Interaction of 9,10-anthraquinone with adenine and 2′-deoxyadenosine

被引:10
作者
Bose, Adity [1 ]
Sarkar, Achintya K. [2 ]
Basu, Samita [1 ]
机构
[1] Saha Inst Nucl Phys, Div Chem Sci, Kolkata 700064, India
[2] Presidency Coll, Dept Chem, Kolkata 700073, India
关键词
9,10-anthraquinone; adenine; 2 '-deoxyadenosine; magnetic field effect; hydrogen bonding; aromaticity;
D O I
10.1016/j.bpc.2008.04.011
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
Laser flash photolysis has been used for the study of the interaction of 9,10-anthraquinone (AQ) with the DNA base, adenine (A) and its corresponding nucleoside, 2'-deoxyadenosine (dA). This study has provided two very important observations. AQ has been found to support electron transfer in different categories of media, acetonitrile/water on one hand and SDS micelles on other. While in our earlier work 2-methyl 1,4-naphthoquinone was found to undergo a switchover in reactivity a. Am. Chem. Soc. 126 (2004) 1058910593). Again A and dA are found to behave differently on account of an extra sugar unit, which not only affects the rate of reaction but the reaction pathway has been found to be modified too. (C) 2008 Elsevier B.V. All rights reserved.
引用
收藏
页码:59 / 65
页数:7
相关论文
共 38 条
[21]   Triplet state mechanism for electron transfer oxidation of DNA [J].
Ma, JH ;
Lin, WZ ;
Wang, WF ;
Han, ZH ;
Yao, SD ;
Lin, NY .
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY B-BIOLOGY, 2000, 57 (01) :76-81
[22]   Characterization of reactive intermediates in laser photolysis of nucleoside using of sodium salt anthraquinone-2-sulfonic acid as photosensitizer [J].
Ma, JH ;
Lin, WZ ;
Wang, WF ;
Han, ZH ;
Yao, SD ;
Lin, NY .
RADIATION PHYSICS AND CHEMISTRY, 1999, 54 (05) :491-497
[23]   Dibenzoyldiazomethane-acridine conjugate: A novel DNA photofootprinting agent [J].
Nakatani, K ;
Shirai, J ;
Sando, S ;
Saito, I .
TETRAHEDRON LETTERS, 1997, 38 (34) :6047-6050
[24]   Direct measurement of excited singlet-state lifetime in the homologous sequence adenine, adenosine, adenosine 5'-monophosphate and in calf thymus DNA [J].
Nikogosyan, DN ;
Angelov, D ;
Soep, B ;
Lindqvist, L .
CHEMICAL PHYSICS LETTERS, 1996, 252 (5-6) :322-326
[25]   MOLECULAR RECOGNITION IN MICELLES - THE ROLES OF HYDROGEN-BONDING AND HYDROPHOBICITY IN ADENINE THYMINE BASE-PAIRING IN SDS MICELLES [J].
NOWICK, JS ;
CHEN, JS ;
NORONHA, G .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (17) :7636-7644
[26]   Influence of d orbital occupation on the binding of metal ions to adenine [J].
Rodgers, MT ;
Armentrout, PB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (11) :2678-2691
[27]   LASER-PHOTOLYSIS STUDY OF THE PHOTOCHEMICAL-REACTIONS OF NAPHTHOQUINONES IN A SODIUM DODECYL-SULFATE MICELLE UNDER HIGH MAGNETIC-FIELDS [J].
SAKAGUCHI, Y ;
HAYASHI, H .
JOURNAL OF PHYSICAL CHEMISTRY, 1984, 88 (07) :1437-1440
[28]   Medium-dependent electron and H atom transfer between 2′-deoxyadenosine and menadione:: A magnetic field effect study [J].
Sengupta, T ;
Choudhury, SD ;
Basu, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (34) :10589-10593
[29]   Characterization of reactive intermediates in laser photolysis of guanine and its derivatives using acetone as photosensitizer: The pH dependence [J].
Song, QH ;
Yao, SD ;
Li, HC ;
Zuo, ZH ;
Zhang, JS ;
Lin, NY .
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 1996, 95 (03) :223-229