The antitumor activity of zinc(II) and copper(II) complexes with 5,7-dihalo-substituted-8-quinolinoline

被引：101
作者：
Liu, Yan-Cheng [1 ]
Wei, Jian-Hua [1 ]
Chen, Zhen-Feng [1 ]
Liu, Mei [1 ]
Gu, Yun-Qiong [1 ]
Huang, Ke-Bin [1 ]
Li, Zhu-Quan [1 ]
Liang, Hong [1 ]
机构：
[1] Guangxi Normal Univ, Sch Pharm & Chem, State Key Lab Cultivat Base Chem & Mol Engn Med R, Guilin 541004, Peoples R China
来源：
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY | 2013年 / 69卷
关键词：
5,7-Dihalo-substituted-8-quinolinoline; Zn(II) complex; Cu(II) complex; Crystal structure; Cytotoxicity; DNA binding; CRYSTAL-STRUCTURE; DNA INTERACTION; IN-VITRO; CYTOTOXICITY; BINDING; 8-HYDROXYQUINOLINE; INTERCALATION; ZN(II); DYE;
D O I：
10.1016/j.ejmech.2013.08.033
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
[Zn-2(CIQ)(4)(CH3OH)(2)] (I), [Zn(BrQ)(2)(H2O)(2)] (2), [Zn-2(CIIQ](4)] (3) and [Cu(BrQ)(2)] (4) (H-ClQ = 5,7-dichloro8-hydroxylquinoline, H-BrQ = 5,7-dibromo-8-hydroxylquinoline, and H-CIIQ = 5-chloro-7-iodo-8hydroxylquinoline) were synthesized. Compounds 1-4 showed high anti-proliferative cytotoxicities against BEL-7404, SK-OV-3, NCI-H460 tumor cells, and HL-7702 normal cells in vitro, with IC50 values in the 1.4 nM to 32.13 mu M range. Compounds 2-4 exhibited significantly enhanced cytotoxicity against BEL7404 cell line, comparing with free 5,7-dihalo-8-quinolinol. Western blotting analysis showed that 2, 3 depleted mutant p53 protein in MDA-MB-231, and compound 2 decreased the ratio of Bc1-2/Bax in NCIH460 significantly. The binding abilities of 1-4 to DNA were stronger than that of free quinolinol ligand. Intercalation is the probable binding mode for the complexes and free quinolinol ligands with DNA. (C) 2013 Elsevier Masson SAS. All rights reserved.
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页码：554 / 563
页数：10
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