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
[11]   INHIBITION OF LANDSCHUTZ ASCITES TUMOUR GROWTH BY METAL CHELATES DERIVED FROM 3,4,7,8-TETRAMETHYL-1,10-PHENANTHROLINE [J].
DWYER, FP ;
MAYHEW, E ;
ROE, EMF ;
SHULMAN, A .
BRITISH JOURNAL OF CANCER, 1965, 19 (01) :195-&
[12]   Anti proliferative activity and QSAR study of copper(II) mixed chelate [Cu(N-N)(acetylacetonato)]NO3 and [Cu(N-N)(glycinato)]NO3 complexes, (Casiopeinas®) [J].
Elena Bravo-Gomez, Maria ;
Carlos Garcia-Ramos, Juan ;
Gracia-Mora, Isabel ;
Ruiz-Azuara, Lena .
JOURNAL OF INORGANIC BIOCHEMISTRY, 2009, 103 (02) :299-309
[13]   π-Stacking between Casiopeinas® and DNA bases [J].
Galindo-Murillo, Rodrigo ;
Hernandez-Lima, Joseelyne ;
Gonzalez-Rendon, Mayra ;
Cortes-Guzman, Fernando ;
Ruiz-Azuara, Lena ;
Moreno-Esparza, Rafael .
PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2011, 13 (32) :14510-14515
[14]   A dinuclear copper(II) complex with adeninate bridge ligands and prominent DNA cleavage activity.: Structural and spectroscopic characterization and magnetic properties [J].
Garcia-Gimenez, Jose Luis ;
Alzuet, Gloria ;
Gonzalez-Alvarez, Marta ;
Castineiras, Alfonso ;
Liu-Gonzalez, Malva ;
Borras, Joaquin .
INORGANIC CHEMISTRY, 2007, 46 (17) :7178-7188
[15]   Supramolecular architectures assembled by the interaction of purine nucleobases with metal-oxalato frameworks.: Non-covalent stabilization of the 7H-adenine tautomer in the solid-state [J].
García-Terán, JP ;
Castillo, O ;
Luque, A ;
García-Couceiro, U ;
Beobide, G ;
Román, P .
DALTON TRANSACTIONS, 2006, (07) :902-911
[17]   CRYSTAL-STRUCTURE OF A TETRANUCLEAR COPPER(II)-INOSINE MONOPHOSPHATE-ORTHO-PHENANTHROLINE COMPLEX - 1ST UNAMBIGUOUS EXAMPLE OF O-6 COORDINATION IN A METAL-6-OXOPURINE COMPLEX [J].
GELLERT, RW ;
FISCHER, BE ;
BAU, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (26) :7812-7815
[18]   Metals in anticancer therapy: Copper(II) complexes as inhibitors of the 20S proteasome [J].
Hindo, Sarmad Sahiel ;
Frezza, Michael ;
Tomco, Dajena ;
Heeg, Mary Jane ;
Hryhorczuk, Lew ;
McGarvey, Bruce R. ;
Dou, Q. Ping ;
Verani, Claudio N. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2009, 44 (11) :4353-4361
[19]   Synthesis and single-crystal structures of two copper(II) complexes and one iron(II) complex prepared by in situ ligand substitution at room temperature [J].
Huang, W ;
Qian, HF .
TRANSITION METAL CHEMISTRY, 2006, 31 (05) :621-629
[20]  
John C.L., 1996, PROGR CELL CYCLE RES, V2