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Open AccessArticle

Synthesis and Biological Evaluation of Curcumin Derivatives with Water-Soluble Groups as Potential Antitumor Agents: An in Vitro Investigation Using Tumor Cell Lines

Department of Natural Products Chemistry, Key Lab of Chemical Biology (MOE), School of Pharmaceutical Sciences, Shandong University, No. 44 West Wenhua Road, Jinan 250012, China
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Academic Editor: Jean Jacques Vanden Eynde
Molecules 2015, 20(12), 21501-21514; https://doi.org/10.3390/molecules201219772
Received: 26 October 2015 / Revised: 24 November 2015 / Accepted: 26 November 2015 / Published: 2 December 2015
(This article belongs to the Section Medicinal Chemistry)
Three series of curcumin derivatives including phosphorylated, etherified, and esterified products of curcumin were synthesized, and their anti-tumor activities were assessed against human breast cancer MCF-7, hepatocellular carcinoma Hep-G2, and human cervical carcinoma HeLa cells. Compared with curcumin, compounds 3, 8, and 9 exhibited stronger antitumor cell line growth activities against HeLa cells. Compound 12 also showed higher antitumor cell line growth activities on MCF-7 cells than curcumin. Among them, 4-((1E,6E)-7-(4-Hydroxy-3-methoxyphenyl)-3,5-dioxohepta-1,6-dienyl)-2-methoxyphenyl dihydrogen phosphate(3) showed the strongest activity with an half maximal inhibitory concentration (IC50) of 6.78 µM against HeLa cells compared with curcumin with an IC50 of 17.67 µM. Stabilities of representatives of the three series were tested in rabbit plasma in vitro, and compounds 3 and 4 slowly released curcumin in plasma. The effect of compound 3 on HeLa cell apoptosis was determined by examining morphological changes by DAPI (4′,6-diamidino-2-phenylindole) staining as well as Annexin V-FITC/ Propidium Iodide (PI) double staining and flow cytometry. The results showed that 3 induced cellular apoptosis in a dose-dependent manner. Together our findings show that 3 merits further investigation as a new potential antitumor drug candidate. View Full-Text
Keywords: curcumin; curcumin derivatives; synthesis; antitumor cell line growth activity; apoptosis curcumin; curcumin derivatives; synthesis; antitumor cell line growth activity; apoptosis
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MDPI and ACS Style

Ding, L.; Ma, S.; Lou, H.; Sun, L.; Ji, M. Synthesis and Biological Evaluation of Curcumin Derivatives with Water-Soluble Groups as Potential Antitumor Agents: An in Vitro Investigation Using Tumor Cell Lines. Molecules 2015, 20, 21501-21514.

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