DNA-fiber EPR study of the orientation of Cu(II) complexes of 1,10-phenanthroline and its derivatives bound to DNA: mono(phenanthroline)-copper(II) and its ternary complexes with amino acids

被引:161
作者
Chikira, M
Tomizawa, Y
Fukita, D
Sugizaki, T
Sugawara, N
Yamazaki, T
Sasano, A
Shindo, H
Palaniandavar, M
Antholine, WE
机构
[1] Chuo Univ, Dept Appl Chem, Bunkyo Ku, Tokyo 1128551, Japan
[2] Tokyo Univ Pharm & Life Sci, Sch Pharm, Tokyo 1920392, Japan
[3] Bharathidasan Univ, Dept Chem, Tiruchirappalli 620024, Tamil Nadu, India
[4] Med Coll Wisconsin, Biophys Res Inst, Milwaukee, WI 53226 USA
关键词
copper; DNA fiber; electron paramagnetic resonance (EPR); phenanthroline; ternary complex;
D O I
10.1016/S0162-0134(02)00378-1
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
The orientation of mono(1,10-phenanthroline)copper(II), [Cu(phen)](2+), and the ternary complexes with amino acids, [Cu(phen)X-aa](n+), where X-aa stands for an alpha-amino acid, has been investigated by electron paramagnetic resonance (EPR) spectra of the complexes on DNA fibers. It has been revealed that these complexes bind to DNA with several different binding modes. The observation of a species whose g(parallel to) axis is almost parallel to the DNA double helical axis has suggested that the phenanthroline moiety intercalates to DNA. An absence of the intercalated species for the corresponding 2,2'-bipyridine complex has shown that the three-fused aromatic rings in phenanthroline are critical for the intercalative binding of the complexes. The intercalative binding was promoted by 5,6-dimethyl groups on the phenanthroline ring, whereas it was disturbed by 2,9-dimethyl groups, indicating that the planarity of the coordination sphere is important for the intercalative binding. In all cases, the amount of the non-intercalated species was larger than that of the intercalated one. The amino acids in the ternary complexes of glycine, leucine, serine, threonine, cysteine, methionine, and asparagine were partly substituted with some coordinating groups in DNA, whereas the ternary complexes of lysine, arginine, and glutamine remained intact on DNA. (C) 2002 Elsevier Science Inc. All rights reserved.
引用
收藏
页码:163 / 173
页数:11
相关论文
共 42 条
[31]   DNA-stacking interactions determine the sequence specificity of the deoxyribonuclease activity of 1,10-phenanthroline-copper ion [J].
Schaeffer, F ;
Rimsky, S ;
Spassky, A .
JOURNAL OF MOLECULAR BIOLOGY, 1996, 260 (04) :523-539
[32]   NONUNIFORM BACKBONE CONFORMATION OF DEOXYRIBONUCLEIC-ACID INDICATED BY P-31 NUCLEAR MAGNETIC-RESONANCE CHEMICAL-SHIFT ANISOTROPY [J].
SHINDO, H ;
WOOTEN, JB ;
PHEIFFER, BH ;
ZIMMERMAN, SB .
BIOCHEMISTRY, 1980, 19 (03) :518-526
[33]   P-31 NUCLEAR MAGNETIC-RESONANCE OF HIGHLY ORIENTED DNA FIBERS .1. STATIC GEOMETRY OF DNA DOUBLE HELICES [J].
SHINDO, H ;
FUJIWARA, T ;
AKUTSU, H ;
MATSUMOTO, U ;
KYOGOKU, Y .
BIOCHEMISTRY, 1985, 24 (04) :887-895
[34]  
Sigman DS, 1996, MET IONS BIOL SYST, V33, P485
[35]  
SIGMAN DS, 1979, J BIOL CHEM, V254, P2269
[36]   CHEMICAL NUCLEASES [J].
SIGMAN, DS ;
MAZUMDER, A ;
PERRIN, DM .
CHEMICAL REVIEWS, 1993, 93 (06) :2295-2316
[37]   NONCOVALENT DNA-BINDING OF BIS(1,10-PHENANTHROLINE)COPPER(I) AND RELATED-COMPOUNDS [J].
VEAL, JM ;
RILL, RL .
BIOCHEMISTRY, 1991, 30 (04) :1132-1140
[38]  
VEAL JM, 1991, NUCLEIC ACIDS RES, V19, P3383
[39]   SEQUENCE SPECIFICITY OF DNA CLEAVAGE BY BIS(1,10-PHENANTHROLINE)COPPER(I) - EFFECTS OF SINGLE BASE PAIR TRANSITIONS ON THE CLEAVAGE OF PREFERRED PYRIMIDINE-PURINE-PYRIMIDINE TRIPLETS [J].
VEAL, JM ;
RILL, RL .
BIOCHEMISTRY, 1989, 28 (08) :3243-3250
[40]   ESR LINEWIDTHS IN SOLUTION .4. EXPERIMENTAL STUDIES OF ANISOTROPIC AND SPIN-ROTATIONAL EFFECTS IN COPPER COMPLEXES [J].
WILSON, R ;
KIVELSON, D .
JOURNAL OF CHEMICAL PHYSICS, 1966, 44 (12) :4445-&