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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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

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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