Cytosine-gated hole creation and transfer in DNA in aqueous solution

被引:32
作者
Anderson, Robert F. [1 ]
Shinde, Sujata S. [1 ]
Maroz, Andrej [1 ]
机构
[1] Univ Auckland, Dept Chem, Auckland 1, New Zealand
关键词
DISTANCE CHARGE-TRANSPORT; FLASH-QUENCH TECHNIQUE; ELECTRON-TRANSFER; IONIZATION-POTENTIALS; HOPPING MECHANISM; PULSE-RADIOLYSIS; OXIDATIVE DAMAGE; STRAND BREAKAGE; PROTON-TRANSFER; BASE RADICALS;
D O I
10.1021/ja0658416
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The selenite radical, SeO3-, has been found to selectively produce the cytosyl radical upon one-electron oxidation of duplex DNA. This is at first a surprising result as SeO3- can only oxidize guanine of the DNA bases, implying that the transiently formed guanyl radical cation must transpose into the neutral cytosyl radical with loss of a proton. Back oxidation to produce the neutral guanyl radical, in competition with another fixation reaction, is observed. Copyright © 2006 American Chemical Society.
引用
收藏
页码:15966 / 15967
页数:2
相关论文
共 33 条
[1]   ELECTRON-TRANSFER IN DI(DEOXY)NUCLEOSIDE PHOSPHATES IN AQUEOUS-SOLUTION - RAPID MIGRATION OF OXIDATIVE DAMAGE (VIA ADENINE) TO GUANINE [J].
CANDEIAS, LP ;
STEENKEN, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (06) :2437-2440
[2]   STRUCTURE AND ACID-BASE PROPERTIES OF ONE-ELECTRON-OXIDIZED DEOXYGUANOSINE, GUANOSINE, AND 1-METHYLGUANOSINE [J].
CANDEIAS, LP ;
STEENKEN, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (03) :1094-1099
[3]   Calculation of the ionization potentials of the DNA bases in aqueous medium [J].
Close, DM .
JOURNAL OF PHYSICAL CHEMISTRY A, 2004, 108 (46) :10376-10379
[4]   ABINITIO MOLECULAR-ORBITAL CALCULATIONS ON DNA-BASE PAIR RADICAL IONS - EFFECT OF BASE-PAIRING ON PROTON-TRANSFER ENERGIES, ELECTRON-AFFINITIES, AND IONIZATION-POTENTIALS [J].
COLSON, AO ;
BESLER, B ;
SEVILLA, MD .
JOURNAL OF PHYSICAL CHEMISTRY, 1992, 96 (24) :9787-9794
[5]   GAMMA-RADIOLYSIS OF POLY(U) IN AQUEOUS-SOLUTION - THE ROLE OF PRIMARY SUGAR AND BASE RADICALS IN THE RELEASE OF UNDAMAGED URACIL [J].
DEEBLE, DJ ;
VONSONNTAG, C .
INTERNATIONAL JOURNAL OF RADIATION BIOLOGY, 1984, 46 (03) :247-260
[7]   Oxidative DNA damage through long-range electron transfer [J].
Hall, DB ;
Holmlin, RE ;
Barton, JK .
NATURE, 1996, 382 (6593) :731-735
[8]   Spiers Memorial Lecture: On the hypothesis of cathodic protection of genes [J].
Heller, A .
FARADAY DISCUSSIONS, 2000, 116 :1-13
[9]   Long-distance charge transport in duplex DNA: The phonon-assisted polaron-like hopping mechanism [J].
Henderson, PT ;
Jones, D ;
Hampikian, G ;
Kan, YZ ;
Schuster, GB .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1999, 96 (15) :8353-8358
[10]   ESR-SPECTRA OF RADICALS OF SINGLE-STRANDED AND DOUBLE-STRANDED DNA IN AQUEOUS-SOLUTION - IMPLICATIONS FOR OH-INDUCED STRAND BREAKAGE [J].
HILDENBRAND, K ;
SCHULTEFROHLINDE, D .
FREE RADICAL RESEARCH COMMUNICATIONS, 1990, 11 (4-5) :195-206