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
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
收藏
页码:4785 / 4789
页数:5
相关论文
共 36 条
[21]   Lead identification of a potent benzopyranone selective estrogen receptor modulator [J].
McKie, JA ;
Bhagwat, SS ;
Brady, H ;
Doubleday, M ;
Gayo, L ;
Hickman, M ;
Jalluri, RK ;
Khammungkhune, S ;
Kois, A ;
Mortensen, D ;
Richard, N ;
Sapienza, J ;
Shevlin, G ;
Stein, B ;
Sutherland, M .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (13) :3407-3410
[22]   Hybrid molecules with a dual mode of action: Dream or reality? [J].
Meunier, Bernard .
ACCOUNTS OF CHEMICAL RESEARCH, 2008, 41 (01) :69-77
[23]   O2 quenching of ruthenium(II) tris(2,2′-bypyridyl)2+ within the water pool of perfluoropolyether-based reverse micelles formed in supercritical carbon dioxide [J].
Pandey, S ;
Baker, GA ;
Kane, MA ;
Bonzagni, NJ ;
Bright, FV .
LANGMUIR, 2000, 16 (13) :5593-5599
[24]   INTERACTIONS OF PORPHYRINS WITH NUCLEIC-ACIDS [J].
PASTERNACK, RF ;
GIBBS, EJ ;
VILLAFRANCA, JJ .
BIOCHEMISTRY, 1983, 22 (10) :2406-2414
[25]   DNA cross-linking agents as antitumor drugs [J].
Rajski, SR ;
Williams, RM .
CHEMICAL REVIEWS, 1998, 98 (08) :2723-2795
[26]   Quest for Mode of Binding of 2-(4-(Dimethylamino)styryl)-1-methylpyridinium Iodide with Calf Thymus DNA [J].
Sahoo, Dibakar ;
Bhattacharya, Prosenjit ;
Chakravorti, Sankar .
JOURNAL OF PHYSICAL CHEMISTRY B, 2010, 114 (05) :2044-2050
[27]   Synthesis and in vitro evaluation of novel coumarin-chalcone hybrids as potential anticancer agents [J].
Sashidhara, Koneni V. ;
Kumar, Abdhesh ;
Kumar, Manoj ;
Sarkar, Jayanta ;
Sinha, Sudhir .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (24) :7205-7211
[28]   Hydroxycoumarin Derivatives: Novel and Potent α-Glucosidase Inhibitors [J].
Shen, Qiong ;
Shao, Jialiang ;
Peng, Quan ;
Zhang, Wanjin ;
Ma, Lin ;
Chan, Albert S. C. ;
Gu, Lianquan .
JOURNAL OF MEDICINAL CHEMISTRY, 2010, 53 (23) :8252-8259
[29]   Design, Synthesis, and Biological Evaluation of Imidazolyl Derivatives of 4,7-Disubstituted Coumarins as Aromatase Inhibitors Selective over 17-α-Hydroxylase/C17-20 Lyase [J].
Stefanachi, Angela ;
Favia, Angelo D. ;
Nicolotti, Orazio ;
Leonetti, Francesco ;
Pisani, Leonardo ;
Catto, Marco ;
Zimmer, Christina ;
Hartmann, Rolf W. ;
Carotti, Angelo .
JOURNAL OF MEDICINAL CHEMISTRY, 2011, 54 (06) :1613-1625
[30]   Synthesis and biological evaluation of 4-styrylcoumarin derivatives as inhibitors of TNF-α and IL-6 with anti-tubercular activity [J].
Upadhyay, Kuldip ;
Bavishi, Abhay ;
Thakrar, Shailesh ;
Radadiya, Ashish ;
Vala, Hardevsinh ;
Parekh, Shrey ;
Bhavsar, Dhairya ;
Savant, Mahesh ;
Parmar, Manisha ;
Adlakha, Priti ;
Shah, Anamik .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2011, 21 (08) :2547-2549