Unprecedented synthesis, in vitro and in vivo anti-cancer evaluation of novel triazolonaphthalimide derivatives

被引:13
|
作者
Li, Shasha [1 ]
Zhong, Wenhe [1 ]
Li, Zhongjun [1 ]
Meng, Xiangbao [1 ]
机构
[1] Peking Univ, Sch Pharmaceut Sci, Dept Biol Chem, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China
关键词
Naphthalimide; Triazole; N-oxide; DNA intercalator; Anti-cancer; HETEROCYCLIC FUSED NAPHTHALIMIDES; BENZYNE CLICK CHEMISTRY; COMBI-TARGETING CONCEPT; AMINOALKYL SIDE-CHAINS; DNA-BINDING PROPERTIES; BIOLOGICAL EVALUATION; ANTITUMOR-ACTIVITY; BENZOTRIAZOLE DERIVATIVES; SOLID TUMOR; N-OXIDE;
D O I
10.1016/j.ejmech.2011.11.025
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
An efficient synthesis method for fusing triazole ring onto the naphthalimide core was described. The anti-cancer activities of the generated triazolonaphthalimide derivatives were evaluated with five cancer cell lines. The compounds generally displayed higher potency than amonafide. 4d,4e carrying two amino side chains showed the strongest cytotoxicities. N-oxide 5, a prodrug of 4a, was designed and synthesized. The agent was expected to be activated under the hypoxic condition in tumor tissue. Compared with 4a, 5 manifested much lower cytotoxicity both in cancer cell lines and human normal cells in the in vitro assays. However, N-oxide 5 performed potent anti-cancer activity in vivo using S-180 sarcoma bearing mice. All the results suggested that 5 was a promising anti-cancer agent. (C) 2011 Elsevier Masson SAS. All rights reserved.
引用
收藏
页码:546 / 552
页数:7
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