High antitumor activity of 5,7-dihalo-8-quinolinolato tin(IV) complexes

被引：34

作者：

Chen, Zhen-Feng ^{[1
]}

Peng, Yan ^{[1
]}

Gu, Yun-Qiong ^{[1
]}

Liu, Yan-Cheng ^{[1
]}

Liu, Mei ^{[1
]}

Huang, Ke-Bin ^{[1
]}

Hu, Kun ^{[1
]}

Liang, Hong ^{[1
]}

机构：

[1] Guangxi Normal Univ, Sch Chem & Chem Engn, State Key Lab Cultivat Base Chem & Mol Engn Med R, Guilin 541004, Peoples R China

来源：

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY | 2013年 / 62卷

关键词：

5,7-dihalo-8-quinolinol tin(IV) complex; Crystal structure; Cytotoxicity; DNA binding; IN-VITRO; DNA-BINDING; ALZHEIMERS-DISEASE; CRYSTAL-STRUCTURE; INTERCALATION; RUTHENIUM(II); CYTOTOXICITY; CLIOQUINOL; PROTEASOME; CONJUGATE;

D O I：

10.1016/j.ejmech.2012.12.030

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Three tin(IV) complexes [Sn(ClQ)(2)Cl-2] (1), [Sn(BrQ)(2)Cl-2] (2) and [Sn(ClIQ)(2)Cl-2] (3) were prepared (HClQ = 5,7-dichloro-8-hydroxylquinoline, H-BrQ = 5,7-dibromo-8-hydroxylquinoline, H-ClIQ = 5-chloro-7-iodo-8-hydroxylquinoline) and their in vitro cytotoxicities against BEL7404, SKOV-3, NCI-H460, HL-7702 cell lines were evaluated. The complexes showed high anti-proliferative activity toward the tested cell lines with IC50 values ranging from 20 nM to 5.11 mu M. Compared with 5,7-dihalo-8-quinolinol, most complexes exhibited significantly enhanced cytotoxicity (except 2 against SKOV-3 and NCI-H460). They also displayed some selective cytotoxicity favoring the tested tumor cells over the normal human liver HL-7702 cells. Compared with their quinolinol ligands, complexes 1-3 bind more strongly with DNA. Intercalation is the most probable binding mode for both the complexes and their quinolinol ligands. (C) 2012 Elsevier Masson SAS. All rights reserved.

引用

页码：51 / 58

页数：8

共 49 条

[1] NITROGEN DONOR CHELATES OF BIVALENT TIN CHLORIDE .2. THE CRYSTAL-STRUCTURES OF SNCL2.(2,2'-BIPYRIDYL) AND SNCL2.(1,10-PHENANTHROLINE) [J].

ARCHER, SJ ;

KOCH, KR ;

SCHMIDT, S .

INORGANICA CHIMICA ACTA, 1987, 126 (02) :209-218

[2] Structure and emission properties of Er3Q9 (Q=8-quinolinolate) [J].

Artizzu, F ;

Deplano, P ;

Marchiò, L ;

Mercuri, ML ;

Pilia, L ;

Serpe, A ;

Quochi, F ;

Orrú, R ;

Cordella, F ;

Meinardi, F ;

Tubino, R ;

Mura, A ;

Bongiovanni, G .

INORGANIC CHEMISTRY, 2005, 44 (04) :840-842

[3] Synthesis, structural characterization and biological studies of the triphenyltin(IV) complex with 2-thiobarbituric acid [J].

Balas, V. I. ;

Verginadis, I. I. ;

Geromichalos, G. D. ;

Kourkoumelis, N. ;

Male, L. ;

Hursthouse, M. B. ;

Repana, K. H. ;

Yiannaki, E. ;

Charalabopoulos, K. ;

Bakas, T. ;

Hadjikakou, S. K. .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2011, 46 (07) :2835-2844

[4] DNA minor groove binders as potential antitumor and antimicrobial agents [J].

Baraldi, PG ;

Bovero, A ;

Fruttarolo, F ;

Preti, D ;

Tabrizi, MA ;

Pavani, MG ;

Romagnoli, R .

MEDICINAL RESEARCH REVIEWS, 2004, 24 (04) :475-528

[5] VOLTAMMETRIC STUDIES OF THE INTERACTION OF METAL-CHELATES WITH DNA .2. TRIS-CHELATED COMPLEXES OF COBALT(III) AND IRON(II) WITH 1,10-PHENANTHROLINE AND 2,2'-BIPYRIDINE [J].

CARTER, MT ;

RODRIGUEZ, M ;

BARD, AJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (24) :8901-8911

[6] DNA binding studies of ruthenium(II) complexes containing asymmetric tridentate ligands [J].

Chao, H ;

Mei, WJ ;

Huang, QW ;

Ji, LN .

JOURNAL OF INORGANIC BIOCHEMISTRY, 2002, 92 (3-4) :165-170

[7] DNA binding studies of novel copper(II) complexes containing L-tryptophan as chiral auxiliary:: In vitro antitumor activity of Cu-Sn2 complex in human neuroblastoma cells [J].

Chauhan, Mala ;

Banerjee, Kakoli ;

Arjmand, Farukh .

INORGANIC CHEMISTRY, 2007, 46 (08) :3072-3082

[8] Clioquinol, a therapeutic agent for Alzheimer's disease, has proteasome-inhibitory, androgen receptor-suppressing, apoptosis-inducing, and antitumor activities in human prostate cancer cells and xenografts [J].

Chen, Di ;

Cui, Qiuzhi Cindy ;

Yang, Huanjie ;

Barrea, Raul A. ;

Sarkar, Fazlul H. ;

Sheng, Shijie ;

Yan, Bing ;

Reddy, G. Prem Veer ;

Dou, Q. Ping .

CANCER RESEARCH, 2007, 67 (04) :1636-1644

[9] Synthesis and pharmacological exploitation of clioquinol-derived copper-binding apoptosis inducers triggering reactive oxygen species generation and MAPK pathway activation [J].

Chen, Hui-Ling ;

Chang, Chun-Yi ;

Lee, Hsun-Tzu ;

Lin, Hua-Hsuan ;

Lu, Pei-Jung ;

Yang, Chia-Ning ;

Shiau, Chung-Wai ;

Shaw, Arthur Y. .

BIOORGANIC & MEDICINAL CHEMISTRY, 2009, 17 (20) :7239-7247

[10] TCM Active Ingredient Oxoglaucine Metal Complexes: Crystal Structure, Cytotoxicity, and Interaction with DNA [J].

Chen, Zhen-Feng ;

Shi, Yan-Fang ;

Liu, Yan-Cheng ;

Hong, Xue ;

Geng, Bo ;

Peng, Yan ;

Liang, Hong .

INORGANIC CHEMISTRY, 2012, 51 (04) :1998-2009

← 1 2 3 4 5 →