Effect of γ-hydroxypropano deoxyguanosine, the major acrolein-derived adduct, on monomolecular quadruplex structure of telomeric repeat d(TTAGGG)4

被引:4
作者
D'Isa, G
Galeone, A
Oliviero, G
Piccialli, G
Varra, M
Mayol, L
机构
[1] Univ Naples Federico II, Dipartimento Chim Sostanze Nat, Fac Farm, I-80131 Naples, Italy
[2] Univ Naples Federico II, Dipartimento Chim Sostanze Nat, Fac Sci Biotecnol, I-80131 Naples, Italy
关键词
acrolein; telomeric repeat; quadruplex;
D O I
10.1016/j.bmcl.2004.07.074
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
The three oligodeoxyribonucleotides (ODNs) a-c, having the telomeric repeat d(TTAGGG)(4) sequence and incorporating gamma-hydroxypropano deoxyguanosine at different positions, were synthesized. Gel electrophoresis and CD analyses indicated that the ODNs assume monomolecular quadruplex structures in Na+ and in K+ buffers. The T-m values, obtained by CD melting experiments, showed that the presence of the acrolein-dG adduct into the ODN b decreases the thermal stability of the monomolecular quadruplex structure in Na+ solution, whereas for a and c no significant effect could be detected in the same experimental conditions. On the contrary, all ODNs a-d show the same behaviour in K+ buffer. These findings are briefly discussed. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5417 / 5421
页数:5
相关论文
共 49 条
[11]  
Evans SK, 2000, J CELL SCI, V113, P3357
[12]   TOXICITY, INTERSTRAND CROSS-LINKS AND DNA FRAGMENTATION INDUCED BY ACTIVATED CYCLOPHOSPHAMIDE IN YEAST - COMPARATIVE STUDIES ON 4-HYDROPEROXY-CYCLOPHOSPHA-MIDE, ITS MONOFUNCTIONAL ANALOGON, ACROLEIN, PHOSPHORAMIDE MUSTARD, AND NOR-NITROGEN MUSTARD [J].
FLEER, R ;
BRENDEL, M .
CHEMICO-BIOLOGICAL INTERACTIONS, 1982, 39 (01) :1-15
[13]   Error prone translesion synthesis past γ-hydroxypropano deoxyguanosine, the primary acrolein-derived adduct in mammalian cells [J].
Kanuri, M ;
Minko, IG ;
Nechev, LV ;
Harris, TM ;
Harris, CM ;
Lloyd, RS .
JOURNAL OF BIOLOGICAL CHEMISTRY, 2002, 277 (21) :18257-18265
[14]   Formation of acrolein-derived 2′-deoxyadenosine adduct in an iron-induced carcinogenesis model [J].
Kawai, Y ;
Furuhata, A ;
Toyokuni, S ;
Aratani, Y ;
Uchida, K .
JOURNAL OF BIOLOGICAL CHEMISTRY, 2003, 278 (50) :50346-50354
[15]   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
[16]   The molecular effects of acrolein [J].
Kehrer, JP ;
Biswal, SS .
TOXICOLOGICAL SCIENCES, 2000, 57 (01) :6-15
[17]   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
[18]   Detection of an interchain carbinolamine cross-link formed in a CpG sequence by the acrolein DNA adduct γ-Oh-1,N2-propano-2′-deoxyguanosine [J].
Kim, HYH ;
Voehler, M ;
Harris, TM ;
Stone, MP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (32) :9324-9325
[19]   TIN2, a new regulator of telomere length in human cells [J].
Kim, SH ;
Kaminker, P ;
Campisi, J .
NATURE GENETICS, 1999, 23 (04) :405-412
[20]   DNA interchain cross-links formed by acrolein and crotonaldehyde [J].
Kozekov, ID ;
Nechev, LV ;
Moseley, MS ;
Harris, CM ;
Rizzo, CJ ;
Stone, MP ;
Harris, TM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (01) :50-61