SOS-dependent A→G transitions induced by hydroxyl radical generating system hypoxanthine/xanthine oxidase/Fe3+/EDTA are accompanied by the increase of Fapy-adenine content in M13 mp18 phage DNA

Mutation Research - DNA Repair

Volumn 434, Issue 1, 1999, Pages 41-52

  Gra̧ziewicz, Maria Anna ^a   Zastawny, Tomasz Hubert ^b   Oliński, Ryszard ^b   Tudek, Barbara ^a  

^a INSTITUTE OF BIOCHEMISTRY AND BIOPHYSICS   (Poland)

^b NICOLAUS COPERNICUS UNIVERSITY   (Poland)

Author keywords

DNA damage; Fapy adenine; Fapy guanine; Hydroxyl radical; Hypoxanthine xanthine oxidase; Mutations

Indexed keywords

BACTERIOPHAGE DNA; EDETIC ACID; HYDROXYL RADICAL; HYPOXANTHINE; SINGLE STRANDED DNA; XANTHINE OXIDASE; 4,6 DIAMINO 5 N FORMAMIDOPYRIMIDINE; 4,6-DIAMINO-5-N-FORMAMIDOPYRIMIDINE; FERRIC ION; PYRIMIDINE DERIVATIVE; VIRUS DNA;

ARTICLE; BACTERIOPHAGE M13; CELL SURVIVAL; DNA DETERMINATION; DNA REPAIR; ESCHERICHIA COLI; GAS CHROMATOGRAPHY; ION MONITORING; MASS SPECTROMETRY; MUTATION RATE; NUCLEIC ACID BASE SUBSTITUTION; PRIORITY JOURNAL; CHEMISTRY; DNA DAMAGE; DRUG EFFECT; GENETICS; GROWTH, DEVELOPMENT AND AGING; METABOLISM; MOLECULAR GENETICS; MUTAGENESIS; MUTATION; NUCLEOTIDE SEQUENCE; OXIDATIVE STRESS; PHYSIOLOGY; POINT MUTATION; VIRUS GENE;

BACTERIOPHAGE M13; BASE SEQUENCE; DNA DAMAGE; DNA, SINGLE-STRANDED; DNA, VIRAL; EDETIC ACID; FERRIC COMPOUNDS; GENES, VIRAL; HYDROXYL RADICAL; HYPOXANTHINE; MOLECULAR SEQUENCE DATA; MUTAGENESIS; MUTATION; OXIDATIVE STRESS; POINT MUTATION; PYRIMIDINES; SOS RESPONSE (GENETICS); XANTHINE OXIDASE;

EID: 0242677926     PISSN: 09218777     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0921-8777(99)00012-9     Document Type: Article

References (44)

1. Harman D. The aging process. Proc. Natl. Acad. Sci. USA. 78:1981;7124-7128.
2. C. von Sonntag, The Chemical Basis of Radiation Biology, Taylor & Francis, New York, 1987.
3. Shibutani S., Takeshita M., Grollman A.P. Insertion of specific bases during DNA synthesis past the oxidation-damaged base 8-oxoG. Nature. 349:1991;431-434.
4. Purmal A.A., Kow Y.W., Wallace S.S. Major oxidative products of cytosine, 5-hydroxycytosine and 5-hydroxyuracil, exhibit sequence context-dependent mispairing in vitro. Nucleic Acids Res. 22:1994;72-78.
5. Kasai H., Iida A., Yamaizumi Z., Nishimura S., Tanooka H. 5-Formyldeoxyuridine: a new type of DNA damage induced by ionising radiation and its mutagenicity to Salmonella strain TA102. Mutat. Res. 243:1990;249-253.
6. Kamiya H., Kasai H. Effects of sequence context on misincorporation of nucleotides opposite 2-hydroxyadenine. FEBS Lett. 391:1996;113-116.
7. Moriya M. Single-stranded shuttle phagemid for mutagenesis studies in mammalian cells: 8-oxoguanine in DNA induces targeted G:C→T:A transversion in simian kidney cells. Proc. Natl. Acad. Sci. USA. 90:1993;1122-1126.
8. Weitzman S.A., Turk U.W., Milkowski D.H., Kozlowski K. Free radical adducts induce alterations in DNA cytosine methylation. Proc. Natl. Acad. Sci. USA. 91:1994;1261-1264.
9. Guschlbauer W., Duplaa A.-M., Guy A., Teoule R., Fazakerley G.V. Structure and in vitro replication of DNA templates containing 7,8-dihydro-8-oxoadenine. Nucleic Acids Res. 19:1991;1753-1758.
10. Shibutani S., Bodepudi V., Johnson F., Grollman A.P. Translesional synthesis on DNA templates containing 8-oxo-7,8-dihydroxyadenosine. Biochemistry. 32:1993;4615-4621.
11. Wood M.L., Esteve A., Morningstar M.L., Kuziemko G.M., Essigmann J.M. Genetic effects of oxidative DNA damage: comparative mutagenesis of 7,8-dihydro-8 oxoguanine and 7,8-dihydro-8-oxoadenine in Eschericha coli. Nucleic Acids Res. 20:1992;6023-6032.
12. Kamiya H., Miura H., Murata-Kamiya N., Ischikawa H., Sakaguchi T., Inoue H., Sasaki T., Masutani C., Hanaoka F., Nishimura S., Ohtsuka E. 8-Hydroxyadenine (7,8-dihydro-8-oxoadenine) induces misincorporation in in vitro DNA synthesis and mutations in NIH3T3 cells. Nucleic Acids Res. 23:1995;2893-2899.
13. Rouet P., Essigman J.M. Possible role for thymine glycol in the selective inhibition of DNA synthesis on oxidised DNA templates. Cancer Res. 45:1985;6113-6118.
14. Wang D., Kreutzer D.A., Essigmann J.M. Mutagenicity and repair of oxidative DNA damage: insight from studies using defined lesions. Mutat. Res. 400:1998;99-115.
15. Dizdaroglu M. Oxidative damage to DNA in mammalian chromatin. Mutat. Res. 275:1992;331-342.
16. Dizdaroglu M. Chemical determination of oxidative DNA damage by gas chromatography-mass spectrometry. Methods Enzymol. 234:1994;3-16.
17. Olinski R., Zastawny T., Budzbon J., Skokowski J., Zegarski W., Dizdaroglu M. DNA base modifications in chromatin of human cancerous tissues. FEBS Lett. 309:1992;193-198.
18. Boiteux S., Gajewski E., Laval J., Dizdaroglu M. Substrate specificity of the Escherichia coli Fpg protein (formamidopyrimidine DNA glycosylase): excision of purine lesions in DNA produced by ionising radiation or photosensitisation. Biochemistry. 31:1992;106-110.
19. Karakaya A., Jaruga P., Bohr V.A., Grollmann A.P., Dizdaroglu M. Kinetics of excision of purine lesions from DNA by Escherichia coli Fpg protein. Nucleic Acids Res. 25:1997;474-479.
20. Karahalil B., Girard P.M., Boiteux S., Dizdaroglu M. Substrate specificity of the OGG1 protein of Saccharomyces cerevisiae: excision of guanine lesions produced in DNA by ionising radiation or hydrogen peroxide/metal ion-generated free radicals. Nucleic Acids Res. 26:1998;1228-1232.
21. O'Connor T.R., Boiteux S., Laval J. Ring-opened 7-methylguanine residues in DNA are a block to in vitro DNA synthesis. Nucleic Acids Res. 16:1988;5879-5894.
22. Tudek B., Boiteux S., Laval J. Biological properties of imidazole ring-opened N7 methylguanine in M13 mp18 phage DNA. Nucleic Acids Res. 20:1992;3070-3084.
23. J.A. Haines, C.B. Reese, J. Lord Todd, The methylation of guanosine and related compounds with diazomethane, J. Chem. Soc. (1962) 5281-5288.
24. Lawley P.D., Brookes P. Methylation of adenine in deoxyadenylic acid or deoxyribonucleic acid at N-7. Biochem. J. 92:1964;19c-20c.
25. Aruoma O.I., Halliwell B., Dizdaroglu M. Iron ion-dependent modification of bases in DNA by the superoxide radical-generating system hypoxanthine/xanthine oxidase. J. Biol. Chem. 264:1989;13024-13028.
26. Messing J. New M13 vectors for cloning. Methods Enzymol. 101:1983;20-78.
27. J. Sambrook, E.F. Fritsch, T. Maniatis, Molecular Cloning: A Laboratory Manual, 2nd edn., Cold Spring Laboratory Press, Cold Spring Harbor, New York, 1989.
28. Djuric Z., Heilbrun L.K., Reading B.A., Broomer A., Veleriote F.A., Martino S. Effects of a low-fat diet on levels of oxidative damage to DNA in human peripheral nucleated blood cells. J. Natl. Cancer Inst. 83:1991;766-769.
29. Feig D.I., Loeb L.A. Mechanisms of mutation by oxidative DNA damage: reduced fidelity of mammalian DNA polymerase β Biochemistry. 32:1993;4466-4473.
30. Kunkel T.A. Mutational specificity of depurination. Proc. Natl. Acad. Sci. USA. 81:1984;1494-1498.
31. Tudek B., Laval J., Boiteux S. SOS-independent mutagenesis in lacZ induced by methylene blue plus visible light. Mol. Gen. Genet. 236:1993;433-439.
32. Mc Bride T.J., Schneider J.E., Floyd R.A., Loeb L.A. Mutations induced by methylene blue plus light in single-stranded M13 mp2. Proc. Natl. Acad. Sci. USA. 89:1992;6866-6870.
33. Mc Bride T.J., Preston B.D., Loeb L.A. Mutagenic spectrum resulting from DNA damage by oxygen radicals. Biochemistry. 30:1991;207-213.
34. Tkeshelashvili L.K., Mc Bride T.J., Spence K., Loeb L.A. Mutation spectrum of copper-induced DNA damage. J. Biol. Chem. 266:1991;6401-6406.
35. Reid T.M., Loeb L.A. Mutagenic specificity of oxygen radicals produced by human leukemia cells. Cancer Res. 52:1992;1082-1086.
36. Hayes R.C., Petrullo L.A., Huang H., Wallace S.S., Le Clerc J.E. Oxidative damage in DNA: lack of mutagenicity by thymine glycol lesions. J. Mol. Biol. 201:1988;239-246.
37. Braun J.E.F., Wanamarta A.H., Westmijze E.J., Wjentes N.M., Wjiker C.A., Lafleur M.V.M., Retel J. Influence of nucleotide excision repair of Escherichia coli on radiation induced mutagenesis of double-stranded M13 DNA. Mutat. Res. 384:1997;45-53.
38. Murata-Kamiya N., Kamiya H., Kaji H., Kasai H. Mutational specificity of glyoxal, a product of DNA oxidation, in the lacI gene of the wild-type Eschericha coli W3110. Mutat. Res. 377:1997;255-262.
39. Murata-Kamiya N., Kamiya H., Iwamoto N., Kasai H. Formation of a mutagen, glyoxal, from DNA treated with oxygen free radicals. Carcinogenesis. 16:1995;2251-2253.
40. Douki T., Delatour T., Bianchini F., Cadet J. Observation and prevention of an artefactual formation of oxidised DNA bases and nucleosides in the GC-EIMS method. Carcinogenesis. 17:1996;347-353.
41. Douki T., Martini R., Ravanat J.L., Turesky R.J., Cadet J. Measurement of 2,6 diamino-4-hydroxy-5-formamidopyrimidine and 8-oxo-7,8 dihydroguanine in isolated DNA exposed to gamma radiation in aqueous solution. Carcinogenesis. 18:1997;2385-2391.
42. Kamiya H., Kasai H. Formation of 2-hydroxydeoxyadenosine triphosphate, and oxidatively damaged nucleotide and its incorporation by DNA polymerases. J. Biol. Chem. 270:1995;19446-19450.
43. Boiteux S., Belleney J., Roques B.P., Laval J. Two rotameric forms of open ring 7-methylguanine are present in alkylated polynucleotides. Nucleic Acids Res. 12:1984;5429-5439.
44. Tudek B., VanZeeland A.A., Kusmierek J.T., Laval J. Activity of Escherichia coli DNA glycosylases on DNA damaged by methylating and ethylating agents and influence of 3-substituted adenine derivatives. Mutat. Res. 407:1998;169-176.