A DNA oligomer containing 2,2,4-triamino-5(2H)-oxazolone is incised by human NEIL1 and NTH1

Mutation Research - Fundamental and Molecular Mechanisms of Mutagenesis

Volumn 734, Issue 1-2, 2012, Pages 73-77

  Kino, Katsuhito ^a   Takao, Masashi ^b   Miyazawa, Hiroshi ^a   Hanaoka, Fumio ^c,d  

^a TOKUSHIMA BUNRI UNIVERSITY   (Japan)

^b TOHOKU UNIVERSITY   (Japan)

^c GAKUSHUIN UNIVERSITY   (Japan)

^d JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

Base excision repair enzyme; Guanine oxidation; Human NEIL1; Human NTH1; Oxazolone

Indexed keywords

2,2,4 TRIAMINO 5(2H) OXAZOLONE; DNA; ENZYME; NUCLEIC ACID BASE; OLIGOMER; PIPERIDINE; PROTEIN NEIL1; PROTEIN NTH1; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; ENZYME ACTIVITY; ENZYME MECHANISM; HUMAN; OXIDATION; POINT MUTATION; PRIORITY JOURNAL; PROTEIN CLEAVAGE;

DEOXYRIBONUCLEASE (PYRIMIDINE DIMER); DNA GLYCOSYLASES; GUANINE; HUMANS; OXAZOLONE; OXIDATION-REDUCTION; POINT MUTATION;

PROKARYOTA;

EID: 84862027113     PISSN: 00275107     EISSN: 09218262     Source Type: Journal    
DOI: 10.1016/j.mrfmmm.2012.03.007     Document Type: Article

References (24)

1. Bjelland S., Seeberg E. Mutagenicity, toxicity and repair of DNA base damage induced by oxidation. Mutat. Res. 2003, 531:37-80.
2. Cadet J., Berger M., Buchko G.W., Joshi P.C., Raoul S., Ravanat J.-L. 2,2-Diamino-4-[(3,5-di-O-acetyl-2-deoxy-β-D-erythro-pentofuranosyl)amino]-5-(2H)-oxazolone: a novel and predominant radical oxidation product of 3',5'-di-O-acetyl-2'-deoxyguanosine. J. Am. Chem. Soc. 1994, 116:7403-7404.
3. Buchko G.W., Cadet J., Morin B., Weinfeld M. Photooxidation of d(TpG) by riboflavin and methylene blue. Isolation and characterization of thymidylyl-(3',5')-2-amino-5-[(2-deoxy-β-D-erythro-pentofuranosyl)amino]-4H-imidazol-4-one and its primary decomposition product thymidylyl-(3',5')-2,2-diamino-4-[(2-deoxy-β -D-erythro-pentofuranosyl)amino-5(2H)-oxazolone. Nucleic Acids Res. 1995, 23:3954-3961.
4. Gasparutto D., Ravanat J.-L., Gérot O., Cadet J. Characterization and chemical stability of photooxidized oligonucleotides that contain 2,2-diamino-4-[(2-deoxy-β -D-erythro-pentofuranosyl)amino-5(2H)-oxazolone. J. Am. Chem. Soc. 1998, 120:10283-10286.
5. Luo W., Muller J.G., Burrows C.J. The pH-dependent role of superoxide in riboflavin-catalyzed photooxidation of 8-oxo-7,8-dihydroguanosine. Org. Lett. 2001, 3:2801-2804.
6. Kino K., Sugiyama H. Possible cause of G-C->C-G transversion mutation by guanine oxidation product, imidazolone. Chem. Biol. 2001, 8:369-378.
7. Tretyakova N.Y., Wishnok J.S., Tannenbaum S.R. Peroxynitrite-induced secondary oxidative lesions at guanine nucleobases: chemical stability and recognition by the Fpg DNA repair enzyme. Chem. Res. Toxicol. 2000, 13:658-664.
8. Kino K., Morikawa M., Kobayashi T., Kobayashi T., Komori R., Sei Y., Miyazawa H. The oxidation of 8-oxo-7,8-dihydroguanine by iodine. Bioorg. Med. Chem. Lett. 2010, 20:3818-3820.
9. Matter B., Malejka-Giganti D., Csallany A.S., Tretyakova N. Quantitative analysis of the oxidative DNA lesion, 2,2-diamino-4-(2-deoxy-β-D-erythro-pentofuranosyl)amino]-5(2H)-oxazolone (oxazolone), in vitro and in vivo by isotope dilution-capillary HPLC-ESI-MS/MS. Nucleic Acids Res. 2006, 34:5449-5460.
10. Duarte V., Gasparutto D., Jaquinod M., Cadet J. In vitro DNA synthesis opposite oxazolone and repair of this DNA damage using modified oligonucleotides. Nucleic Acids Res. 2000, 28:1555-1563.
11. Henderson P.T., Delaney J.C., Gu F., Tannenbaum S.R., Essigmann J.M. Oxidation of 7,8-dihydro-8-oxoguanine affords lesions that are potent sources of replication errors in vivo. Biochemistry 2002, 41:914-921.
12. Kino K., Sugasawa K., Mizuno T., Bando T., Sugiyama H., Akita M., Miyazawa H., Hanaoka F. Eukaryotic DNA polymerase alpha, beta and epsilon incorporate guanine opposite 2,2,4-triamino-5(2H)-oxazolone. ChemBioChem 2009, 10:2613-2616.
13. Friedberg E.C., Walker G.C., Siede W., Wood R.D., Schultz R.A., Ellenberger T., Repair D.N.A Mutagenesis 2006, ASM, Washington, DC. second ed.
14. Katafuchi A., Nakano T., Masaoka A., Terato H., Iwai S., Hanaoka F., Ide H. Differential specificity of human and Escherichia coli endonuclease III and VIII homologues for oxidative base lesions. J. Biol. Chem. 2004, 279:14464-14471.
15. Luo W., Muller J.G., Rachlin E.M., Burrows C.J. Characterization of hydantoin products from one-electron oxidation of 8-oxo-7,8-dihydroguanosine in a nucleoside model. Chem. Res. Toxicol. 2001, 14:927-938.
16. Kornyushyna O., Berges A.M., Muller J.G., Burrows C.J. In vitro nucleotide misinsertion opposite the oxidized guanosine lesions spiroiminodihydantoin and guanidinohydantoin and DNA synthesis past the lesions using Escherichia coli DNA polymerase I (Klenow fragment). Biochemistry 2002, 41:15304-15314.
17. Miyabe I., Zhang Q.M., Kino K., Sugiyama H., Takao M., Yasui A., Yonei S. Identification of 5-formyluracil DNA glycosylase activity of human hNTH1 protein. Nucleic Acids Res. 2002, 30:3443-3448.
18. Takao M., Kanno S., Kobayashi K., Zhang Q.M., Yonei S., van der Horst G.T., Yasui A. A back-up glycosylase in Nth1 knock-out mice is a functional Nei (endonuclease VIII) homologues. J. Biol. Chem. 2002, 277:42205-42213.
19. Hazra T.K., Izumi T., Boldogh I., Imhoff B., Kow Y.W., Jaruga P., Dizdaroglu M., Mitra S. Identification and characterization of a human DNA glycosylase for repair of modified bases in oxidatively damaged DNA. Proc. Natl. Acad. Sci. U.S.A. 2002, 99:3523-3528.
20. Hailer M.K., Slade P.G., Martin B.D., Rosenquist T.A., Sugden K.D. Recognition of the oxidized lesions spiroiminodihydantoin and guanidinohydantoin in DNA by the mammalian base excision repair glycosylases NEIL1 and NEIL2. DNA Repair 2005, 4:41-50.
21. Gasparutto D., Muller E., Boiteux S., Cadet J. Excision of the oxidatively formed 5-hydroxyhydantoin and 5-hydroxy-5-methylhydantoin pyrimidine lesions by Escherichia coli and Saccharomyces cerevisiae DNA N-glycosylases. Biochim. Biophys. Acta 2009, 1790:16-24.
22. Kino K., Sugasawa K., Sugiyama H., Miyazawa H., Hanaoka F. The base excision repair reaction of oxazolone with hOGG1. Photomed. Photobiol. 2004, 26:41-42.
23. Bruner S.D., Norman D.P., Verdine G.L. Structural basis for recognition and repair of the endogenous mutagen 8-oxoguanine in DNA. Nature 2000, 403:859-866.
24. Takao M., Zhang Q.M., Yonei S., Yasui A. Differential subcellular localization of human MutY homolog (hMYH) and the functional activity of adenine:8-oxoguanine DNA glycosylase. Nucleic Acids Res. 1999, 27:3638-3644.