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

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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Main Authors: Senchuan Song, Zhiyong Chen, Shaoxue Li, Yanmin Huang, Yiqian Wan, Huacan Song
Format: Article
Language:English
Published: MDPI AG 2013-12-01
Series:Molecules
Subjects:
N13-substituted evodiamine derivatives
antitumor activity
apoptosis
solubility
Online Access:http://www.mdpi.com/1420-3049/18/12/15750
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spelling doaj-665dbf14faf24f24b87c34e7dd05d8592020-11-25T00:21:37ZengMDPI AGMolecules1420-30492013-12-011812157501576810.3390/molecules181215750molecules181215750Design, Synthesis and Evaluation of N13-Substituted Evodiamine Derivatives against Human Cancer Cell LinesSenchuan Song0Zhiyong Chen1Shaoxue Li2Yanmin Huang3Yiqian Wan4Huacan Song5School of Chemistry and Chemical Engineering, Sun Yat-sen University, Guangzhou 510275, ChinaSchool of Chemistry and Chemical Engineering, Sun Yat-sen University, Guangzhou 510275, ChinaSchool of Chemistry and Chemical Engineering, Sun Yat-sen University, Guangzhou 510275, ChinaCollege of Chemistry and Life Science, Guangxi Teachers Education University, Nanning 530001, ChinaSchool of Chemistry and Chemical Engineering, Sun Yat-sen University, Guangzhou 510275, ChinaSchool of Chemistry and Chemical Engineering, Sun Yat-sen University, Guangzhou 510275, ChinaAttempting 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.http://www.mdpi.com/1420-3049/18/12/15750N13-substituted evodiamine derivativesantitumor activityapoptosissolubility
collection DOAJ
language English
format Article
sources DOAJ
author Senchuan Song
Zhiyong Chen
Shaoxue Li
Yanmin Huang
Yiqian Wan
Huacan Song
spellingShingle Senchuan Song
Zhiyong Chen
Shaoxue Li
Yanmin Huang
Yiqian Wan
Huacan Song
Design, Synthesis and Evaluation of N13-Substituted Evodiamine Derivatives against Human Cancer Cell Lines
Molecules
N13-substituted evodiamine derivatives
antitumor activity
apoptosis
solubility
author_facet Senchuan Song
Zhiyong Chen
Shaoxue Li
Yanmin Huang
Yiqian Wan
Huacan Song
author_sort Senchuan Song
title 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_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_sort design, synthesis and evaluation of n13-substituted evodiamine derivatives against human cancer cell lines
publisher MDPI AG
series Molecules
issn 1420-3049
publishDate 2013-12-01
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 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.
topic N13-substituted evodiamine derivatives
antitumor activity
apoptosis
solubility
url http://www.mdpi.com/1420-3049/18/12/15750
work_keys_str_mv AT senchuansong designsynthesisandevaluationofn13substitutedevodiaminederivativesagainsthumancancercelllines
AT zhiyongchen designsynthesisandevaluationofn13substitutedevodiaminederivativesagainsthumancancercelllines
AT shaoxueli designsynthesisandevaluationofn13substitutedevodiaminederivativesagainsthumancancercelllines
AT yanminhuang designsynthesisandevaluationofn13substitutedevodiaminederivativesagainsthumancancercelllines
AT yiqianwan designsynthesisandevaluationofn13substitutedevodiaminederivativesagainsthumancancercelllines
AT huacansong designsynthesisandevaluationofn13substitutedevodiaminederivativesagainsthumancancercelllines
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