Design, synthesis and evaluation of N13-substituted evodiamine derivatives against human cancer cell lines

Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry
Senchuan SongHuacan Song

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.

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Citations

Dec 17, 2017·The Journal of Pharmacology and Experimental Therapeutics·Jamie R FriedmanPiyali Dasgupta
Oct 2, 2019·Organic & Biomolecular Chemistry·Yiting SuHaijun Chen
Apr 2, 2019·Current Topics in Medicinal Chemistry·Benjamin Diethelm-VarelaFengtian Xue
Nov 2, 2018·International Journal of Molecular Sciences·Xu HuFanxing Xu

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Methods Mentioned

BETA
flow cytometry
column chromatography

Software Mentioned

[UNK]
ChemBioDraw Ultra

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