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Bioactive products from singlet oxygen photooxygenation of cannabinoids
Bioactive products from singlet oxygen photooxygenation of cannabinoids
- Source :
- European Journal of Medicinal Chemistry. 143:983-996
- Publication Year :
- 2018
- Publisher :
- Elsevier BV, 2018.
-
Abstract
- Photooxygenation of Δ8 tetrahydrocannabinol (Δ8-THC), Δ9 tetrahydrocannabinol (Δ9-THC), Δ9 tetrahydrocannabinolic 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.
- Subjects :
- 0301 basic medicine
Antifungal Agents
Cannabinoid receptor
medicine.medical_treatment
Plasmodium falciparum
Antiprotozoal Agents
Antineoplastic Agents
Ether
Microbial Sensitivity Tests
Photochemistry
Medicinal chemistry
Receptor, Cannabinoid, CB2
Antimalarials
03 medical and health sciences
chemistry.chemical_compound
0302 clinical medicine
Parasitic Sensitivity Tests
Receptor, Cannabinoid, CB1
Cell Line, Tumor
mental disorders
Drug Discovery
medicine
Humans
Tetrahydrocannabinol
Cell Proliferation
Leishmania major
Pharmacology
Bacteria
Singlet Oxygen
Cannabinoids
Singlet oxygen
organic chemicals
Organic Chemistry
Fungi
General Medicine
Photochemical Processes
Antimicrobial
Anti-Bacterial Agents
030104 developmental biology
chemistry
030220 oncology & carcinogenesis
Tetrahydrocannabinolic acid
Photooxygenation
lipids (amino acids, peptides, and proteins)
Cannabinoid
Drug Screening Assays, Antitumor
medicine.drug
Subjects
Details
- ISSN :
- 02235234
- Volume :
- 143
- Database :
- OpenAIRE
- Journal :
- European Journal of Medicinal Chemistry
- Accession number :
- edsair.doi.dedup.....204b775f5e3a521d99f00e8bfab390a4
- Full Text :
- https://doi.org/10.1016/j.ejmech.2017.11.043