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Chem Biol Drug Des. 2015 Dec;86(6):1451-7. doi: 10.1111/cbdd.12612. Epub 2015 Aug 7.

Synthesis, Characterization, and Anticancer Activity of Novel Lipophilic Emodin Cationic Derivatives.

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College of Chemistry, Fuzhou University, Fuzhou, Fujian, 350108, China.
Research Institute of Photocatalysis, State Key Laboratory of Photocatalysis on Energy and Environment, Fuzhou, Fujian, 350002, China.
Department of Pharmaceutics, University of Washington, Seattle, WA, 98105, USA.


Seventeen novel emodin derivatives were synthesized, and the structures were confirmed by IR, H NMR, MS, and elemental analysis. The cytotoxic activity of the derivatives was evaluated against A375, BGC-823, HepG2, and HELF cells by MTT assay. Compound 9a with highest potency and low toxicity was selected to further investigate its detailed molecular mechanism. The lead compound 9a induced a loss of the mitochondrial transmembrane potential (▵Ψm), an increase in reactive oxygen species (ROS), release of cytochrome c and activation of caspase-3 and caspase-9. In addition, the confocal study showed that emodin derivative 9a (containing asymmetric hydrocarbon tails) was mainly localized in mitochondria, demonstrating a key role of the mitochondria-mediated apoptosis pathway in cancer cells. Taken together, the results demonstrate that embodin derivative 9a preferentially regulates the ROS-mediated apoptosis in A375 cells through the induction of cytochrome c expression and activation of caspase-3 and caspase-9 proteins.


apoptosis; emodin derivative; reactive oxygen species; synthesis

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