2,3-Dimethoxy-5-methyl-p-benzoquinone

2,3-Dimethoxy-5-methyl-p-benzoquinone, also known as coenzyme Q₀, is a key intermediate in the synthesis of coenzyme Q, coenzyme Q₁₀, other ubiquinones, and vitamin E.^1,2 It inhibits the growth of SKOV-3, A2780, and A2870/CP70 human ovarian carcinoma cells (IC₅₀s = 26.6, 27.3, and 28.4 µM, respectively) with a cytotoxic concentration of greater than 40 µM for non-cancerous ovarian surface epithelial cells.³ It halts the cell cycle at the G₂/M phase, increases the production of reactive oxygen species (ROS), and induces autophagy and apoptosis in SKOV-3 cells. 2,3-Dimethoxy-5-methyl-p-benzoquinone downregulates the protooncogene HER-2 and decreases the protein levels of phosphorylated AKT and mTOR in SKOV-3 cells. It also decreases the incidence of tumors and tumor burden in a SKOV-3 human ovarian carcinoma mouse xenograft model when administered at a dose of 2.5 mg/kg every four days.

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1. Zalomaeva, O.V., Evtushok, V.Y., Maksimov, G.M., et al. Synthesis of coenzyme Q0 through divanadium-catalyzed oxidation of 3,4,5-trimethoxytoluene with hydrogen peroxide. Dalton Trans. 46(16), 5202-5209 (2017).

2. Adam, W., Herrmann, W.A., Lin, J., et al. Catalytic oxidation of phenols to p-quinones with the hydrogen peroxide and methyltrioxorhenium(VII) system. The Journal of Organic Chemistry 59(26), 8281-8283 (1994).

3. Hsue, Y.C., Tsai, T.J., Korivi, M., et al. Antitumor properties of Coenzyme Q0 against human ovarian carcinoma cells via induction of ROS-mediated apoptosis and cytoprotective autophagy. Sci. Rep. 7(1), 8062 (2017).