title: Design, synthesis and evaluation of N13-substituted evodiamine derivatives against human cancer cell lines.
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.
authors.forename: Senchuan
authors.initials: S
authors.lastname: Song
authors.forename: Zhiyong
authors.initials: Z
authors.lastname: Chen
authors.forename: Shaoxue
authors.initials: S
authors.lastname: Li
authors.forename: Yanmin
authors.initials: Y
authors.lastname: Huang
authors.affiliation: School of Chemistry and Chemical Engineering, Sun Yat-sen University, Guangzhou 510275, China. yjhxhc@mail.sysu.edu.cn.
authors.forename: Yiqian
authors.initials: Y
authors.lastname: Wan
authors.affiliation: School of Chemistry and Chemical Engineering, Sun Yat-sen University, Guangzhou 510275, China. ceswyq@mail.sysu.edu.cn.
authors.forename: Huacan
authors.initials: H
authors.lastname: Song
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D017209:Apoptosis / Q000187:drug effects; D045744:Cell Line, Tumor; D006801:Humans; D061986:MCF-7 Cells; D008958:Models, Molecular; D008968:Molecular Conformation; D011799:Quinazolines / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*
chemical_list: D000970:Antineoplastic Agents; D011799:Quinazolines; C049639:evodiamine