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
[1]   Human neutrophils employ the myeloperoxidase-hydrogen peroxide-chloride system to convert hydroxy-amino acids into glycolaldehyde, 2-hydroxypropanal, and acrolein - A mechanism for the generation of highly reactive alpha-hydroxy and alpha,beta-unsaturated aldehydes by phagocytes at sites of inflammation [J].
Anderson, MM ;
Hazen, SL ;
Hsu, FF ;
Heinecke, JW .
JOURNAL OF CLINICAL INVESTIGATION, 1997, 99 (03) :424-432
[2]  
BALAGURUMOORTHY P, 1994, J BIOL CHEM, V269, P21858
[3]   Protein-bound acrolein: A novel marker of oxidative stress in Alzheimer's disease [J].
Calingasan, NY ;
Uchida, K ;
Gibson, GE .
JOURNAL OF NEUROCHEMISTRY, 1999, 72 (02) :751-756
[4]   Cdc13 both positively and negatively regulates telomere replication [J].
Chandra, A ;
Hughes, TR ;
Nugent, CI ;
Lundblad, V .
GENES & DEVELOPMENT, 2001, 15 (04) :404-414
[5]   Unusual DNA duplex and hairpin motifs [J].
Chou, SH ;
Chin, KH ;
Wang, AHJ .
NUCLEIC ACIDS RESEARCH, 2003, 31 (10) :2461-2474
[6]   Recombination-mediated lengthening of terminal telomeric repeats requires the Sgs1 DNA helicase [J].
Cohen, H ;
Sinclair, DA .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2001, 98 (06) :3174-3179
[7]  
COHEN SM, 1992, CANCER RES, V52, P3577
[8]  
CROOK TR, 1986, CANCER RES, V46, P5029
[9]   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
[10]   Improved strategies for postoligomerization synthesis of oligodeoxynucleotides bearing structurally defined adducts at the N-2 position of deoxyguanosine [J].
DeCorte, BL ;
Tsarouhtsis, D ;
Kuchimanchi, S ;
Cooper, MD ;
Horton, P ;
Harris, CM ;
Harris, TM .
CHEMICAL RESEARCH IN TOXICOLOGY, 1996, 9 (03) :630-637