Cannabichromene (CBC) is a minor cannabinoid present in <i>Cannabis sativa</i>. Similar to the more widely known cannabinoids, THC and CBD, CBC exhibits many biological activities, including antibacterial and anticancer properties. In this study, a series of CBC based compounds were synthesized, containing an oxime ester moiety instead of a pentyl side chain. The CBC oxime esters, together with the precursor CBC oxime, were evaluated for their anticancer potential by determining their anti-mitotic activity on sea urchin embryos. The compounds were tested at 5 µM, 10 µM, 25 µM, and 50 µM, and the embryos were evaluated after 60, 90, 120 and 150 minutes. The oxime and oxime esters inhibited the rate of mitosis of sea urchin embryos in a concentration-dependent manner. At the 50 mM concentration, most of the embryos showed little or no division. In order to probe apoptosis as a potential mechanism of mitosis inhibition, embryos exposed to the CBC oxime were stained with CellEvent Caspase 3/7 fluorescent dye. The presence of active caspases was detected in a concentration dependent response, signifying that the anti-mitotic activity was due to apoptosis. Further studies will be conducted to evaluate the effects of the CBC oxime derivatives on DNA cleavage and proliferation of human cancer cells.

Synthesis and anticancer potential of cannabichromene-based oxime ester derivatives

ACS Spring Meeting 2021

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