Electrochemical and spectroscopic investigations of carboxylic acid ligand and its triorganotin complexes for their binding with ds.DNA: In vitro biological studies

被引:37
作者
Arshad, Nasima [1 ]
Farooqi, Shahid Iqbal [1 ]
Bhatti, Moazzam H. [1 ]
Saleem, Samreen [2 ]
Mirza, Bushra [2 ]
机构
[1] Allama Iqbal Open Univ, Dept Chem, Islamabad, Pakistan
[2] Quaid I Azam Univ, Dept Biochem, Islamabad, Pakistan
关键词
Triorganotin(IV) carboxylates; UV-visible/fluorescence spectroscopy; Cyclic voltammerty; Intercalation; Binding constant/site size; Bioactivities; TRANSFER FLUORESCENCE PROBE; DNA-BINDING; ANTITUMOR ACTIVITIES; ORGANOTIN COMPOUNDS; CRYSTAL-STRUCTURE; METAL-COMPLEXES; SERUM-ALBUMIN; DERIVATIVES; DRUG; DIORGANOTIN(IV);
D O I
10.1016/j.jphotobiol.2013.05.005
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
A carboxylic acid ligand, (Z)-4-(4-acelylphenylamino)-4-oxobut-2-enoic acid (APA-1), and its triphenyl(APA-2) and tributyl-tin(IV) (APA-3) compounds have been synthesized and investigated for their binding with ds.DNA using UV-visible spectroscopy, fluorescence spectroscopy, cyclic voltammetry, and viscosity measurements under physiological conditions of pH and temperature. The experimental results from all techniques i.e. binding constant (K-b), binding site size (n) and free energy change (Delta G) were in good agreement and inferred spontaneous compound-DNA complexes formation via intercalation. Among all the compounds APA-3 showed comparatively greater binding at pH 4.7 as evident from its greater K-b values {APA-3: K-b: 5.63 x 10(4) M-1 (UV); 7.94 x .10(4) M-1 (fluorescence); 9.91 x 10(4) M-1 (CV)}. Electrochemical processes of compounds before and after the addition of DNA were found diffusion controlled. Among all compounds, APA-3 exhibited best antitumor activity. (C) 2013 Elsevier B.V. All rights reserved.
引用
收藏
页码:70 / 82
页数:13
相关论文
共 51 条
[1]   Di- and Triorganotin(IV) esters of 3,4-methylenedioxyphenylpropenoic acid: Synthesis, spectroscopic characterization and biological screening for antimicrobial, cytotoxic and antitumor activities [J].
Ahmad, Muhammad Sheeraz ;
Hussain, Mukhtiar ;
Hanif, Muhammad ;
Ali, Saqib ;
Qayyum, Mazhar ;
Mirza, Bushra .
CHEMICAL BIOLOGY & DRUG DESIGN, 2008, 71 (06) :568-576
[2]   Organometallic compounds in oncology: implications of novel organotins as antitumor agents [J].
Alama, Angela ;
Tasso, Bruno ;
Novelli, Federica ;
Sparatore, Fabio .
DRUG DISCOVERY TODAY, 2009, 14 (9-10) :500-508
[3]  
[Anonymous], 2001, Bioassay Techniques for Drug Development
[4]  
[Anonymous], 2001, ELECTROCHEMICAL METH
[5]   Enantiomeric Specificity of Biologically Significant Cu(II) and Zn(II) Chromone Complexes Towards DNA [J].
Arjmand, Farukh ;
Jamsheera, A. ;
Afzal, Mohd ;
Tabassum, Sartaj .
CHIRALITY, 2012, 24 (12) :977-986
[6]   Synthesis, crystal structure, DNA binding and in vitro biological studies of Ni(II), Cu(II) and Zn(II) complexes of N-phthaloylglycine [J].
Arshad, Nasima ;
Abbas, Naeem ;
Bhatti, Moazzam H. ;
Rashid, Naghmana ;
Tahir, Muhammad Nawaz ;
Saleem, Samreen ;
Mirza, Bushra .
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY B-BIOLOGY, 2012, 117 :228-239
[7]   Electrochemical and spectroscopic investigations of isoniazide and its analogs with ds.DNA at physiological pH: Evaluation of biological activities [J].
Arshad, Nasima ;
Yunus, Uzma ;
Razzque, Shumaila ;
Khan, Maliha ;
Saleem, Samreen ;
Mirza, Bushra ;
Rashid, Naghmana .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2012, 47 :452-461
[8]   Voltammetric measurements of the interaction of metal complexes with nucleic acids [J].
Aslanoglu, M ;
Isaac, CJ ;
Houlton, A ;
Horrocks, BR .
ANALYST, 2000, 125 (10) :1791-1798
[9]   Electrochemical and spectroscopic studies of the interaction of proflavine with DNA [J].
Aslanoglu, M .
ANALYTICAL SCIENCES, 2006, 22 (03) :439-443
[10]   Complexing of heavy metals with DNA and new bioaffinity method of their determination based on amperometric DNA-based biosensor [J].
Babkina, SS ;
Ulakhovich, NA .
ANALYTICAL CHEMISTRY, 2005, 77 (17) :5678-5685