5-(Phenylthiomethyl)-2′-deoxyuridine as an efficient photoreactive precursor to generate single and multiple lesions within DNA fragments

被引：17

作者：

Bellon, S ^{[1
]}

Gasparutto, D ^{[1
]}

Romieu, A ^{[1
]}

Cadet, J ^{[1
]}

机构：

[1] CEA Grenoble, Lab Les Acides Nucl, Serv Chim Inorgan & Biol, UMR 5046,Dept Rech Fondamentale Mat Condensee, F-38054 Grenoble 9, France

来源：

NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS | 2001年 / 20卷 / 4-7期

关键词：

D O I：

10.1081/NCN-100002470

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

5-(Phenylthiomethyl)-2'-deoxyuridine was successfully incorporated into DNA oligomers by automated DNA synthesis using phosphoramidite chemistry. UV exposure of the latter thionucleoside containing oligonucleotides under anaerobic and aerobic conditions gives rise to specific base lesions. The photoproducts have been isolated and further characterized on the basis of NMR and mass spectrometric analyses.

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页码：967 / 971

页数：5

相关论文

共 14 条

[1] Chemistry of β-(acyloxy)alkyl and β-(phosphatoxy)alkyl radicals and related species:: Radical and radical ionic migrations and fragmentations of carbon-oxygen bonds [J].

Beckwith, ALJ ;

Crich, D ;

Duggan, PJ ;

Yao, QW .

CHEMICAL REVIEWS, 1997, 97 (08) :3273-3312

[2] Tandem lesions and other products in X-irradiated DNA oligomers [J].

Box, HC ;

Budzinski, EE ;

Dawidzik, JB ;

Wallace, JC ;

Iijima, H .

RADIATION RESEARCH, 1998, 149 (05) :433-439

[3] Free radical-induced tandem base damage in DNA oligomers [J].

Box, HC ;

Budzinski, EE ;

Dawidzik, JB ;

Gobey, JS ;

Freund, HG .

FREE RADICAL BIOLOGY AND MEDICINE, 1997, 23 (07) :1021-1030

[4] Radiation-induced formation of a crosslink between base moieties of deoxyguanosine and thymidine in deoxygenated solutions of d(CpGpTpA) [J].

Box, HC ;

Budzinski, EE ;

Dawidzik, JD ;

Wallace, JC ;

Evans, MS ;

Gobey, JS .

RADIATION RESEARCH, 1996, 145 (05) :641-643

[5]

Budzinski EE, 1997, INT J RADIAT BIOL, V71, P327, DOI 10.1080/095530097144210

[6] Hydroxyl radicals and DNA base damage [J].

Cadet, J ;

Delatour, T ;

Douki, T ;

Gasparutto, D ;

Pouget, JP ;

Ravanat, JL ;

Sauvaigo, S .

MUTATION RESEARCH-FUNDAMENTAL AND MOLECULAR MECHANISMS OF MUTAGENESIS, 1999, 424 (1-2) :9-21

[7] SENSITIZED PHOTOOXIDATION OF THYMIDINE BY 2-METHYL-1-1,4-NAPHTHOQUINONE - CHARACTERIZATION OF THE STABLE PHOTOPRODUCTS [J].

DECARROZ, C ;

WAGNER, JR ;

VANLIER, JE ;

KRISHNA, CM ;

RIESZ, P ;

CADET, J .

INTERNATIONAL JOURNAL OF RADIATION BIOLOGY, 1986, 50 (03) :491-505

[8] A novel vicinal lesion obtained from the oxidative photosensitization of TpdG: Characterization and mechanistic aspects [J].

Delatour, T ;

Douki, T ;

Gasparutto, D ;

Brochier, MC ;

Cadet, J .

CHEMICAL RESEARCH IN TOXICOLOGY, 1998, 11 (09) :1005-1013

[9] 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

[10] Characterization and chemical stability of photooxidized oligonucleotides that contain 2,2-diamino-4-[(2-deoxy-β-D-erythro-pentofuranosyl)amino]-5(2H)-oxazolone [J].

Gasparutto, D ;

Ravanat, JL ;

Gérot, O ;

Cadet, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (40) :10283-10286