The triplet energy of thymine in DNA

被引:91
作者
Bosca, Francisco
Lhiaubet-Vallet, Virginie
Cuquerella, M. Consuelo
Castell, Jose V.
Miranda, Miguel A.
机构
[1] Univ Politecn Valencia, CSIC, Inst Tecnol Quim, Valencia 46022, Spain
[2] Hosp Univ La Fe, Ctr Invest, Valencia 46009, Spain
关键词
D O I
10.1021/ja060651g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Norfloxacin (NFX) photosensitizes formation of thymine dimers (T<>T) in DNA, while its N(4′) acetyl derivative (ANFX) does not. This is evident from the observation of single-strand breaks after enzymatic treatment with T4 endonuclease V and subsequent gel electrophoresis. The triplet energies of NFX and ANFX are estimated at 273 and 268 kJ/mol, respectively, on the basis of triplet-triplet energy transfer quenching by a set of biphenyl and naphthalene derivatives. Hence, the triplet energy of thymine in DNA (i.e., the value for a photosensitizer to produce T<>T) can be estimated at 270 kJ/mol. Copyright © 2006 American Chemical Society.
引用
收藏
页码:6318 / 6319
页数:2
相关论文
共 21 条
[1]   Photophysics and photochemistry of fluoroquinolones [J].
Albini, A ;
Monti, S .
CHEMICAL SOCIETY REVIEWS, 2003, 32 (04) :238-250
[2]  
BENSASON RV, 1983, FLASH PHOTOLYSIS PUL
[3]   DISTRIBUTION OF ULTRAVIOLET-INDUCED LESIONS IN SIMIAN VIRUS-40 DNA [J].
BOURRE, F ;
RENAULT, G ;
SEAWELL, PC ;
SARASIN, A .
BIOCHIMIE, 1985, 67 (3-4) :293-299
[4]   Ultraviolet radiation-mediated damage to cellular DNA [J].
Cadet, J ;
Sage, E ;
Douki, T .
MUTATION RESEARCH-FUNDAMENTAL AND MOLECULAR MECHANISMS OF MUTAGENESIS, 2005, 571 (1-2) :3-17
[5]   Role of excited state intramolecular charge transfer in the photophysical properties of norfloxacin and its derivatives [J].
Cuquerella, MC ;
Miranda, MA ;
Bosca, F .
JOURNAL OF PHYSICAL CHEMISTRY A, 2006, 110 (08) :2607-2612
[6]   Photonucleophilic aromatic substitution of 6-fluoroquinolones in basic media:: Triplet quenching by hydroxide anion [J].
Cuquerella, MC ;
Boscá, F ;
Miranda, MA .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (21) :7256-7261
[7]   Photosensitization of thymine nucleobase by benzophenone through energy transfer, hydrogen abstraction and one-electron oxidation [J].
Delatour, T ;
Douki, T ;
D'Ham, C ;
Cadet, J .
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY B-BIOLOGY, 1998, 44 (03) :191-198
[8]   Individual determination of the yield of the main UV-induced dimeric pyrimidine photoproducts in DNA suggests a high mutagenicity of CC photolesions [J].
Douki, T ;
Cadet, J .
BIOCHEMISTRY, 2001, 40 (08) :2495-2501
[9]   Photosensitization of thymine nucleobase by benzophenone derivatives as models for photoinduced DNA damage: Paterno-Buchi vs energy and electron transfer processes [J].
Encinas, S ;
Belmadoui, N ;
Climent, MJ ;
Gil, S ;
Miranda, MA .
CHEMICAL RESEARCH IN TOXICOLOGY, 2004, 17 (07) :857-862
[10]   Interaction of triplet photosensitizers with nucleotides and DNA in aqueous solution at room temperature [J].
Gut, IG ;
Wood, PD ;
Redmond, RW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (10) :2366-2373