Design, synthesis, and anticancer evaluation of long-chain alkoxylated mono-carbonyl analogues of curcumin

European Journal of Medicinal Chemistry
Qiaoyou WengGuang Liang

Abstract

Curcumin is a nontoxic phenolic compound that modulates the activity of several cellular targets that have been linked with cancers and other chronic diseases. However, the efficacy of curcumin in the clinic has been limited by its poor bioavailability and rapid metabolism in vivo. We have previously reported the design and discovery of series of 5-carbon linker-containing mono-carbonyl analogues of curcumin (MACs) as anti-cancer agents. In continuation of our ongoing research, we designed and synthesized 37 novel long-chain alkoxylated MACs for anti-cancer evaluation here. The MTS assay was used to determine the cytotoxicity of compounds in gastrointestinal cancer cells. Compounds 5, 28, and 29 showed strongest inhibition against gastric cancer cell proliferation and were subjected to further analysis. The effects of 5, 28, and 29 on cell apoptosis were measured by flow cytometry. Expression levels of Bcl-2, cleaved poly ADP-ribose polymerase (PARP), and pro-caspase-3 were detected by western blotting. Compounds 5, 28, and 29 induced apoptosis in human gastric carcinoma cells, increased PARP cleavage, and decreased expression of Bcl-2 and pro-caspase-3 protein. We then showed that compound 28, which possessed the strongest act...Continue Reading

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Citations

Nov 2, 2015·Tumour Biology : the Journal of the International Society for Oncodevelopmental Biology and Medicine·Yiqun XiaGuang Liang
Sep 8, 2018·Journal of Cellular Physiology·Nastaran BaratiAmirhossein Sahebkar
May 17, 2019·Expert Opinion on Drug Discovery·Eirini Chainoglou, Dimitra Hadjipavlou-Litina
Aug 21, 2020·Nutrition and Cancer·Afsane Bahrami, Gordon A Ferns
Apr 15, 2017·BioMed Research International·Jian ChenWulan Li
Jul 25, 2019·European Journal of Medicinal Chemistry·Shijie ZhaoYumeng Wei
Sep 4, 2019·European Journal of Medicinal Chemistry·Sawsan A NoureddinKhalid O Al-Footy
Sep 27, 2019·European Journal of Medicinal Chemistry·Poh Yen KhorKok Wai Lam

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