-activated NF-kappaB and interferon-beta/STAT proinflammatory pathways in BV-2 microglial cells.

Review 10. Cannabinoids, endocannabinoids, and related analogs in inflammation.