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

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 ca...

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Autores principales: Song, Senchuan, Chen, Zhiyong, Li, Shaoxue, Huang, Yanmin, Wan, Yiqian, Song, Huacan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2013
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6270516/
https://www.ncbi.nlm.nih.gov/pubmed/24352027
http://dx.doi.org/10.3390/molecules181215750
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author Song, Senchuan
Chen, Zhiyong
Li, Shaoxue
Huang, Yanmin
Wan, Yiqian
Song, Huacan
author_facet Song, Senchuan
Chen, Zhiyong
Li, Shaoxue
Huang, Yanmin
Wan, Yiqian
Song, Huacan
author_sort Song, Senchuan
collection PubMed
description 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 IC(50) 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.
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spelling pubmed-62705162018-12-20 Design, Synthesis and Evaluation of N13-Substituted Evodiamine Derivatives against Human Cancer Cell Lines Song, Senchuan Chen, Zhiyong Li, Shaoxue Huang, Yanmin Wan, Yiqian Song, Huacan Molecules Article 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 IC(50) 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. MDPI 2013-12-17 /pmc/articles/PMC6270516/ /pubmed/24352027 http://dx.doi.org/10.3390/molecules181215750 Text en © 2013 by the authors; licensee MDPI, Basel, Switzerland. http://creativecommons.org/licenses/by/3.0/ This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Song, Senchuan
Chen, Zhiyong
Li, Shaoxue
Huang, Yanmin
Wan, Yiqian
Song, Huacan
Design, Synthesis and Evaluation of N13-Substituted Evodiamine Derivatives against Human Cancer Cell Lines
title Design, Synthesis and Evaluation of N13-Substituted Evodiamine Derivatives against Human Cancer Cell Lines
title_full Design, Synthesis and Evaluation of N13-Substituted Evodiamine Derivatives against Human Cancer Cell Lines
title_fullStr Design, Synthesis and Evaluation of N13-Substituted Evodiamine Derivatives against Human Cancer Cell Lines
title_full_unstemmed Design, Synthesis and Evaluation of N13-Substituted Evodiamine Derivatives against Human Cancer Cell Lines
title_short Design, Synthesis and Evaluation of N13-Substituted Evodiamine Derivatives against Human Cancer Cell Lines
title_sort design, synthesis and evaluation of n13-substituted evodiamine derivatives against human cancer cell lines
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6270516/
https://www.ncbi.nlm.nih.gov/pubmed/24352027
http://dx.doi.org/10.3390/molecules181215750
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