Synthesis, X-ray structures, properties and SOD-like activity of ternary copper(II) complexes showing the N4O2 coordination with a combination of monodentate and bidentate N-donor ligands

被引:6
作者
Klanicova, Alena [2 ]
Houck, Joseph D. [2 ]
Baran, Peter [2 ,3 ]
Travnicek, Zdenek [1 ,2 ]
机构
[1] Palacky Univ, Reg Ctr Adv Technol & Mat, CZ-77146 Olomouc, Czech Republic
[2] Palacky Univ, Dept Inorgan Chem, CZ-77146 Olomouc, Czech Republic
[3] Juniata Coll, Dept Chem, Huntingdon, PA 16652 USA
关键词
Copper(II) complex; Crystal structure; 6-(Benzylamino)purine; 1,10-Phenanthroline; SOD-like activity; NUCLEOTIDE BASE COMPLEXES; METAL-PURINE COMPLEXES; CRYSTAL-STRUCTURE; DNA-CLEAVAGE; INTERLIGAND INTERACTIONS; MOLECULAR-STRUCTURE; IN-VITRO; 6-BENZYLAMINOPURINE; DERIVATIVES; MONOHYDRATE;
D O I
10.1016/j.ica.2011.11.021
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A series of novel copper(II) complexes with the composition of [Cu(H2O)(2)(L1-5)(2)(phen)]center dot 2MeOH (1-5), where HL1 = 6-(2-fluorobenzylamino) purine, HL2 = 6-(3-fluorobenzylamino) purine, HL3 = 6-(4-fluorobenzylamino) purine, HL4 = 6-(2-chlorobenzylamino)purine, HL5 = 6-(3-chlorobenzylamino) purine, phen = 1,10-phenanthroline, was synthesized and characterized by elemental analysis, electronic and infrared spectroscopy, magnetic and conductivity measurements. Single-crystal X-ray analysis of complexes 1-4 showed the distorted octahedral geometry in the vicinity of the copper(II) atom, which is coordinated by four nitrogen atoms (two from the bidentate phen ligand and the other two from monodentate 6-(benzylamino) purine derivatives) and two oxygen atoms from the aqua ligands, which together form the N4O2 donor set. The antiradical activity of the prepared complexes was tested by an in vitro SOD-like assay. The IC50 values were found ranging between 104 and 146 mu M, which represents ca. 0.5% of the native bovine Cu, Zn-SOD effect. (C) 2011 Elsevier B. V. All rights reserved.
引用
收藏
页码:47 / 53
页数:7
相关论文
共 59 条
[1]   Metal-nucleobase interactions: Synthesis and crystal structure of trichlorobis(N-6-benzyl adeninium)copper(II) chloride dihydrate [J].
Balasubramanian, TP ;
Muthiah, PT ;
Ananthasaravanan ;
Mazumdar, SK .
JOURNAL OF INORGANIC BIOCHEMISTRY, 1996, 63 (03) :175-181
[2]   A redetermination of (N9-adenine-κN)aqua[glycylglycinato(2-)-κ3N,N′,O]copper(II) [J].
Brandi-Blanco, Maria Pilar ;
Dumet-Fernandes, Bruno ;
Gonzalez-Perez, Josefa Maria ;
Choquesillo-Lazarte, Duane .
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2007, 63 :M1598-U394
[3]   PREPARATION AND MAGNETIC AND STRUCTURAL EXAMINATION OF MONOMERIC, DIMERIC, AND POLYMERIC ADENINE COMPLEXES OF COPPER(II) [J].
BROWN, DB ;
HALL, JW ;
HELIS, HM ;
WALTON, EG ;
HODGSON, DJ ;
HATFIELD, WE .
INORGANIC CHEMISTRY, 1977, 16 (11) :2675-2680
[4]   Three new modes of adenine-copper(II) coordination:: interligand interactions controlling the selective N3-, N7- and bridging μ-N3,N7-metal-bonding of adenine to different N-substituted iminodiacetato-copper(II) chelates [J].
Bugella-Altamirano, E ;
Choquesillo-Lazarte, D ;
González-Pérez, JM ;
Sánchez-Moreno, MJ ;
Marín-Sánchez, R ;
Martín-Ramos, JD ;
Covelo, B ;
Carballo, R ;
Castiñeiras, A ;
Niclós-Gutiérrez, J .
INORGANICA CHIMICA ACTA, 2002, 339 :160-170
[5]   Structural (X-ray), spectral (FT-IR and Raman) and quantum chemical investigations of a series of 6-benzylaminopurine derivatives [J].
Cajan, Michal ;
Travnicek, Zdenek .
JOURNAL OF MOLECULAR STRUCTURE, 2011, 994 (1-3) :350-359
[6]  
Castineiras A., 2008, COMMUNICATION
[7]   Metal Complexes, their Cellular Targets and Potential for Cancer Therapy [J].
Chen, D. ;
Milacic, Vesna ;
Frezza, Michael ;
Dou, Q. Ping .
CURRENT PHARMACEUTICAL DESIGN, 2009, 15 (07) :777-791
[8]   Induction of apoptosis by a novel copper-based anticancer compound, casiopeina II, in L1210 murine leukaemia and CH1 human ovarian carcinoma cells [J].
De Vizcaya-Ruiz, A ;
Rivero-Muller, A ;
Ruiz-Ramirez, L ;
Kass, GEN ;
Kelland, LR ;
Orr, RM ;
Dobrota, M .
TOXICOLOGY IN VITRO, 2000, 14 (01) :1-5
[9]   CRYSTAL-STRUCTURE OF DIBROMODIADENINIUMCOPPER(II) DIBROMIDE - COMPLEX WITH UNIDENTATE ADENINE [J].
DEMEESTER, P ;
SKAPSKI, AC .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1973, (04) :424-427
[10]   Effects of dinuclear copper(II) complexes with 6-(benzylamino)purine derivatives on AhR and PXR dependent expression of cytochromes P450 CYP1A2 and CYP3A4 genes in primary cultures of human hepatocytes [J].
Dvorak, Zdenek ;
Vrzal, Radim ;
Starha, Pavel ;
Klanicova, Alena ;
Travnicek, Zdenek .
TOXICOLOGY IN VITRO, 2010, 24 (02) :425-429