Design, synthesis, and anti-tumor activities of novel triphenylethylene-coumarin hybrids, and their interactions with Ct-DNA

被引：66

作者：

Chen, Hua ^{[1
]}

Li, Shuai ^{[1
]}

Yao, Yuchao ^{[1
]}

Zhou, Likai ^{[1
]}

Zhao, Jianpeng ^{[1
]}

Gu, Yunjing ^{[1
]}

Wang, Kerang ^{[1
]}

Li, Xiaoliu ^{[1
]}

机构：

[1] Hebei Univ, Coll Chem & Environm Sci, Key Lab Chem Biol Hebei Prov, Baoding 071002, Peoples R China

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2013年 / 23卷 / 17期

基金：

中国国家自然科学基金;

关键词：

Coumarin; Triphenylethylene; Anti-tumor activities; DNA binding property; BINDING; DERIVATIVES; INHIBITORS; DOCKING;

D O I：

10.1016/j.bmcl.2013.07.009

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Novel triphenylethylene-coumarin hybrid derivatives containing different amounts of amino side chains Were designed and synthesized in good yields under microwave radiation. The derivatives 5b-d which possessed two amino side chains (except morpholinyl) showed a broad-spectrum and good anti-proliferative activity against five tumor cells and low cytotoxicity in osteoblast. UV-vis, fluorescence, and circular dichroism (CD) spectroscopies and thermal denaturation exhibited that compounds 10c, 5c, and 13c bearing amino side chain (except morpholinyl) on 4-phenyl had significant interactions with Ct-DNA by the intercalative mode of binding. Structure-activity relationships (SARs) analysis suggested that the amino alkyl chain would play an important role both in the compounds against tumor cells proliferation and their interactions with DNA. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：4785 / 4789

页数：5

共 36 条

[11] A hydrophilic three side-chained triazatruxene as a new strong and selective G-quadruplex ligand [J].

Ginnari-Satriani, Luca ;

Casagrande, Valentina ;

Bianco, Armandodoriano ;

Ortaggi, Giancarlo ;

Franceschin, Marco .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (12) :2513-2516

[12] Targeting Human Gastrointestinal Stromal Tumor Cells with a Quadruplex-Binding Small Molecule [J].

Gunaratnam, Mekala ;

Swank, Stephen ;

Haider, Shozeb M. ;

Galesa, Katja ;

Reszka, Anthony P. ;

Beltran, Monica ;

Cuenca, Francisco ;

Fletcher, Jonathan A. ;

Neidle, Stephen .

JOURNAL OF MEDICINAL CHEMISTRY, 2009, 52 (12) :3774-3783

[13] Synthesis and cytotoxic activity of benzopyran-based platinum(II) complexes [J].

Gupta, Atul ;

Mandal, Sanat K. ;

Leblanc, Valerie ;

Descoteaux, Caroline ;

Asselin, Eric ;

Berube, Gervais .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (14) :3982-3987

[14] Spectrometric and voltammetric investigation of interaction of neutral red with calf thymus DNA: pH effect [J].

Jiang, X ;

Shang, L ;

Wang, ZX ;

Dong, SJ .

BIOPHYSICAL CHEMISTRY, 2005, 118 (01) :42-50

[15] Biomedicine - Defining the "S" in SERMs [J].

Katzenellenbogen, BS ;

Katzenellenbogen, JA .

SCIENCE, 2002, 295 (5564) :2380-2381

[16] Targeting the Heat Shock Protein 90 Dimer with Dimeric Inhibitors [J].

Kusuma, Bhaskar Reddy ;

Peterson, Laura B. ;

Zhao, Huiping ;

Vielhauer, George ;

Holzbeierlein, Jeffrey ;

Blagg, Brian S. J. .

JOURNAL OF MEDICINAL CHEMISTRY, 2011, 54 (18) :6234-6253

[17]

Lin X, 2000, Curr Opin Drug Discov Devel, V3, P383

[18] Synthesis and molecular docking study of novel coumarin derivatives containing 4,5-dihydropyrazole moiety as potential antitumor agents [J].

Liu, Xin-Hua ;

Liu, Hui-Feng ;

Chen, Jin ;

Yang, Yang ;

Song, Bao-An ;

Bai, Lin-Shan ;

Liu, Jing-Xin ;

Zhu, Hai-Liang ;

Qi, Xing-Bao .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (19) :5705-5708

[19] ON DEMONSTRATING DNA INTERCALATION [J].

LONG, EC ;

BARTON, JK .

ACCOUNTS OF CHEMICAL RESEARCH, 1990, 23 (09) :271-273

[20] DNA binding and cleavage activity of [Ru(NH3)4(diimine)]Cl2 complexes [J].

Maheswari, PU ;

Palaniandavar, M .

INORGANICA CHIMICA ACTA, 2004, 357 (04) :901-912

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