Influence of carboxylic acid functionalities in ruthenium (II) polypyridyl complexes on DNA binding, cytotoxicity and antioxidant activity: Synthesis, structure and in vitro anticancer activity

被引:49
作者
Kamatchi, Thangavel Sathiya [1 ]
Chitrapriya, Nataraj [2 ]
Kim, Seog K. [2 ]
Fronczek, Frank R. [3 ]
Natarajan, Karuppannan [1 ]
机构
[1] Bharathiar Univ, Dept Chem, Coimbatore 641046, Tamil Nadu, India
[2] Yeungnam Univ, Dept Chem, Gyeongsan City 712749, Gyeong Buk, South Korea
[3] Louisiana State Univ, Dept Chem, Baton Rouge, LA 70803 USA
关键词
Ruthenium; Bipyridine; Dicarboxylic acid; DNA interaction; Cytotoxicity; Antioxidant activity; TRANSCRIPTION INHIBITION; DEOXYRIBONUCLEIC-ACID; LIGANDS; MODE; INTERCALATION; REDOX; CHEMISTRY; MEDICINE; AFFINITY; DESIGN;
D O I
10.1016/j.ejmech.2012.11.024
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Four new Ru(II) complexes [RuHCl(bpy)(PPh3)(CO)] (1), [RuHCl(bpy)(AsPh3)(CO)] (2) (bpy = 2,2'-bipyridine), [RuCl(HL)(PPh3)(2)(CO)] (3) and [RuCl(HL)(AsPh3)(2)(CO)] (4) (HL = 2,2'-bipyridine-4,4'-dicarboxylic acid) were synthesized and characterized. X-ray diffraction was used to characterize 3 in solid state. The interactions of these complexes with DNA were explored by different techniques which revealed that the complexes could bind to CT-DNA through non-intercalation. The in vitro cytotoxic and antioxidant activities of the complexes validated against a panel of cancer cell lines and free radicals showed that 3 and 4 possess quite high anticancer and antioxidant activities over 1, 2 and standard drugs. An apparent dependence of biological activities on incorporation of COOH in bipyridine moiety was noticed: Inclusion of COOH caused significant differences in DNA binding, cytotoxicity and antioxidant activity. (C) 2012 Elsevier Masson SAS. All rights reserved.
引用
收藏
页码:253 / 264
页数:12
相关论文
共 50 条
[11]   Synthesis, characterization; DNA binding and antitumor activity of ruthenium(II) polypyridyl complexes [J].
Srishailam, A. ;
Gabra, Nazar Mohammed ;
Kumar, Yata Praveen ;
Reddy, Kotha Laxma ;
Devi, C. Shobha ;
Kumar, D. Anil ;
Singh, Surya S. ;
Satyanarayana, S. .
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY B-BIOLOGY, 2014, 141 :47-58
[12]   Synthesis, DNA-binding and topoisomerase inhibitory activity of ruthenium(II) polypyridyl complexes [J].
Du, Ke-Jie ;
Wang, Jin-Quan ;
Kou, Jun-Feng ;
Li, Guan-Ying ;
Wang, Li-Li ;
Chao, Hui ;
Ji, Liang-Nian .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2011, 46 (04) :1056-1065
[13]   Synthesis, Structure, DNA-Binding Properties, and Cytotoxicity of Ruthenium(II) Polypyridyl Complexes [J].
Liu, Yun-Jun ;
Zeng, Cheng-Hui ;
Yao, Jun-Hua ;
Wu, Fu-Hai ;
He, Li-Xin ;
Huang, Hong-Liang .
CHEMISTRY & BIODIVERSITY, 2010, 7 (07) :1770-1783
[14]   In Vitro Cytotoxicity, Apoptosis, DNA-Binding, and Antioxidant Activity Studies of Ruthenium (II) Complexes [J].
Huang, Hong-Liang ;
Liu, Yun-Jun ;
Zeng, Cheng-Hui ;
He, Li-Xin ;
Wu, Fu-Hai .
DNA AND CELL BIOLOGY, 2010, 29 (05) :261-270
[15]   Synthesis, Spectral Properties and DFT Calculations of new Ruthenium (II) Polypyridyl Complexes; DNA Binding Affinity and in Vitro Cytotoxicity Activity [J].
Mallepally, Rajender Reddy ;
Chintakuntla, Nagamani ;
Putta, Venkat Reddy ;
Nagasuryaprasad, K. ;
Vuradi, Ravi Kumar ;
Madhuri, P. ;
Singh, Satyanarayana S. ;
Chitumalla, Ramesh Kumar ;
Jang, Joonkyung ;
Penumaka, Nagababu ;
Sirasani, Satyanarayana .
JOURNAL OF FLUORESCENCE, 2017, 27 (04) :1513-1530
[16]   Synthesis, characterization, cytotoxicity, apoptotic inducing activity, cellular uptake, interaction of DNA binding and antioxidant activity studies of ruthenium(II) complexes [J].
Liu, Yun-Jun ;
Liang, Zhen-Hua ;
Hong, Xian-Lan ;
Li, Zheng-Zheng ;
Yao, Jun-Hua ;
Huang, Hong-Liang .
INORGANICA CHIMICA ACTA, 2012, 387 :117-124
[17]   Ruthenium(II) complexes: Cellular uptake, cytotoxicity, DNA-binding, photocleavage and antioxidant activity studies [J].
Li, Zheng-Zheng ;
Liang, Zhen-Hua ;
Huang, Hong-Liang ;
Liu, Yun-Jun .
JOURNAL OF MOLECULAR STRUCTURE, 2011, 1001 (1-3) :36-42
[18]   DNA binding, cytotoxicity, and apoptotic-inducing activity of ruthenium(II) polypyridyl complex [J].
Zhang, Peng ;
Chen, Jie ;
Liang, Yi .
ACTA BIOCHIMICA ET BIOPHYSICA SINICA, 2010, 42 (07) :440-449
[19]   DNA-binding and cleavage activity of polypyridyl ruthenium(II) complexes [J].
Patel, Mohan N. ;
Gandhi, Deepen S. ;
Parmar, Pradhuman A. ;
Joshi, Hardik N. .
JOURNAL OF COORDINATION CHEMISTRY, 2012, 65 (11) :1926-1936
[20]   SYNTHESIS, CHARACTERIZATION, CELLULAR UPTAKE, APOPTOSIS, CYTOTOXICITY, DNA-BINDING, AND ANTIOXIDANT ACTIVITY STUDIES OF RUTHENIUM(II) COMPLEXES [J].
Xu, Li ;
Zhong, Nan-Jing ;
Huang, Hong-Liang ;
Liang, Zhen-Hua ;
Li, Zheng-Zheng ;
Liu, Yun-Jun .
NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2012, 31 (08) :575-591