Interchain cross-linking of DNA mediated by the principal adduct of acrolein

被引：61

作者：

Kozekov, ID

Nechev, LV

Sanchez, A

Harris, CM

Lloyd, RS

Harris, TM

机构：

[1] Vanderbilt Univ, Dept Chem, Nashville, TN 37235 USA

[2] Vanderbilt Univ, Ctr Mol Toxicol, Nashville, TN 37235 USA

[3] Univ Texas, Med Branch, Sealy Ctr Mol Sci, Galveston, TX 77555 USA

来源：

CHEMICAL RESEARCH IN TOXICOLOGY | 2001年 / 14卷 / 11期

关键词：

D O I：

10.1021/tx010127h

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A DNA duplex containing the primary acrolein adduct, 3-(2-deoxy-beta -D-erythro-pentofuranosyl)-5,6,7,8-tetrahydro-8-hydroxypyrimido[1,2-a]purin-10(3H)-one (2), of deoxyguanosine in a 5'-CpG sequence context spontaneously but reversibly formed an interchain cross-link with the exocyclic amino group of deoxyguanosine in the opposing chain. The linkage was sufficiently stable that the cross-linked duplex could be isolated by HPLC and characterized by MALDI-TOF mass spectrometry. Enzymatic degradation gave his-nucleoside 6, which was independently prepared by direct reaction of 2 with dGuo.

引用

收藏

页码：1482 / 1485

页数：4

相关论文

共 17 条

[1] A CRITICAL-REVIEW OF THE LITERATURE ON ACROLEIN TOXICITY [J].

BEAUCHAMP, RO ;

ANDJELKOVICH, DA ;

KLIGERMAN, AD ;

MORGAN, KT ;

HECK, HD .

CRC CRITICAL REVIEWS IN TOXICOLOGY, 1985, 14 (04) :309-380

[2] Endogenous formation and significance of 1,N2-propanodeoxyguanosine adducts [J].

Chung, FL ;

Nath, RG ;

Nagao, M ;

Nishikawa, A ;

Zhou, GD ;

Randerath, K .

MUTATION RESEARCH-FUNDAMENTAL AND MOLECULAR MECHANISMS OF MUTAGENESIS, 1999, 424 (1-2) :71-81

[3]

CHUNG FL, 1984, CANCER RES, V44, P990

[4]

Chung FL, 2000, CANCER RES, V60, P1507

[5] NMR characterization of a DNA duplex containing the major acrolein-derived deoxyguanosine adduct γ-OH-1,N2-propano-2′-deoxyguanosine [J].

de los Santos, C ;

Zaliznyak, T ;

Johnson, F .

JOURNAL OF BIOLOGICAL CHEMISTRY, 2001, 276 (12) :9077-9082

[6] Structural studies of an oligodeoxynucleotide containing a trimethylene interstrand cross-link in a 5′-(CpG) motif:: Model of a malondialdehyde cross-link [J].

Dooley, PA ;

Tsarouhtsis, D ;

Korbel, GA ;

Nechev, LV ;

Shearer, J ;

Zegar, IS ;

Harris, CM ;

Stone, MP ;

Harris, TM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (08) :1730-1739

[7] FORMATION OF 1,N2-ETHENOGUANINE AND N2,3-ETHENOGUANINE FROM 2-HALOOXIRANES - ISOTOPIC LABELING STUDIES AND ISOLATION OF A HEMIAMINAL DERIVATIVE OF N2-(2-OXOETHYL)GUANINE [J].

GUENGERICH, FP ;

PERSMARK, M ;

HUMPHREYS, WG .

CHEMICAL RESEARCH IN TOXICOLOGY, 1993, 6 (05) :635-648

[8] 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

[9] 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

[10] DETECTION OF EXOCYCLIC 1,N-2-PROPANODEOXYGUANOSINE ADDUCTS AS COMMON DNA LESIONS IN RODENTS AND HUMANS [J].

NATH, RG ;

CHUNG, FL .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1994, 91 (16) :7491-7495