HU-331: a cannabinoid quinone, with uncommon cytotoxic properties and low toxicity.
The oxidation of cannabis constituents has given rise to their corresponding quinones, which have been identified as cytotoxic agents. Out of these molecules the quinone of cannabidiol--the most abundant non-psychoactive cannabinoid in Cannabis sativa--has shown the highest cytotoxicity. This compound was named HU-331 and it exerts antiangiogenic properties, induces apoptosis to endothelial cells and inhibits topoisomerase II in nanomolar concentrations. Unlike other quinones, it is not cardiotoxic and does not induce the formation of free radicals. A comparative in vivo study in mice has shown HU-331 to be less toxic and more effective than the commonly used doxorubicin. This review summarises the properties of HU-331 and compares it with doxorubicin and other topoisomerase II inhibitors.
Peters
Maximilian
M
The Hebrew University, Department of Medicinal Chemistry and Natural Products, School of Pharmacy, Jerusalem, Israel.
Kogan
Natalya M
NM
D020533:Angiogenesis Inhibitors / Q000009:adverse effects / Q000494:pharmacology; D000818:Animals; D002185:Cannabidiol / Q000009:adverse effects / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology; D002186:Cannabinoids / Q000737:chemistry / Q000494:pharmacology*; D016923:Cell Death / Q000187:drug effects / Q000502:physiology; D003603:Cytotoxins / Q000009:adverse effects / Q000737:chemistry / Q000494:pharmacology*; D006801:Humans; D011809:Quinones / Q000737:chemistry / Q000494:pharmacology*; D014407:Tumor Cells, Cultured
D020533:Angiogenesis Inhibitors; D002186:Cannabinoids; D003603:Cytotoxins; D011809:Quinones; C073718:cannabidiol hydroxyquinone; D002185:Cannabidiol