A single nuclease-resistant linkage in DNA as a versatile tool for the characterization of DNA lesions: Application to the guanine oxidative lesion "g+34" generated by metalloporphyrin/KHSO5 reagent

Chemical Research in Toxicology

Volumn 25, Issue 11, 2012, Pages 2505-2512

  Tomaszewska, Agnieszka ^a   Mourgues, Sophie ^a   Guga, Piotr ^a   Nawrot, Barbara ^a   Pratviel, Geneviève ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

DINUCLEOTIDE; DNA; GUANINE; HYDANTOIN DERIVATIVE; IRON; MANGANESE; METALLOPORPHYRIN; METHYLPHOSPHONIC ACID; MONOMER; NUCLEASE; OLIGONUCLEOTIDE; PORPHYRIN;

ARTICLE; CONTROLLED STUDY; DNA DAMAGE; ISOLATION PROCEDURE; NUCLEAR MAGNETIC RESONANCE; OXIDATION; STEREOISOMERISM; SYNTHESIS;

DEOXYRIBONUCLEASES; DNA; DNA DAMAGE; GUANINE; HYDROLYSIS; MANGANESE; METALLOPORPHYRINS; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; SULFURIC ACIDS;

EID: 84869419967     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx300319y     Document Type: Article

References (32)

1. Cadet, J., Douki, T., and Ravanat, J. L. (2010) Oxidatively generated base damage to cellular DNA Free Radical Biol. Med. 49, 9-21
2. Dedon, P. C. (2008) The chemical toxicology of 2-deoxyribose oxidation in DNA Chem. Res. Toxicol. 21, 206-219
3. Delaney, J. C. and Essigmann, J. M. (2008) Biological properties of single chemical-DNA adducts: A twenty year perspective Chem. Res. Toxicol. 21, 232-252
4. Jamieson, E. R. and Lippard, S. J. (1999) Structure, recognition, and processing of cisplatin-DNA adducts Chem. Rev. 99, 2467-2498
5. Chworos, A., Coppel, Y., Dubey, I., Pratviel, G., and Meunier, B. (2001) Guanine oxidation: NMR characterization of a dehydro-guanidinohydantoin residue generated by a 2e-oxidation of d(GpT) J. Am. Chem. Soc. 123, 5867-5877
6. Seguy, C., Pratviel, G., and Meunier, B. (2001) Characterization of an oxaluric acid derivative as a guanine oxidation product Chem. Commun. 2116-2117
7. Chworos, A., Seguy, C., Pratviel, G., and Meunier, B. (2002) Characterization of the dehydro-guanidinohydantoin oxidation product of guanine in a dinucleotide Chem. Res. Toxicol. 15, 1643-1651
8. Perrier, S., Hau, J., Gasparutto, D., Cadet, J., Favier, A., and Ravanat, J. L. (2006) Characterization of lysine-guanine cross-links upon one-electron oxidation of a guanine-containing oligonucleotide in the presence of a trilysine peptide J. Am. Chem. Soc. 128, 5703-5710
9. Ye, W., Sangaiah, R., Degen, D. E., Gold, A., Jayaraj, K., Koshlap, K. M., Boysen, G., Williams, J., Tomer, K. B., and Ball, L. M. (2006) A 2-iminohydantoin from the oxidation of guanine Chem. Res. Toxicol. 19, 506-510
10. Ye, W., Sangaiah, R., Degen, D. E., Gold, A., Jayaraj, K., Koshlap, K. M., Boysen, G., Williams, J., Tomer, K. B., Mocanu, V., Dicheva, N., Parker, C. E., Schaaper, R. M., and Ball, L. M. (2009) Iminohydantoin lesion induced in DNA by peracids and other epoxidizing oxidants J. Am. Chem. Soc. 131, 6114-6123
11. Romera, C., Sabater, L., Garofalo, A., Dixon, I. M., and Pratviel, G. (2010) Interaction of cationic nickel and manganese porphyrins with the minor groove of DNA Inorg. Chem. 49, 8558-8567
12. Meunier, B., Robert, A., Pratviel, G., and Bernadou, J., Eds. (2000) Metalloporphyrins in Catalytic Oxidation and Oxidative DNA Damage, Vol. 4, Academic Press, San Diego, CA.
13. 5 to imidazolone dIz without formation of 8-oxo-dG J. Am. Chem. Soc. 120, 11548-11553
14. 5: 5,8-Dihydroxy-7,8-dihydroguanine residue as a key precursor of imidazolone and parabanic acid derivatives J. Am. Chem. Soc. 122, 2157-2167
15. Angeloff, A., Dubey, I., Pratviel, G., Bernadou, J., and Meunier, B. (2001) Characterization of a 5′-aldehyde terminus resulting from the oxidative attack at C5′ of a 2-deoxyribose on DNA Chem. Res. Toxicol. 14, 1413-1420
16. Mourgues, S., Kupan, A., Pratviel, G., and Meunier, B. (2005) Use of short duplexes for the analysis of the sequence-dependent cleavage of DNA by a chemical nuclease, a manganese porphyrin ChemBioChem 6, 2326-2335
17. Kupan, A., Sauliere, A., Broussy, S., Seguy, C., Pratviel, G., and Meunier, B. (2006) Guanine oxidation by electron transfer: one- versus two-electron oxidation mechanism ChemBioChem 7, 125-133
18. Pitié, M. and Pratviel, G. (2010) Activation of DNA carbon-hydrogen bonds by metal complexes Chem. Rev. 110, 1018-1059
19. 5 system results from a cytochrome P-450-type hydroxylation reaction J. Am. Chem. Soc. 117, 2935-2936
20. Li, L., Murthy, N. N., Telser, J., Zakharov, L. N., Yap, G. P., Rheingold, A. L., Karlin, K. D., and Rokita, S. E. (2006) Targeted guanine oxidation by a dinuclear copper(II) complex at single stranded/double stranded DNA junctions Inorg. Chem. 45, 7144-7159
21. 2/reductant in nucleoside and oligodeoxynucleotide contexts Org. Biomol. Chem. 9, 3338-3348
22. Ghude, P., Schallenberger, M. A., Fleming, A. M., Muller, J. G., and Burrows, C. J. (2011) Comparison of transition metal-mediated oxidation reactions of guanine in nucleoside and single-stranded oligodeoxynucleotide contexts Inorg. Chim. Acta 369, 240-246
23. Rokhlenko, Y., Geacintov, N. E., and Shafirovich, V. (2012) Lifetimes and reaction pathways of guanine radical cations and neutral guanine radicals in an oligonucleotide in aqueous solutions J. Am. Chem. Soc. 134, 4955-4962
24. Luo, W., Muller, J. G., Rachlin, E. M., and Burrows, C. J. (2000) Characterization of spiroiminodihydantoin as a product of one-electron oxidation of 8-oxo-7,8-dihydroguanosine Org. Lett. 2, 613-616
25. Niles, J. C., Wishnok, J. S., and Tannenbaum, S. R. (2001) Spiroiminodihydantoin is the major product of the 8-oxo-7,8-dihydroguanosine reaction with peroxynitrite in the presence of thiols and guanosine photooxidation by methylene blue Org. Lett. 3, 963-966
26. Adam, W., Arnold, M. A., Grune, M., Nau, W. M., Pischel, U., and Saha-Moller, C. R. (2002) Spiroiminodihydantoin is a major product in the photooxidation of 2′-deoxyguanosine by the triplet states and oxyl radicals generated from hydroxyacetophenone photolysis and dioxetane thermolysis Org. Lett. 4, 537-540
27. Slade, P. G., Priestley, N. D., and Sugden, K. D. (2007) Spiroiminodihydantoin as an oxo-atom transfer product of 8-oxo-2′- deoxyguanosine oxidation by chromium(V) Org. Lett. 9, 4411-4414
28. Hailer, M. K., Slade, P. G., Martin, B. D., and Sugden, K. D. (2005) Nei deficient Escherichia coli are sensitive to chromate and accumulate the oxidized guanine lesion spiroiminodihydantoin Chem. Res. Toxicol. 18, 1378-1383
29. Chworos, A., Arnaud, P., Zakrzewska, K., Guga, P., Pratviel, G., Stec, W., and Meunier, B. (2004) Comparison of the cleavage profiles of oligonucleotide duplexes with or without phosphorothioate linkages by using a chemical nuclease probe J. Biol. Inorg. Chem. 9, 374-384
30. Reynolds, M. A., Hogrefe, R. I., Jaeger, J. A., Schwartz, D. A., Riley, T. A., Marvin, W. B., Daily, W. J., Vaghefi, M. M., Beck, T. A., Knowles, S. K., Klem, R. E., and Arnold, L. J., Jr. (1996) Synthesis and thermodynamics of oligonucleotides containing chirally pure R(P) methylphosphonate linkages Nucleic Acids Res. 24, 4584-4591
31. Bernadou, J., Pratviel, G., Bennis, F., Girardet, M., and Meunier, B. (1989) Potassium monopersulfate and a water-soluble manganese porphyrin complex, [Mn(TMPyP)](OAc)5, as an efficient reagent for the oxidative cleavage of DNA Biochemistry 28, 7268-7275
32. Bernadou, J. and Meunier, B. (1998) Oxo-hydroxo tautomerism as useful mechanistic tool in oxygenation reactions catalysed by water-soluble metalloporphyrins Chem. Commun. 2167-2173