Canna~Fangled Abstracts

Bioactive products from singlet oxygen photooxygenation of cannabinoids.

By November 21, 2017No Comments
Eur J Med Chem. 2017 Nov 21;143:983-996. doi: 10.1016/j.ejmech.2017.11.043.
[Epub ahead of print]

Abstract

PM 2 site 207Photooxygenation of Δ8 tetrahydrocannabinol (Δ8-THC), Δ9 tetrahydrocannabinol (Δ9-THC), Δ9tetrahydrocannabinolic acid (Δ9-THCA) and some derivatives (acetate, tosylate and methyl ether) yielded 24 oxygenated derivatives, 18 of which were new and 6 were previously reported, including allyl alcohols, ethers, quinones, hydroperoxides, and epoxides. Testing these compounds for their modulatory effect on cannabinoid receptors CB1 and CB2 led to the identification of 7 and 21 as CB1 partial agonists with Ki values of 0.043 μM and 0.048 μM, respectively and 23 as a cannabinoid with high binding affinity for CB2 with Ki value of 0.0095 μM, but much less affinity towards CB1 (Ki 0.467 μM). The synthesized compounds showed cytotoxic activity against cancer cell lines (SK-MEL, KB, BT-549, and SK-OV-3) with IC50 values ranging from 4.2 to 8.5 μg/mL. Several of those compounds showed antimicrobial, antimalarial and antileishmanial activities, with compound 14 being the most potent against various pathogens.

KEYWORDS:

Anticancer; Antileishmanial; Antimicrobial; CB(1) agonists; Cannabinoids; Photooxygenation

PMID: 29232588
DOI: 10.1016/j.ejmech.2017.11.043
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