Formation of 8-Hydroxyguanine by Oxidative DNA Damage, Its Repair and Its Mutagenic Effects

  • H. Kasai
  • S. Nishimura
Chapter
Part of the Advances in Mutagenesis Research book series (MUTAGENESIS, volume 4)

Abstract

In 1982 the analysis of DNA adducts was carried out, particularly guanine adducts, as one approach to the identification of direct-acting mutagens present in broiled foods and environmental materials. On analysis of adduct formation by heated glucose, as a model of broiled foods, glyoxal-Gua and 8-hydroxy-Gua (oh8Gua)1 adducts were detected as major products (Kasai, et al. 1984a; Fig. 1).

Keywords

Endonuclease Activity Potassium Bromate Thymine Glycol Human Polymorphonuclear Neutrophil Ferric Nitrilotriacetate 
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References

  1. Adelman R, Saul RL, Ames BN (1988) Oxidative damage to DNA: relation to species metabolic rate and life span. Proc Natl Acad Sci USA 85:2706–2708PubMedCrossRefGoogle Scholar
  2. Aida M, Nishimura S (1987) An ab initio molecular orbital study on the characteristics of 8-hydroxyguanine. Mutat Res 192:83–89PubMedCrossRefGoogle Scholar
  3. Basu AK, Loechler EL, Leadon SA, Essigmann JM (1989) Genetic effects of thymine glycol; site- specific mutagenesis and molecular modeling studies. Proc Natl Acad Sci USA 86:7677–7681PubMedCrossRefGoogle Scholar
  4. Cabrera M, Nghiem Y, Miller JH (1988) mut M, a second mutator locus inEscherichia coli that generates G ● C→T ● A transversions. J Bacteriol 170:5405–5407PubMedGoogle Scholar
  5. Cheng KC, Cahill DS, Kasai H, Nishimura S, Loeb LA (1992) 8-Hydroxyguanine, an abundant form of oxidative DNA damage, causes G → T and A → C substitutions. J Biol Chem 267: 166–172PubMedGoogle Scholar
  6. Chung MH, Kasai H, Jones DS, Inoue H, Ishikawa H, Ohtsuka E, Nishimura S (1991a) An endonuclease activity of Escherichia coli that specifically removes 8-hydroxyguanine residues from DNA. Mutat Res 254:1–12PubMedGoogle Scholar
  7. Chung MH, Kim HS, Ohtsuka E, Kasai H, Yamamoto F, Nishimura S (1991b) An endonuclease activity in human polymorphonuclear neutrophils that removes 8-hydroxyguanine residues from DNA. Biochem Biophys Res Commun 178:1422–1478CrossRefGoogle Scholar
  8. Culp SJ, Cho BP, Kadlubar FF, Evans FE (1989) Structural and conformational analyses of 8-hydroxy-2’-deoxyguanosine. Chem Res Toxicol 2:416–422PubMedCrossRefGoogle Scholar
  9. Demple B, Johnson A, Fung D (1986) Exonuclease III and endonuclease IV remove 3 blocks from DNA synthesis primers in H202-damagedEscherichia coli. Proc Natl Acad Sci USA 83:7731–7735PubMedCrossRefGoogle Scholar
  10. Diuric Z, Potter DW (1990) Oxidative DNA damage by 1.6-dinitropyrene in vivo. Proc 81st Annu Meet AACR 31:146Google Scholar
  11. Dizdaroglu M (1985) Formation of an 8-hydroxyguanine moiety in deoxyribonucleic acid on γ-irradiation in aqueous solution. Biochemistry 24:4476–4481PubMedCrossRefGoogle Scholar
  12. Fiala ES, Conaway CC, Mathis JE (1989) Oxidative DNA and RNA damage in the liver of Sprague-Dawley rats treated with the hepatocarcinogen 2-nitropropane. Cancer Res 49:5518–5522PubMedGoogle Scholar
  13. Floyd RA, Watson J J, Wong PK, Altmiller DH, Rickard RC (1986) Hydroxyl free radical adduct of deoxyguanosine: sensitive detection and mechanisms of formation. Free Rad Res Commun 1:163–172CrossRefGoogle Scholar
  14. Fraga CG, Shigenaga MK, Park JW, Degan P, Ames BN (1990) Oxidative damage to DNA during aging:8-hydroxy-2’-deoxyguanosine in rat organ DNA and urine. Proc Natl Acad Sci USA 87:4533–4537PubMedCrossRefGoogle Scholar
  15. Hayakawa M, Ogawa T, Sugiyama S, Tanaka M, Ozawa T (1991a) Massive conversion of guanosine to 8-hydroxyguanosine in mouse liver mitochondrial DNA by administration of azidothymidine. Biochem Biophys Res Commun 176:87–93PubMedCrossRefGoogle Scholar
  16. Hayakawa M, Torii K, Sugiyama S, Tanaka M, Ozawa T (1991b) Age-associated accumulation of 8-hydroxydeoxyguanosine in mitochondrial DNA of human diaphragm. Biochem Biophys Res Commun 179:1023–1029PubMedCrossRefGoogle Scholar
  17. Hinrichsen LI, Floyd RA, Sudilovsky O (1990) Is 8-hydroxydeoxyguanosine a mediator of carcinogenesis by a choline-devoid diet in the rat liver. Carcinogenesis, 11:1879–1881PubMedCrossRefGoogle Scholar
  18. Hollstein M, Sidransky D, Vogelstein B, Harris CC (1991) p53 Mutations in human cancers. Science 253:49–53PubMedCrossRefGoogle Scholar
  19. Kasai H, Nishimura S (1983) Hydroxylation of the C-8 position of deoxyguanosine by reducing agents in the presence of oxygen. Nucl Acids Res Symp Ser 12:165–167Google Scholar
  20. Kasai H, Nishimura S (1984a) Hydroxylation of deoxyguanosine at the C-8 position by ascorbic acid and other reducing agents. Nucl Acids Res 12:2137–2145PubMedCrossRefGoogle Scholar
  21. Kasai H, Nishimura S (1984b) DNA damage induced by asbestos in the presence of hydrogen peroxide. Gann 75:841–844PubMedGoogle Scholar
  22. Kasai H, Nishimura S (1991) Formation of 8-hydroxydeoxyguanosine in DNA by oxygen radicals and its biological significance. In:Sies H (ed) Oxidative stress, oxidant and antioxidants. Academic Press, pp 99–116Google Scholar
  23. Kasai H, Hayami H, Yamaizumi Z, Saito H, Nishimura S (1984a) Detection and identification of mutagens and carcinogens as their adducts with guanosine derivatives. Nucl Acids Res 12:2127–2136PubMedCrossRefGoogle Scholar
  24. Kasai H, Tanooka H, Nishimura S (1984b) Formation of 8-hydroxyguanine residues in DNA by X-irradiation. Gann 75:1037–1039PubMedGoogle Scholar
  25. Kasai H, Crain PF, Kuchino Y, Nishimura S, Ootsuyama A, Tanooka H (1986) Formation of 8-hydroxyguanine moiety in cellular DNA by agents producing oxygen radicals and evidence for its repair. Carcinogenesis 7:1849–1851PubMedCrossRefGoogle Scholar
  26. Kasai H, Nishimura S, Kurokawa Y, Hayashi H (1987a) Oral administration of the renal carcinogen, potassium bromate, specifically produces 8-hydroxydeoxyguanosine in rat target organ DNA. Carcinogenesis 8:1959–1961PubMedCrossRefGoogle Scholar
  27. Kasai H, Nishimura S, Toriumi Y, Itai T, Iitaka Y (1987b) The crystal structure of 9-ethyl-8-hydroxyguanine. Bull Chem Soc Jpn 60:3799–3800CrossRefGoogle Scholar
  28. Kasai H, Okada Y, Nishimura S, Rao MS, Reddy JK (1989) Formation of 8-hydroxydeoxyguanosine in liver DNA of rats following long-term exposure to a peroxisome proliferator. Cancer Res 49:2603–2605PubMedGoogle Scholar
  29. Kasprzak KS, Hernandez L (1989) Enhancement of hydroxylation and deglycosylation of 2’-deoxyguanosine by carcinogenic nickel compounds. Cancer Res 49:5964–5968PubMedGoogle Scholar
  30. Kasprzak KS, Higinbotham K, Diwan BA, Perantoni AO, Rice JM (1990) Correlation of DNA base oxidation with the activation of K-ras oncogene in nickel-induced renal tumors. Free Rad Res Commun 9 (Suppl 1):172Google Scholar
  31. Kiyosawa H, Murata K, Aota M, Inoue H, Nakazawa K, Kasai H, Nishimura S (1989) Detection of 8-hydroxydeoxyguanosine in human lymphocyte DNA. In:Hayaishi O, Niki E, Kondo M, Yoshikawa T(eds) Medical biological and chemical aspects of free radicals. Elsevier Amsterdam, pp 1511–1512Google Scholar
  32. Kouchakdjian M, Bodepudi V, Shibutani S, Eisenberg M, Johnson F, Grollman AP, Patel DJ (1991) NMR structural studies of ionizing radiation adduct 7-hydro-8-oxydeoxyguanosine (8-oxo-7H- dG) opposite deoxyadenosine in a DNA duplex. 8-oxo-7H-dG(syn) dA(anti) alignment at lesion site. Biochemistry 30:1403–1412PubMedCrossRefGoogle Scholar
  33. Kuchino Y, Mori F, Kasai H, Inoue H, Iwai S, Miura K, Ohtsuka E, Nishimura S (1987) Misreading of DNA templates containing 8-hydroxydeoxyguanosine at the modified base and at adjacent residues. Nature 327:77–79PubMedCrossRefGoogle Scholar
  34. Laval J, Boiteux S, O’Connor TR (1990) Physiological properties and repair of apurinic/sites and imidazole ring-opened guanines in DNA. Mutat Res 233:73–79PubMedCrossRefGoogle Scholar
  35. Leanderson P, Soderkvist P, Tagesson C, Axelson O (1988) Formation of 8-hydroxydeoxyguanosine by asbestos and man made mineral fibres. Br J Ind Med 45:309–311PubMedGoogle Scholar
  36. Levy DD, Teebor GW (1991) Site directed substitution of 5-hydroxymethyluracil for thymine in replicating øX-174am3 DNA via synthesis of 5-hydroxymethyl-2’-deoxyuridine-5’-triphosphate. Nucl Acids Res 19:3337–3343PubMedCrossRefGoogle Scholar
  37. Maki H, Sekiguchi M (1992) Mut T protein specifically hydrolyzes a potent mutagenic substrate for DNA synthesis. Nature 355:273–275PubMedCrossRefGoogle Scholar
  38. Meuth M (1990) The structure of mutation in mammalian cells. Biochim Biophys Acta 1032:1–17PubMedGoogle Scholar
  39. Michaels ML, Pharm L, Cruz C, Miller JH(1991) Mut M, a protein that prevents G ●C → T ● A trans versions, is formidopyrimidine-DNA glycosylase. Nucl Acids Res 19:3629–3632PubMedCrossRefGoogle Scholar
  40. Moriya M, Ou C, Bodepudi V, Johnson F, Takeshita M, Grollman AP (1991) Site-specific mutagenesis using a gapped duplex vector: a study of translesion synthesis past 8-oxodeoxyguanosine in E. coli. Mutat Res 254:281–288PubMedGoogle Scholar
  41. Nair UJ, Floyd RA, Nair J, Bussachini V, Friesen M, Bartsch H (1987) Formation of reactive oxygen species and of 8-hydroxydeoxyguanosine in DNA in vitro with betel quid ingredients. Chem Biol Interact 63:157–169PubMedCrossRefGoogle Scholar
  42. Nakae D, Yoshiji H, Maruyama H, Kinugasa T, Denda A, Konishi Y (1990) Production of both 8-hydroxydeoxyguanosine in liver DNA and y-glutamyl-transferase-positive hepatocellular lesions in rats given a choline-deficient, L-amino acid-defined diet. Jpn J Cancer Res 81:1081–1084PubMedCrossRefGoogle Scholar
  43. Oda Y, Uesugi S, Ikehara M, Nishimura S, Kawase Y, Ishikawa H, Inoue H, Ohtsuka E (1991) NMR studies of a DNA containing 8-hydroxydeoxyguanosine. Nucl Acids Res 19:1407–1412PubMedCrossRefGoogle Scholar
  44. Richter C, Park J-W, Ames BN (1988) Normal oxidative damage to mitochondrial and nuclear DNA is extensive. Proc Natl Acad Sci USA 85:6465–6467PubMedCrossRefGoogle Scholar
  45. Rosier J A, van Peteghem CH (1989) Peroxidative in vitro metabolism of diethylstilbestrol induces formation of 8-hydroxy-2’-deoxyguanosine. Carcinogenesis 10:405–406PubMedCrossRefGoogle Scholar
  46. Shibutani S, Takeshita M, Grollman AP (1991) Insertion of specific bases during DNA synthesis past the oxidation-damaged base 8-oxodG. Nature 349:431–434PubMedCrossRefGoogle Scholar
  47. Shigenaga MK, Gimeno CJ, Ames BN (1989) Urinary 8-hydroxy-2’-deoxyguanosine as a biological marker of in vivo oxidative DNA damage. Proc Natl Acad Sci USA 86:9697–9701PubMedCrossRefGoogle Scholar
  48. Shioya M, Wakabayashi K, Yamashita K, Nagao M, Sugimura T (1989) Formation of 8-hydroxydeoxyguanosine in DNA treated with facapentaene-12 and -14. Mutat Res 226:91–94CrossRefGoogle Scholar
  49. Takagi A, Sai K, Umemura T, Hasegawa R, Kurokawa Y, Kasai H (1989) Production of 8-hydroxydeoxyguanosine in rat liver DNA by oral administration of peroxisome proliferators. Igaku no Ayumi 149:65–66Google Scholar
  50. Tchou J, Kasai H, Shibutani S, Chung MH, Laval J, Grollman AP, Nishimura S (1991) 8-Oxoguanine (8-hydroxyguanine) DNA glycosylase and its substrate specificity. Proc Natl Acad Sci USA 88:4690–4694PubMedCrossRefGoogle Scholar
  51. Umemura T, Sai K, Takagi A, Hasegawa R, Kurokawa Y (1990) Formation of 8-hydroxyguanosine (8-OH-dG) in rat kidney DNA after intraperitoneal administration of ferric nitrilotriacetate (Fe-NTA). Carcinogenesis 11:345–347PubMedCrossRefGoogle Scholar
  52. Wood ML, Dizdaroglu M, Gajewski E, Essigmann JM (1990) Mechanistic studies of ionizing radiation and oxidative mutagenesis: genetic effects of a single 8-hydroxyguanine (7-hydro-8- oxoguanine) residue inserted at a unique site in a viral genome. Biochemistry 29:7024–7032PubMedCrossRefGoogle Scholar
  53. Yamamoto F, Kasai H, Chung MH, Ohtsuka E, Hori T, Nishimura S (1992) Ubiquitous presence in mammalian cells of enzymatic activity specifically cleaving 8-hydroxyguanine containing DNA. Jpn J Cancer Res (in press)Google Scholar
  54. Yanofsky C, Cox EC, Horn V (1966) The unusual mutagenic specificity of an E. coli mutator gene. Proc Natl Acad Sci USA 55:274–281PubMedCrossRefGoogle Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 1993

Authors and Affiliations

  • H. Kasai
    • 1
  • S. Nishimura
    • 1
  1. 1.Biology DivisionNational Cancer Center Research InstituteTokyoJapan

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