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European journal of medicinal chemistry v.143, 2018년, pp.983 - 996   SCI SCIE
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Bioactive products from singlet oxygen photooxygenation of cannabinoids

Galal Osman, Ahmed (National Center for Natural Products Research, The University of Mississippi, University, MS 38677, United States ) ; Elokely, Khaled M. (Institute for Computational Molecular Science, Temple University, Philadelphia, PA 19122, United States ) ; Yadav, Vivek K. (Institute for Computational Molecular Science, Temple University, Philadelphia, PA 19122, United States ) ; Carvalho, Paulo (Feik School of Pharmacy, University of the Incarnate Word, San Antonio, TX 78209, United States ) ; Radwan, Mohamed (National Center for Natural Products Research, The University of Mississippi, University, MS 38677, United States ) ; Slade, Desmond (MRI Global, 425 Volker Boulevard, Kansas City, MO, United States ) ; Gul, Waseem (National Center for Natural Products Research, The University of Mississippi, University, MS 38677, United States ) ; Khan, Shabana (National Center for Natural Products Research, The University of Mississippi, University, MS 38677, United States ) ; Dale, Olivia R. (National Center for Natural Products Research, The University of Mississippi, University, MS 38677, United States ) ; Husni, Afeef S. (Department of of BioMolecular Sciences, Uni ) ; Klein, Michael L. ; Cutler, Stephen J. ; Ross, Samir A. ; ElSohly, Mahmoud A. ;
  • 초록  

    Abstract Photooxygenation of Δ 8 tetrahydrocannabinol (Δ 8 -THC), Δ 9 tetrahydrocannabinol (Δ 9 -THC), Δ 9 tetrahydrocannabinolic acid (Δ 9 -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 CB 1 and CB 2 led to the identification of 7 and 21 as CB 1 partial agonists with Ki values of 0.043 μM and 0.048 μM, respectively and 23 as a cannabinoid with high binding affinity for CB 2 with Ki value of 0.0095 μM, but much less affinity towards CB 1 (Ki 0.467 μM). The synthesized compounds showed cytotoxic activity against cancer cell lines (SK-MEL, KB, BT-549, and SK-OV-3) with IC 50 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. Highlights Photooxygenation of cannabinol derivatives yielded 18 new oxygenated compounds. Products exhibited anticancer, antimicrobial, and antileishmanial effects. One derivative showed better antileishmanial activity than standard drugs. Two derivatives are CB1 partial agonists, one shows high CB2 binding affinity. Photooxygenation may be a practical way to synthesize cannabinoid metabolites. Graphical abstract [DISPLAY OMISSION]


  • 주제어

    Cannabinoids .   Photooxygenation .   CB1 agonists .   Antimicrobial .   Anticancer .   Antileishmanial.  

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