Binary and ternary new water soluble copper(II) complexes of L-tyrosine and substituted 1,10-phenanthrolines: Effect of substitution on DNA interactions and cytotoxicities

被引:30
作者
Inci, Duygu [1 ]
Aydin, Rahmiye [1 ]
Vatan, Ozgur [2 ]
Yilmaz, Dilek [2 ]
Genckal, Hasene Mutlu [1 ]
Zorlu, Yunus [3 ]
Cavas, Tolga [2 ]
机构
[1] Uludag Univ, Fac Arts & Sci, Dept Chem, TR-16059 Bursa, Turkey
[2] Uludag Univ, Fac Arts & Sci, Dept Biol, TR-16059 Bursa, Turkey
[3] Gebze Inst Technol, Fac Sci, Dept Chem, TR-41400 Gebze, Turkey
关键词
Copper(II); 1,10-Phenanthroline; 5-Nitro-1,10-phenanthroline; L-Tyrosine; DNA binding and cleavage; Cytotoxicity; OXIDATIVE CLEAVAGE ACTIVITY; WEAK-INTERACTIONS; CRYSTAL-STRUCTURE; AMINO-ACIDS; BINDING; FLUORESCENCE; DERIVATIVES; MONONUCLEAR; ORGANOTIN(IV); RUTHENIUM(II);
D O I
10.1016/j.saa.2015.03.011
中图分类号
O433 [光谱学];
学科分类号
0703 ; 070302 ;
摘要
Binary and ternary water soluble copper(II) complexes - [Cu(nphen)(2)(H2O)](NO3)(2)center dot H2O (1), [Cu(phen)(2)(H2O)](NO3)(2) (2), [Cu(nphen)(L-tyr)(H2O)]NO3 center dot 2H(2)O (3), [Cu(Phen)(tyr)(H2O)] NO3 center dot 2H(2)O (4) - and diquarternary salts of nphen and phen (nphen = 5-nitro-1,10-phenanthroline, phen = 1,10-phenanthroline and tyr = L-tyrosine) have been synthesized and characterized by CHN analysis, H-1 NMR, C-13 NMR and IR spectroscopy, thermal analysis and single crystal X-ray diffraction techniques. The CT-DNA binding properties of these compounds have been investigated by thermal denaturation measurements, absorption and emission spectroscopy. The supercoiled pUC19 plasmid DNA cleavage activity of these compounds has been explored by agarose gel electrophoresis. The cytotoxicity of these compounds against MCF-7, Caco-2, A549 cancer cells and BEAS-2B healthy cells was also studied by using XTT method. The complexes 1-4 exhibit significant high cytotoxicity with low IC50 values in compared with cisplatin. The effect of the substituents of phen and coordinated amino acid in the above complexes are presented and discussed. (C) 2015 Elsevier B.V. All rights reserved.
引用
收藏
页码:313 / 324
页数:12
相关论文
共 84 条
[1]   SYNTHESIS, STRUCTURE, AND SPECTROSCOPIC PROPERTIES OF COPPER(II) COMPOUNDS CONTAINING NITROGEN SULFUR DONOR LIGANDS - THE CRYSTAL AND MOLECULAR-STRUCTURE OF AQUA[1,7-BIS(N-METHYLBENZIMIDAZOL-2'-YL)-2,6-DITHIAHEPTANE]COPPER(II) PERCHLORATE [J].
ADDISON, AW ;
RAO, TN ;
REEDIJK, J ;
VANRIJN, J ;
VERSCHOOR, GC .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1984, (07) :1349-1356
[2]  
ALESSIO E, 2011, BIOINORGANIC MED CHE
[3]   Copper(II) complexes of tridentate pyridylmethylethylenediamines: Role of ligand steric hindrance on DNA binding and cleavage [J].
Angamuthu, R ;
Rajendiran, V ;
Maheswari, PU ;
Balamurugan, R ;
Kilner, CA ;
Halcrow, MA ;
Palaniandavar, M .
JOURNAL OF INORGANIC BIOCHEMISTRY, 2005, 99 (08) :1717-1732
[4]  
[Anonymous], 2008, BRUK SADABS V2008 1
[5]  
[Anonymous], 2012, BRUK APEX2 V2012 4 0
[6]   Mechanistic insight into the cellular uptake and processing of cisplatin 30 years after its approval by FDA [J].
Arnesano, Fabio ;
Natile, Giovanni .
COORDINATION CHEMISTRY REVIEWS, 2009, 253 (15-16) :2070-2081
[7]  
Arumugham MN., 2013, International Journal of Inorganic and Bioinorganic Chemistry, V3, P8
[8]   TRIS(PHENANTHROLINE)RUTHENIUM(II) - STEREOSELECTIVITY IN BINDING TO DNA [J].
BARTON, JK ;
DANISHEFSKY, AT ;
GOLDBERG, JM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (07) :2172-2176
[9]  
BERG JM, 1989, MET IONS BIOL SYST, V25, P235
[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