Guanine sulphinate is a major stable product of photochemical oxidation of DNA 6-thioguanine by UVA irradiation

Nucleic Acids Research

Volumn 38, Issue 6, 2009, Pages 1832-1840

  Ren, Xiaolin ^a,b   Li, Feng ^a   Jeffs, Graham ^b   Zhang, Xiaohong ^a,b   Xu, Yao Zhong ^b   Karran, Peter ^a  

^a IMPERIAL CANCER RESEARCH FUND   (United Kingdom)

^b OPEN UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ASCORBIC ACID; CHEMICAL COMPOUND; DEOXYGUANOSINE; DEOXYRIBONUCLEOSIDE; GUANINE SULPHENATE; GUANINE SULPHINATE; GUANINE SULPHONATE; TIOGUANINE; UNCLASSIFIED DRUG; ARYLSULFONIC ACID DERIVATIVE; DNA; DRUG DERIVATIVE; GUANINE; GUANINE 6 SULFONATE; GUANINE-6-SULFONATE; SODIUM SULFIDE; SULFIDE;

ANTIOXIDANT ACTIVITY; ARTICLE; CHEMICAL REACTION; CONTROLLED STUDY; DNA DAMAGE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; OXIDATION REDUCTION REACTION; PHOTOOXIDATION; PRIORITY JOURNAL; ULTRAVIOLET A RADIATION; CHEMISTRY; PHOTOCHEMISTRY; RADIATION EXPOSURE; ULTRAVIOLET RADIATION;

ARYLSULFONATES; ASCORBIC ACID; DNA; GUANINE; OXIDATION-REDUCTION; PHOTOCHEMICAL PROCESSES; SULFIDES; THIOGUANINE; ULTRAVIOLET RAYS;

EID: 77951210792     PISSN: 03051048     EISSN: 13624962     Source Type: Journal    
DOI: 10.1093/nar/gkp1165     Document Type: Article

References (18)

1. Cadet, J., Sage, E. and Douki, T. (2005) Ultraviolet radiation-mediated damage to cellular DNA. Mutat. Res., 571, 3-17.
2. WHO. (1994) International Programme on Chemical Safety, Ultraviolet Radiation. World Health Organization, Geneva.
3. Elion, G.B. (1989) The purine path to chemotherapy. Science, 244, 41-47.
4. Weinshilboum, R. (2001) Thiopurine pharmacogenetics: clinical and molecular studies of thiopurine metabolism. Drug Metab. Dispos., 29, 601-605.
5. O'Donovan, P., Perrett, C., Zhang, X., Montaner, B., Xu, Y.-Z., Harwood, C.A., McGregor, J.M., Walker, S.L., Hanaoka, F. and Karran, P. (2005) Azathioprine and UVA light generate mutagenic oxidative DNA damage. Science, 309, 1871-1874.
6. Zhang, X., Jeffs, G., Ren, X., O'Donovan, P., Montaner, B., Perrett, C.M., Karran, P. and Xu, Y.-Z. (2006) Novel DNA lesions generated by the interaction between therapeutic thiopurines and UVA light. DNA Repair, 6, 344-354.
7. Cooke, M.S., Duarte, T.L., Cooper, D., Chen, J., Nandagopal, S. and Evans, M.D. (2008) Combination of azathioprine and UVA irradiation is a major source of cellular 8-oxo-7, 8-dihydro-2′-deoxyguanosine. DNA Repair, 7, 1982-1989.
8. Sies, H. (1993) Damage to plasmid DNA by singlet oxygen and its protection. Mutat. Res., 299, 183-191.
9. Montaner, B., O'Donovan, P., Reelfs, O., Perrett, C.M., Zhang, X., Xu, Y.-Z., Ren, X., Macpherson, P., Frith, D. and Karran, P. (2007) Reactive oxygen-mediated damage to a human DNA replication and repair protein. EMBO Rep., 8, 1074-1079.
10. Brem, R., Li, F. and Karran, P. (2008) Reactive oxygen species generated by thiopurine/UVA cause irreparable transcription-blocking DNA lesions. Nucleic Acids Res., 37, 1951-1961.
11. Penn, I. (1994) The problem of cancer in transplant patients: an overview. Transplant. Sci., 4, 23-32.
12. Perrett, C.M., Walker, S.L., O'Donovan, P., Warwick, J., Harwood, C.A., Karran, P. and McGregor, J. (2008) Azathioprine treatment sensitizes human skin to ultraviolet A radiation. Br. J. Dermatol., 159, 198-204.
13. Driscoll, C.M.H., Campbell, J.I., Pearson, A.J., Grainger, K.J.-L., Dean, S.F. and Clark, I.E. (2002) National Radiological Protection Board, Chilton, Didcot, Oxon. OX11 0RQ, pp. 1-14.
14. Sies, H. and Stahl, W. (2004) Nutritional protection against skin damage from sunlight. Annu. Rev. Nutr., 24, 173-200.
15. Doerr, I.L., Wempen, I., Clarke, D.A. and Fox, J.J. (1961) Thiation of nucleosides III. Oxidation of 6-mercaptopurines. J. Org. Chem., 26, 3401-3409.
16. Abraham, R.T., Benson, L.M. and Jardine, I. (1983) Synthesis and pH-dependent stability of purine-6-sulfenic acid, a putative reactive metabolite of 6-thiopurine. J. Med. Chem., 26, 1523-1526.
17. Garssen, J., van Steeg, H., de Gruijl, F., de Boer, J., van der Horst, G.T.J., van Kranen, H., van Loveren, H., van Dijk, M., Fluitman, A., Weeda, G. et al. (2000) Transcription-coupled and global genome repair differentially influence UV-B-induced acute skin effects and systemic immunosuppression. J. Immunol., 164, 6199-6205.
18. Daehn, I. and Karran, P. (2008) Immune effector cells produce lethal DNA damage in cells treated with a thiopurine. Cancer Res., 69, 2393-2399.