Detection of an interchain carbinolamine cross-link formed in a CpG sequence by the acrolein DNA adduct γ-Oh-1,N2-propano-2′-deoxyguanosine

被引:48
作者
Kim, HYH
Voehler, M
Harris, TM
Stone, MP
机构
[1] Vanderbilt Univ, Dept Chem, Ctr Mol Toxicol, Nashville, TN 37235 USA
[2] Vanderbilt Univ, Vanderbilt Ingram Canc Ctr, Nashville, TN 37235 USA
关键词
D O I
10.1021/ja020333r
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Spectroscopic evidence is presented for the formation of a carbinolamine interchain cross-link in 5′-CpG-3′ sequences, arising from the acrolein adduct γ-OH-PdG. This may be important in understanding biological processing of acrolein-induced DNA damage in CpG sequences. Copyright © 2002 American Chemical Society.
引用
收藏
页码:9324 / 9325
页数:2
相关论文
共 34 条
[11]   THE 3-DIMENSIONAL STRUCTURE IN SOLUTION (PH 5.8) OF A DNA 9-MER DUPLEX CONTAINING 1,N2-PROPANODEOXYGUANOSINE OPPOSITE DEOXYADENOSINE - RESTRAINED MOLECULAR-DYNAMICS AND NOE-BASED REFINEMENT CALCULATIONS [J].
HUANG, P ;
EISENBERG, M .
BIOCHEMISTRY, 1992, 31 (28) :6518-6532
[12]   Molecular analysis of mutations induced by acrolein in human fibroblast cells using supF shuttle vector plasmids [J].
Kawanishi, M ;
Matsuda, T ;
Nakayama, A ;
Takebe, H ;
Matsui, S ;
Yagi, T .
MUTATION RESEARCH-GENETIC TOXICOLOGY AND ENVIRONMENTAL MUTAGENESIS, 1998, 417 (2-3) :65-73
[13]   Postsynthetic generation of a major acrolein adduct of 2′-deoxyguanosine in oligomeric DNA [J].
Khullar, S ;
Varaprasad, CV ;
Johnson, F .
JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (06) :947-950
[14]   NMR-STUDIES OF EXOCYCLIC 1,N2-PROPANODEOXYGUANOSINE ADDUCTS (X) OPPOSITE PURINES IN DNA DUPLEXES - PROTONATED X(SYN).A(ANTI) PAIRING (ACIDIC PH) AND X(SYN).G(ANTI) PAIRING (NEUTRAL PH) AT THE LESION SITE [J].
KOUCHAKDJIAN, M ;
MARINELLI, E ;
GAO, XL ;
JOHNSON, F ;
GROLLMAN, A ;
PATEL, D .
BIOCHEMISTRY, 1989, 28 (13) :5647-5657
[15]   Interchain cross-linking of DNA mediated by the principal adduct of acrolein [J].
Kozekov, ID ;
Nechev, LV ;
Sanchez, A ;
Harris, CM ;
Lloyd, RS ;
Harris, TM .
CHEMICAL RESEARCH IN TOXICOLOGY, 2001, 14 (11) :1482-1485
[16]   Repair of an interstrand DNA cross-link initiated by ERCC1-XPF repair/recombination nuclease [J].
Kuraoka, I ;
Kobertz, WR ;
Ariza, RR ;
Biggerstaff, M ;
Essigmann, JM ;
Wood, RD .
JOURNAL OF BIOLOGICAL CHEMISTRY, 2000, 275 (34) :26632-26636
[17]   Duplex DNA catalyzes the chemical rearrangement of a malondialdehyde deoxyguanosine adduct [J].
Mao, H ;
Schnetz-Boutaud, NC ;
Weisenseel, JP ;
Marnett, LJ ;
Stone, MP .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1999, 96 (12) :6615-6620
[18]   Solution structure of an oligodeoxynucleotide containing the malondialdehyde deoxyguanosine adduct N2-(3-oxo-1-propenyl)-dG (ring-opened M1G) positioned in a (CpG)3 frameshift hotspot of the Salmonella typhimurium hisD3052 gene [J].
Mao, H ;
Reddy, GR ;
Marnett, LJ ;
Stone, MP .
BIOCHEMISTRY, 1999, 38 (41) :13491-13501
[19]  
MARNETT LJ, 1985, MUTAT RES, V148, P25
[20]   IMPROVED SENSITIVITY OF HSQC SPECTRA OF EXCHANGING PROTONS AT SHORT INTERSCAN DELAYS USING A NEW FAST HSQC (FHSQC) DETECTION SCHEME THAT AVOIDS WATER SATURATION [J].
MORI, S ;
ABEYGUNAWARDANA, C ;
JOHNSON, MO ;
VANZIJL, PCM .
JOURNAL OF MAGNETIC RESONANCE SERIES B, 1995, 108 (01) :94-98