Sequence-dependent formation of intrastrand crosslink products from the UVB irradiation of duplex DNA containing a 5-bromo-2′-deoxyuridine or 5-bromo-2′-deoxycytidine

Nucleic Acids Research

Volumn 34, Issue 22, 2006, Pages 6521-6529

  Zeng, Yu ^a   Wang, Yinsheng ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALINE PHOSPHATASE; BROMODEOXYCYTIDINE; BROXURIDINE; DINUCLEOSIDE PHOSPHATE; NUCLEASE; NUCLEOSIDE; OLIGONUCLEOTIDE; PHOSPHODIESTERASE; PYRIMIDINE;

ARTICLE; DNA CROSS LINKING; DNA DAMAGE; DNA REPLICATION; ELECTROSPRAY MASS SPECTROMETRY; HERPES SIMPLEX VIRUS 1; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IONIZING RADIATION; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NONHUMAN; NUCLEIC ACID STRUCTURE; NUCLEOTIDE SEQUENCE; PHOTOSENSITIZATION; PRIORITY JOURNAL; PROTEIN CROSS LINKING; ULTRAVIOLET IRRADIATION;

BASE SEQUENCE; BROMODEOXYCYTIDINE; BROMODEOXYURIDINE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CHROMATOGRAPHY, LIQUID; DNA; OLIGODEOXYRIBONUCLEOTIDES; TANDEM MASS SPECTROMETRY; ULTRAVIOLET RAYS;

EID: 33845869020     PISSN: 03051048     EISSN: 13624962     Source Type: Journal    
DOI: 10.1093/nar/gkl892     Document Type: Article

References (35)

1. Dewey,W.C. and Humphrey,R.M. (1965) Increase in radiosensitivity to ionizing radiation related to replacement of thymidine in mammalian cells with 5-bromodeoxyuridine. Radiat. Res., 26, 538-553.
2. Sano,K., Hoshino,T. and Nagai,M. (1968) Radiosensitization of brain tumor cells with a thymidine analogue (bromouridine). J. Neurosurg., 28, 530-538.
3. Ling,L.L. and Ward,J.F. (1990) Radiosensitization of Chinese hamster V79 cells by bromodeoxyuridine substitution of thymidine: Enhancement of radiation-induced toxicity and DNA strand break production by monofilar and bifilar substitution. Radiat. Res., 121, 76-83.
4. Webb,C.F., Jone,G.D., Moyer,D.J., Aguilera,J.A. and Ling,L.L. (1993) Mechanisms of radiosensitization in bromodeoxyuridine-substituted cells. Int. J. Radiat. Biol., 64, 695-705.
5. Taguchi,T. and Shiraishi,Y. (1989) Increased sister-chromatid exchanges (SCEs) and chromosomal fragilities by BrdU in a human mutant B-lymphoblastoid cell line. Mutat. Res., 211, 43-49.
6. Cadet,J. and Vigny,P. (1990) In Morrison,H. (ed.), Bioorganic Photochemistry. John Wiley, New York, Vol. 1, pp. 1.
7. Ribas,M., Korenberg,J.R., Peretti,D., Pichiri,G., Stockert,J.C., Gosalvez,J. and Mezzanotte,R. (1994) Sister chromatid differentiation in 5-bromo-2′-deoxyuridine-substituted chromosomes: A study with DNA-specific ligands and monoclonal antibody to histone H2B. Chromosome Res., 2, 428-438.
8. Wojcik,A., von Sonntag,C. and Obe,G. (2003) Application of the biotin-dUTP chromosome labelling technique to study the role of 5-bromo-2′-deoxyuridine in the formation of UV-induced sister chromatid exchanges in CHO cells. J. Photochem. Photobiol. B: Biol., 69, 139-144.
9. Sugiyama,H., Tsutsumi,Y. and Saito,I. (1990) Highly sequence-selective photoreaction of 5-bromouracil-containing deoxyhexanucleotides. J. Am. Chem. Soc., 112, 6720-6721.
10. Fuciarelli,A.F., Sisk,E.C. and Zimbrick,J.D. (1994) Electron migration in oligonucleotides upon gamma-irradiation in solution. Int. J. Radiat. Biol., 65, 409-418.
11. Limoli,C.L., Wu,C.C., Milligan,J.R. and Ward,J.F. (1997) Photochemical production of uracil quantified in bromodeoxyuridine-substituted SV40 DNA by uracil DNA glycosylase and a lysyl-tyrosyl-lysine tripeptide. Mutagenesis, 12, 443-447.
12. Chen,T., Cook,G.P., Koppisch,A.T. and Greenberg,M.M. (2000) Investigation of the origin of the sequence selectivity for the 5-halo-2′-deoxyuridine sensitization of DNA to damage by UV-irradiation. J. Am. Chem. Soc., 122, 3861-3866.
13. 2 on the formation of direct strand breaks upon UV irradiation of 5-bromodeoxyuridine-containing oligonucleotides. Chem. Biol., 6, 451-459.
14. Brust,D., Feden,J., Farnsworth,J., Amir,C., Broaddus,W.C. and Valerie,K. (2000) Radiosensitization of rat glioma with bromodeoxycytidine and adenovirus expressing herpes simplex virus-thymidine kinase delivered by slow, rate-controlled positive pressure infusion. Cancer Gene Ther., 7, 778-788.
15. BrCG) and duplex DNA containing 5-bromocytosine. J. Am. Chem. Soc., 126, 6552-6553.
16. Gu,C. and Wang,Y. (2004) LC-MS/MS identification and yeast polymerase eta bypass of a novel gamma-irradiation-induced intrastrand cross-link lesion G[8-5]C. Biochemistry, 43, 6745-6750.
17. BrCA) and duplex DNA containing a 5-bromocytosine. J. Am.Chem. Soc., 127, 13969-13977.
18. Gu,C. and Wang,Y. (2005) Thermodynamic and in vitro replication studies of an intrastrand crosslink lesion G[8-5]C. Biochemistry, 44, 8883-8889.
19. Yang,Z., Colis,L.C., Basu,A.K. and Zou,Y. (2005) Recognition and incision of gamma-radiation-induced cross-linked guanine-thymine tandem lesion G[8,5-Me]T by UvrABC nuclease. Chem. Res. Toxicol., 18, 1339-1346.
20. Gu,C., Zhang,Q., Yang,Z., Wang,Y., Zou,Y. and Wang,Y. (2006) Recognition and incision of oxidative intrastrand cross-link lesions by UvrABC nuclease. Biochemistry, 45, 10739-10746.
21. Cecchini,S., Girouard,S., Huels,M.A., Sanche,L. and Hunting,D.J. (2004) Single-strand-specific radiosensitization of DNA by bromodeoxyuridine. Radiat. Res., 162, 604-615.
22. Cecchini,S., Girouard,S., Huels,M.A., Sanche,L. and Hunting,D.J. (2005) Interstrand cross-links: A new type of gamma-ray damage in bromodeoxyuridine-substituted DNA. Biochemistry, 44, 1932-1940.
23. Cecchini,S., Masson,C., La Madeleine,C., Huels,M.A., Sanche,L., Wagner,J.R. and Hunting,D.J. (2005) Interstrand cross-link induction by UV radiation in bromodeoxyuridine-substituted DNA: Dependence on DNA conformation. Biochemistry, 44, 16957-16966.
24. Liu,Z., Gao,Y. and Wang,Y. (2003) Identification and characterization of a novel cross-link lesion in d(CpC) upon 365-nm irradiation in the presence of 2-methyl-1,4-naphthoquinone. Nucleic Acids Res., 31, 5413-5424.
25. Zhang,Q. and Wang,Y. (2003) Independent generation of 5-(2′-deoxycytidinyl)methyl radical and the formation of a novel crosslink lesion between 5-methylcytosine and guanine. J. Am. Chem. Soc., 125, 12795-12802.
26. Liu,Z., Gao,Y., Zeng,Y., Fang,F., Chi,D. and Wang,Y. (2004) Isolation and characterization of a novel cross-link lesion in d(CpC) induced by one-electron photooxidation. Photochem. Photobiol., 80, 209-215.
27. Bellon,S., Ravanat,J.L., Gasparutto,D. and Cadet,J. (2002) Cross-linked thymine-purine base tandem lesions: Synthesis, characterization, and measurement in gamma-irradiated isolated DNA. Chem. Res. Toxicol., 15, 598-606.
28. Zhang,Q. and Wang,Y. (2005) Generation of 5-(2′-deoxycytidyl)methyl radical and the formation of intrastrand cross-link lesions in oligodeoxyribonucleotides. Nucleic Acids Res., 33, 1593-1603.
29. West,R.T., Garza,L.A., 2nd, Winchester,W.R. and Walmsley,J.A. (1994) Conformation, hydrogen bonding and aggregate formation of guanosine 5′-monophosphate and guanosine in dimethylsulfoxide. Nucleic Acids Res., 22, 5128-5134.
30. Ornstein,R.L. (1978) An optimized potential function for the calculation of nucleic acid interaction energies. I. Base stacking. Biopolymers, 17, 2341-2360.
31. Seidel,C.A.M., Schulz,A. and Sauer,M.H.M. (1996) Nucleobase-specific quenching of fluorescent dyes. 1. nucleobase one-electron redox potentials and their correlation with static and dynamic quenching efficiencies. J. Phys. Chem., 100, 5541-5553.
32. Steenken,S. and Jovanovic,S.V. (1997) How easily oxidizable is DNA? One-electron reduction potentials of adenosine and guanosine radicals in aqueous solution J. Am. Chem. Soc., 119, 617-618.
33. Meisenheimer,K.M. and Koch,T.H. (1997) Photocross-linking of nucleic acids to associated proteins. Crit. Rev. Biochem. Mol. Biol., 32, 101-140.
34. Ito,T. and Rokita,S.E. (2003) Excess electron transfer from an internally conjugated aromatic amine to 5-bromo-2′-deoxyuridine in DNA. J. Am. Chem. Soc., 125, 11480-11481.
35. Hole,E.O., Nelson,W.H., Close,D.M. and Sagstuen,E. (1987) ESR and ENDOR study of the guanine cation: Secondary product in 5′-dGMP. J. Chem. Phys., 86, 5218-5219.