Synthesis, characterization and in vitro DNA binding and cleavage studies of Cu(II)/Zn(II) dipeptide complexes

被引:65
作者
Arjmand, Farukh [1 ]
Jamsheera, A. [1 ]
Mohapatra, D. K. [2 ]
机构
[1] Aligarh Muslim Univ, Dept Chem, Aligarh 202002, Uttar Pradesh, India
[2] Indian Inst Chem Technol, Div Oriented Synth Lab, Hyderabad 500607, Andhra Pradesh, India
关键词
Dipeptide Cu(II) and Zn(II) complexes; DNA binding profile; pBR322 DNA cleavage; In vitro anticancer activity; RAY CRYSTAL-STRUCTURE; COPPER(II) COMPLEXES; SEQUENCE SELECTIVITY; HYDROLYTIC CLEAVAGE; CELL LINES; PEPTIDE; METALLOPEPTIDES; RUTHENIUM(II); PHOTOCLEAVAGE; CYTOTOXICITY;
D O I
10.1016/j.jphotobiol.2012.12.009
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
Novel dipeptide complexes Cu(II)center dot Val-Pro (1), Zn(II)center dot Val-Pro (2), Cu(II)center dot Ala-Pro (3) and Zn(II)center dot Ala-Pro (4) were synthesized and thoroughly characterized using different spectroscopic techniques including elemental analyses, IR, NMR, ESI-MS and molar conductance measurements. The solution stability study carried out by UV-vis absorption titration over a broad range of pH proved the stability of the complexes in solution. In vitro DNA binding studies of complexes 1-4 carried out employing absorption, fluorescence, circular dichroism and viscometric studies revealed the binding of complexes to DNA via groove binding. UV-vis titrations of 1-4 with mononucleotides of interest viz., 5'-GMP and 5'-TMP were also carried out. The DNA cleavage activity of the complexes I and 2 were ascertained by gel electrophoresis assay which revealed that the complexes are good DNA cleavage agents and the cleavage mechanism involved a hydrolytic pathway. Furthermore, in vitro antitumor activity of complex 1 was screened against human cancer cell lines of different histological origin. (C) 2013 Elsevier B.V. All rights reserved.
引用
收藏
页码:75 / 85
页数:11
相关论文
共 49 条
[1]   Synthesis, characterization and stability constant determination of L-phenylalanine ternary complexes of cobalt(II), nickel(II), copper(II) with N-heterocyclic aromatic bases and X-ray crystal structure of aqua-1,10-phenanthroline-L-phenylalaninatocopper(II) perchlorate complex [J].
AbdelRahman, LH ;
Battaglia, LP .
POLYHEDRON, 1996, 15 (02) :327-334
[2]  
[Anonymous], 2002, SMALL MOL DNA RNA BI
[3]   Highly selective recognition of thymidine mono- and diphosphate nucleotides in aqueous solution by ditopic receptors zinc(II)-bis(cyclen) complexes (cyclen 1,4,7,10-tetraazacyclododecane) [J].
Aoki, S ;
Kimura, E .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (19) :4542-4548
[4]   Synthesis, characterization of Cu(II) and Zn(II) complexes of proline-glycine and proline-leucine tetrapeptides: In vitro DNA binding and cleavage studies [J].
Arjmand, Farukh ;
Parveen, Shazia ;
Mohapatra, D. K. .
INORGANICA CHIMICA ACTA, 2012, 388 :1-10
[5]   Synthesis, characterization and in vitro DNA binding studies of tin(IV) complexes of tert-butyl 1-(2-hydroxy-1-phenylethylamino)-3-methyl-1-oxobutan-2-yl carbamate [J].
Arjmand, Farukh ;
Jamsheera, A. .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2011, 696 (22) :3572-3579
[6]   Theoretical study of cisplatin binding to purine bases: Why does cisplatin prefer guanine over adenine? [J].
Baik, MH ;
Friesner, RA ;
Lippard, SJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (46) :14082-14092
[7]   Sequence-specific DNA binding by noncovalent peptide-tripyrrole conjugates [J].
Blanco, Juan B. ;
Dodero, Veronica L. ;
Vazquez, M. Eugenio ;
Mosquera, Manuel ;
Castedo, Luis ;
Mascarenas, Jose L. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (48) :8210-8214
[8]  
Bodanszky A., 1984, PRACTICE PEPTIDE SYN, P1
[9]   Zinc-bound thiolate-disulfide exchange:: A strategy for inhibiting metallo-β-lactamases [J].
Boerzel, H ;
Koeckert, M ;
Bu, WM ;
Spingler, B ;
Lippard, SJ .
INORGANIC CHEMISTRY, 2003, 42 (05) :1604-1615
[10]   A simple, high-resolution method for establishing DNA binding affinity and sequence selectivity [J].
Boger, DL ;
Fink, BE ;
Brunette, SR ;
Tse, WC ;
Hedrick, MP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (25) :5878-5891