DNA-polyamine cross-links generated upon one electron oxidation of DNA

Chemical Research in Toxicology

Volumn 27, Issue 6, 2014, Pages 1011-1018

  Silerme, Stéphanie ^a   Bobyk, Laure ^a   Taverna Porro, Marisa ^a,c   Cuier, Camille ^a   Saint Pierre, Christine ^a   Ravanat, Jean Luc ^a,b  

^a UNIV GRENOBLE ALPES   (France)

^b CEA GRENOBLE   (France)

^c JOHNS HOPKINS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; DEOXYGUANOSINE; DOUBLE STRANDED DNA; GUANINE; POLYAMINE; PUTRESCINE; SPERMIDINE; SPERMINE; CALF THYMUS DNA; CROSS LINKING REAGENT; DNA;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DNA ADDUCT; DNA CROSS LINKING; ELECTROSPRAY MASS SPECTROMETRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIMIT OF QUANTITATION; NUCLEOPHILICITY; ONE ELECTRON OXIDATION REACTION; PHOTOSENSITIZATION; PROTEIN DNA INTERACTION; RADICAL REACTION; TANDEM MASS SPECTROMETRY; ANIMAL; BOVINE; CHEMISTRY; ELECTRON; ISOLATION AND PURIFICATION; OXIDATION REDUCTION REACTION;

ANIMALS; CATTLE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CROSS-LINKING REAGENTS; DNA; ELECTRONS; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; POLYAMINES; TANDEM MASS SPECTROMETRY;

EID: 84902477486     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx500063d     Document Type: Article

References (38)

1. Lindahl, T. (1993) Instability and decay of the primary structure of DNA Nature 362, 709-715 (Pubitemid 23125973)
2. Cooke, M. S., Evans, M. D., Dizdaroglu, M., and Lunec, J. (2003) Oxidative DNA damage: mechanisms, mutation, and disease FASEB J. 17, 1195-1214 (Pubitemid 36775767)
3. Kanvah, S., Joseph, J., Schuster, G. B., Barnett, R. N., Cleveland, C. L., and Landman, U. (2010) Oxidation of DNA: damage to nucleobases Acc. Chem. Res. 43, 280-287
4. Foote, C. S. (1991) Definition of type I and type II photosensitized oxidation Photochem. Photobiol. 54, 659
5. Pratviel, G. and Meunier, B. (2006) Guanine oxidation: one- and two-electron reactions Chem. - Eur. J. 12, 6018-6030 (Pubitemid 44231026)
6. Cadet, J., Douki, T., and Ravanat, J. L. (2008) Oxidatively generated damage to the guanine moiety of DNA: Mechanistic aspects and formation in cells Acc. Chem. Res. 41, 1075-1083
7. Giese, B. (2002) Electron transfer in DNA Curr. Opin. Chem. Biol. 6, 612-618 (Pubitemid 35284192)
8. Kasai, H., Yamaizumi, Z., Berger, M., and Cadet, J. (1992) Photosensitized formation of 7,8-dihydro-8-oxo-2′-deoxyguanosine (8-hydroxy-2′-deoxyguanosine) in DNA by riboflavin: a non singlet oxygen mediated mechanism J. Am. Chem. Soc. 114, 9692-9694
9. Buchko, G. W., Cadet, J., Ravanat, J.-L., and Labataille, P. (1993) Isolation and characterization of a new product produced by ionizing irradiation and type I photosensitization of 2′-deoxyguanosine in oxygen-saturated aqueous solution: (2S)-2,5′-anhydro-1-(2-deoxy-α-D-erythro- pentofuranosyl)-5-guanidinylidene-2-hydroxy-4-oxoimidazolidine Int. J. Radiat. Biol. 63, 669-676 (Pubitemid 23186537)
10. Morin, B. and Cadet, J. (1995) Type I benzophenone-mediated nucleophilic reaction of 5′-amino-2′,5′-dideoxyguanosine. A model system for the investigation of photosensitized formation of DNA-protein cross-links Chem. Res. Toxicol. 8, 792-799
11. Morin, B. and Cadet, J. (1995) Chemical aspects of the benzophenone-photosensitized formation of two lysine-2′-deoxyguanosine cross-links J. Am. Chem. Soc. 117, 12408-12415
12. Morin, B. and Cadet, J. (1994) Benzophenone photosensitization of 2′-deoxyguanosine: characterization of the 2R and 2S diastereoisomers of 1-(2-deoxy-β-D- erythro -pentofuranosyl)- 2-methoxy-4,5-imidazolidinedione. A model system for the investigation of photosensitized formation of DNA-protein crosslinks Photochem. Photobiol. 60, 102-109 (Pubitemid 2129981)
13. Cadet, J., Douki, T., and Ravanat, J.-L. (2006) One-electron oxidation of DNA and inflammation processes Nat. Chem. Biol. 2, 348-349 (Pubitemid 43941027)
14. 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 (Pubitemid 43724372)
15. Madugundu, G. S., Wagner, J. R., Cadet, J., Kropachev, K., Yun, B. H., Geacintov, N. E., and Shafirovich, V. (2013) Generation of guanine-thymine cross-links in human cells by one-electron oxidation mechanisms Chem. Res. Toxicol. 26, 1031-1033
16. 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
17. Sarhan, S. and Seiler, N. (1989) On the subcellular localization of the polyamines Biol. Chem. Hoppe. Seyler 370, 1279-1284 (Pubitemid 20063281)
18. Gerner, E. W. and Meyskens, F. L. (2004) Polyamines and cancer: Old molecules, new understanding Nat. Rev. Cancer 4, 781-792 (Pubitemid 39331150)
19. Saminathan, M., Thomas, T., Shirahata, A., Pillai, C. K., and Thomas, T. J. (2002) Polyamine structural effects on the induction and stabilization of liquid crystalline DNA: potential applications to DNA packaging, gene therapy and polyamine therapeutics Nucleic Acids Res. 30, 3722-3731 (Pubitemid 35012444)
20. Bachrach, U. (2004) Polyamines and cancer: Minireview article Amino Acids 26, 307-309 (Pubitemid 39093131)
21. Moulinoux, J. P., Quemener, V., Havouis, R., Guille, F., Martin, C., and Seiler, N. (1991) Accumulation of polyamine analogs in red blood cells: a potential index of tumor proliferation rate Anticancer Res. 11, 2143-2146
22. Moulinoux, J. P., Quemener, V., and Khan, N. A. (1991) Biological significance of circulating polyamines in oncology Cell. Mol. Biol. 37, 773-783
23. Pegg, A. E. and Hu, R. H. (1995) Effect of polyamine analogues and inhibition of polyamine oxidase on spermidine/spermine N1-acetyltransferase activity and cell proliferation Cancer Lett. 95, 247-252
24. Demoor-Goldschmidt, C. and Raynard, B. (2009) How can we integrate nutritional support in medical oncology? Bull. Cancer 96, 665-675
25. Kasai, H., Yamaizumi, Z., Berger, M., and Cadet, J. (1992) Photosensitized formation of 7,8-dihydro-8-oxo-2′-deoxyguanosine (8-hydroxy-2′-deoxyguanosine) in DNA by riboflavin-a nonsinglet oxygen mediated reaction J. Am. Chem. Soc. 114, 9692-9694
26. Ravanat, J.-L., Douki, T., Duez, P., Gremaud, E., Herbert, K., Hofer, T., Lasserre, L., Saint-Pierre, C., Favier, A., and Cadet, J. (2002) Cellular background level of 8-oxo-7,8-dihydro-2′-deoxyguanosine: an isotope based method to evaluate artefactual oxidation of DNA during its extraction and subsequent work-up Carcinogenesis 23, 1911-1918 (Pubitemid 35355940)
27. Frelon, S., Douki, T., Ravanat, J.-L., Pouget, J.-P., Tornabene, C., and Cadet, J. (2000) High performance liquid chromatography-tandem mass spectrometry for the measurement of radiation-induced base damage to isolated and cellular DNA Chem. Res. Toxicol. 13, 1002-1010
28. Ravanat, J.-L., Duretz, B., Guiller, A., Douki, T., and Cadet, J. (1998) Isotope dilution high-performance liquid chromatography-electrospray tandem mass spectrometry assay for the measurement of 8-oxo-7,8-dihydro-2′- deoxyguanosine in biological samples J. Chromatogr., B 715, 349-356
29. Munzel, M., Szeibert, C., Glas, A. F., Globisch, D., and Carell, T. (2011) Discovery and synthesis of new UV-induced intrastrand C(4-8)G and G(8-4)C photolesions J. Am. Chem. Soc. 133, 5186-5189
30. Johnson, F., Huang, C. Y., and Yu, P. L. (1994) Synthetic and oxidative studies on 8-(arylamino)-2′-deoxyguanosine and -guanosine derivatives Environ. Health Perspect. 102 (Suppl 6) 143-149 (Pubitemid 24364895)
31. Regulusqq, P., Spessotto, S., Gateau, M., Cadet, J., Favier, A., and Ravanat, J.-L. (2004) Detection of new radiation-induced DNA lesions by liquid chromatography coupled to tandem mass spectrometry Rapid Commun. Mass Spectrom. 18, 2223-2228 (Pubitemid 39297357)
32. Cadet, J. and Weinfeld, M. (1993) Detecting DNA damage Anal. Chem. 65, 675A-682A
33. Ravanat, J. L., Duretz, B., Guiller, A., Douki, T., and Cadet, J. (1998) Isotope dilution high-performance liquid chromatography-electrospray tandem mass spectrometry assay for the measurement of 8-oxo-7,8-dihydro-2′- deoxyguanosine in biological samples J. Chromatogr., B 715, 349-356
34. Douki, T., Bretonniere, Y., and Cadet, J. (2000) Protection against radiation-induced degradation of DNA bases by polyamines Radiat. Res. 153, 29-35 (Pubitemid 30117081)
35. Deng, H., Bloomfield, V. A., Benevides, J. M., and Thomas, G. J., Jr. (2000) Structural basis of polyamine-DNA recognition: spermidine and spermine interactions with genomic B-DNAs of different GC content probed by Raman spectroscopy Nucleic Acids Res. 28, 3379-3385 (Pubitemid 30662304)
36. Johansen, M. E., Muller, J. G., Xu, X., and Burrows, C. J. (2005) Oxidatively induced DNA-protein cross-linking between single-stranded binding protein and oligodeoxynucleotides containing 8-oxo-7,8-dihydro-2′- deoxyguanosine Biochemistry 44, 5660-5671 (Pubitemid 40528449)
37. Xu, X., Muller, J. G., Ye, Y., and Burrows, C. J. (2008) DNA-protein cross-links between guanine and lysine depend on the mechanism of oxidation for formation of C5 vs C8 guanosine adducts J. Am. Chem. Soc. 130, 703-709 (Pubitemid 351455584)
38. Barker, S., Weinfeld, M., and Murray, D. (2005) DNA-protein crosslinks: their induction, repair, and biological consequences Mutat. Res. 589, 111-135 (Pubitemid 40431691)