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Molecules 2013, 18(12), 15750-15768; doi:10.3390/molecules181215750
Article

Design, Synthesis and Evaluation of N13-Substituted Evodiamine Derivatives against Human Cancer Cell Lines

1, 1, 1, 2, 1,*  and 1,*
1 School of Chemistry and Chemical Engineering, Sun Yat-sen University, Guangzhou 510275, China 2 College of Chemistry and Life Science, Guangxi Teachers Education University, Nanning 530001, China
* Authors to whom correspondence should be addressed.
Received: 23 October 2013 / Revised: 7 November 2013 / Accepted: 12 November 2013 / Published: 17 December 2013
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Abstract

Attempting to improve the anticancer activity and solubility of evodiamine in simulated gastric fluid (SGF) and simulated intestinal fluid (SIF) solutions, thirty-eight N13-substituted evodiamine derivatives were designed, synthesized and tested for antitumor activities against six kinds of human cancer cell lines, namely prostate cancer (DU-145 and PC-3), lung cancer (H460), breast cancer (MCF-7), colon cancer (HCT-5) and glioblastoma (SF-268). The solubility of these compounds in SGF and SIF solutions was evaluated, and apoptosis induced by 2-2, 2-3, 2-16 and 3-2 was determined. The results showed: (1) among all compounds examined, 2-16 showed the highest antitumor activity and a broader spectrum of activity, with IC50 values ranging from 1–2 µM; (2) their solubility was obviously improved; (3) 2-3, 2-16 and 3-2 had a significant impact inducing apoptosis in some cancer cell lines. The preliminary structure-activity relationships of these derivatives were discussed.
Keywords: N13-substituted evodiamine derivatives; antitumor activity; apoptosis; solubility N13-substituted evodiamine derivatives; antitumor activity; apoptosis; solubility
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Song, S.; Chen, Z.; Li, S.; Huang, Y.; Wan, Y.; Song, H. Design, Synthesis and Evaluation of N13-Substituted Evodiamine Derivatives against Human Cancer Cell Lines. Molecules 2013, 18, 15750-15768.

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