Copper(II) complexes of salicylaldehydes and 2-hydroxyphenones: synthesis, structure, thermal decomposition study and interaction with calf-thymus DNA and albumins

被引:41
作者
Zianna, Ariadni [1 ]
Psomas, George [1 ]
Hatzidimitriou, Antonios [1 ]
Lalia-Kantouri, Maria [1 ]
机构
[1] Aristotle Univ Thessaloniki, Fac Chem, Dept Gen & Inorgan Chem, GR-54124 Thessaloniki, Greece
关键词
NONSTEROIDAL ANTIINFLAMMATORY DRUGS; MONONUCLEAR METAL-COMPLEXES; PROTEIN-BINDING; BENZOPHENONE DERIVATIVES; CRYSTAL-STRUCTURE; FARNESYLTRANSFERASE INHIBITORS; SOLVENT-EXTRACTION; ZINC-COMPLEXES; SERUM-ALBUMIN; OXICAM NSAIDS;
D O I
10.1039/c4ra16484a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The neutral mononuclear copper(II) complexes with substituted salicylaldehyde (X-saloH), or 2-hydroxyphenone (ketoH) ligands, having the formula [Cu(L)(2)(S)(n)] (where S = solvent CH3OH or H2O and n = 0, 1 or 2) have been prepared and characterized, and their interaction with DNA and albumins was studied. The ligands are chelated to the metal ion through the phenolate and carbonyl oxygen atoms. The crystal structures of [Cu(5-NO2-salo)(2)(CH3OH)(2)] (3), [Cu(5-Cl-salo)(2)] (4), [Cu(bpo)(2)] (6) and [Cu(mpo)(2)]center dot 2H(2)O (7 center dot 2H(2)O) have been determined by X-ray crystallography. The thermal stability of the copper complexes has been investigated by a simultaneous TG/DTG-DTA technique. Spectroscopic (UV), electrochemical (cyclic voltammetry) and physicochemical (viscosity measurements) techniques have been employed in order to study the binding mode and strength of the complexes to calf-thymus (CT) DNA while competitive studies with ethidium bromide (EB) performed by fluorescence spectroscopy have revealed the ability of the complexes to displace the DNA-bound EB. In conclusion intercalation is the most possible mode of interaction of the complexes with CT DNA. The interaction of the complexes with serum albumin proteins has been studied by fluorescence emission spectroscopy and the determined binding constants exhibit relatively high values.
引用
收藏
页码:37495 / 37511
页数:17
相关论文
共 96 条
[1]  
[Anonymous], 2006, APEX VERS 2 US MAN M
[2]  
[Anonymous], 2008, PLANTA MED
[3]   CRYSTALS version 12: software for guided crystal structure analysis [J].
Betteridge, PW ;
Carruthers, JR ;
Cooper, RI ;
Prout, K ;
Watkin, DJ .
JOURNAL OF APPLIED CRYSTALLOGRAPHY, 2003, 36 :1487-1487
[4]   VOLTAMMETRIC STUDIES OF THE INTERACTION OF METAL-CHELATES WITH DNA .2. TRIS-CHELATED COMPLEXES OF COBALT(III) AND IRON(II) WITH 1,10-PHENANTHROLINE AND 2,2'-BIPYRIDINE [J].
CARTER, MT ;
RODRIGUEZ, M ;
BARD, AJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (24) :8901-8911
[5]   Spectroscopic studies of the binding of Cu(II) complexes of oxicam NSAIDs to alternating G-C and homopolymeric G-C sequences [J].
Chakraborty, Sreeja ;
Bose, Madhuparna ;
Sarkar, Munna .
SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2014, 122 :690-697
[6]   Benzophenone Derivatives from the Fruits of Garcinia multiflora and Their Anti-inflammatory Activity [J].
Chen, Jih-Jung ;
Ting, Chia-Wei ;
Hwang, Tsong-Long ;
Chen, Ih-Sheng .
JOURNAL OF NATURAL PRODUCTS, 2009, 72 (02) :253-258
[7]   Mononuclear metal complexes with Piroxicam:: Synthesis, structure and biological activity [J].
Christofis, P ;
Katsarou, M ;
Papakyriakou, A ;
Sanakis, Y ;
Katsaros, N ;
Psomas, G .
JOURNAL OF INORGANIC BIOCHEMISTRY, 2005, 99 (11) :2197-2210
[8]   Structures of nitrato-(2-hydroxybenzaldehydo) (2,2′-bipyridyl)copper and nitrato-(2-hydroxy-5-nitrobenzaldehydo)(2,2′-bipyridyl)copper [J].
Chumakov, Yu. M. ;
Paladi, L. G. ;
Antosyak, B. Ya. ;
Simonov, Yu. A. ;
Tsapkov, V. I. ;
Bocelli, G. ;
Gulea, A. P. ;
Ginju, D. ;
Palomares-Sanchez, S. A. .
CRYSTALLOGRAPHY REPORTS, 2011, 56 (02) :260-264
[9]   Unusual coordinating behavior by three non-steroidal anti-inflammatory drugs from the oxicam family towards copper(II). Synthesis, X-ray structure for copper(II)-isoxicam, -meloxicam and -cinnoxicam-derivative complexes, and cytotoxic activity for a copper(II)-piroxicam complex [J].
Cini, Renzo ;
Tamasi, Gabriella ;
Defazio, Sandra ;
Hursthouse, Michael B. .
JOURNAL OF INORGANIC BIOCHEMISTRY, 2007, 101 (08) :1140-1152
[10]   Copper-related diseases: From chemistry to molecular pathology [J].
Crisponi, Guido ;
Nurchi, Valeria Marina ;
Fanni, Daniela ;
Gerosa, Clara ;
Nemolato, Sonia ;
Faa, Gavino .
COORDINATION CHEMISTRY REVIEWS, 2010, 254 (7-8) :876-889