Artifacts associated with the measurement of oxidized DNA bases

Environmental Health Perspectives

Volumn 105, Issue 10, 1997, Pages 1034-1039

  Cadet, Jean ^a   Douki, Thierry ^a   Ravanat, Jean Luc ^a  

^a CEA GRENOBLE   (France)

Author keywords

DNA base damage; DNA repair enzymes; Oxidative lesions

Indexed keywords

CELL DNA; DNA BASE; GUANINE DERIVATIVE; PHOSPHORUS 32; POLYDEOXYRIBONUCLEOTIDE SYNTHASE;

ARTIFACT; DERIVATIZATION; DNA DAMAGE; ELECTROCHEMICAL DETECTION; EXTRACTION; GAS CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; MEASUREMENT; OXIDATION; OXIDATIVE STRESS; PRIORITY JOURNAL; REVIEW;

EID: 0031428488     PISSN: 00916765     EISSN: None     Source Type: Journal    
DOI: 10.2307/3433836     Document Type: Review

References (83)

1. Ames BN, Shigenaga MK, Hagen TM. Oxidants, antioxidants, and degenerative diseases of aging. Proc Natl Acad Sci USA 90:7915-7922 (1993).
2. Ames BN, Gold LS, Willett WC. The causes and prevention of cancer. Proc Natl Acad Sci USA 92:5258-5265 (1995).
3. Loft S, Poulsen HE. Cancer risk and oxidative DNA damage in man. J Mol Med 74:297-312 (1996).
4. Cadet J. DNA damage caused by oxidation, deamination, ultraviolet radiation and photoexcited psoralens. In: DNA Adducts: Identification and Biological Significance (Hemminki K, Dipple A, Shuker DEG, Kadlubar FF, Segerbäck D, Bartsch H, eds). IARC Scientific Publications No 125. Lyon:International Agency for Research on Cancer, 1994;245-276.
5. Cadet J, Berger M, Douki T, Ravanat J-L. Oxidative damage to DNA: formation, measurement and biological significance. Rev Biochem Physiol Pharmacol 131:1-87 (1997).
6. Basu AK, Loechler EL, Leadon SA, Essigmann JM. Genetic effects of thymine glycols: site specific mutagenesis and molecular modeling studies. Proc Natl Acad Sci USA 86:7677-7681 (1989).
7. Cheng KC, Cahill DS, Kasai H, Nishimura S, Loeb L. 8-Hydroxyguanine, an abundant form of oxidative damage, causes G→T and G→A substitutions. J Biol Chem 267:166-172 (1992).
8. Wood LM, Esteve A, Morningstar ML, Kuziemko GM, Essigmann JM. Genetic effects of oxidative DNA damage: comparative mutagenesis of 7,8-dihydro-8-oxoguanine and 7,8-dihydro-8-oxoadenine in Escherichia coli. Nucleic Acids Res 20:6023-6032 (1992).
9. Purmal AA, Kow Wah Y, Wallace SS. Major oxidative products of cytosine, 5-hydroxycytosine and 5-hydroxyuracil, exhibit sequence context-dependent mispairing in vivo. Nucleic Acids Res 22:72-78 (1994).
10. Grollman AP, Moriya M. Mutagenesis by 8-oxoguanine: an enemy within. Trends Genet 9:246-249 (1993).
11. Breimer LH, Lindahl T. DNA glycosylase activities of thymine residues damaged by ring saturation, fragmentation, or ring contraction, are functions of endonuclease III in Escherichia coli. J Biol Chem 259:5543-5548 (1984).
12. Boiteux S, Gajewski E, Laval J, Dizdaroglu M. Substrate specificity of the Escherichia coli Fpg protein (formamidopyrimidine-DNA glycosy- lase): excision of purine lesions in DNA produced by ionizing radiation or photosensitization. Biochemistry 31:106-110 (1992).
13. Dizdaroglu M, Laval J, Boiteux S. Substrate specificity of the Escherichia coli endonuclease III: excision of thymine and cytosine-derived lesions in DNA produced by radiation-generated free radicals. Biochemistry 32:12105-12111 (1993).
14. Ravanat J-L, Berger M, Boiteux S, Laval J, Cadet J. Excision of 7,8-dihydro-8-oxoguanine from DNA by the Fpg protein. J Chim Phys 90:871-879 (1993).
15. Demple B, Harrison L. Repair of oxidative damage to DNA: enzymology and biology. Annu Rev Biochem 63:915-948 (1994).
16. Hatahet Z, Kow YW, Purmal AA, Cunningham RP, Wallace SS. New substrates for old enzymes. 5-Hydroxy-2′-deoxycytidine and 5-hydroxy-2′-deoxyuridine are substrates for Escherichia coli endonuclease III and formamidopyrimidine DNA-N-glycosylase, while 5-hydroxy-2′-deoxyuridine is a substrate for uracil DNA N-glycosylase. J Biol Chem 269:18814-18820 (1994).
17. Boiteux S. Properties and biological functions of the NTH and FPG proteins of Escherichia coli: two DNA glycosylases that repair oxidative damage in DNA. J Photochem Photobiol B: Biol 19:87-96 (1993).
18. de Oliveira R, van der Kemp PA, Thomas D, Geiger A, Nehls P, Boiteux S. Formamidopyrimidine DNA glycosylase in the yeast Saccharomyces cerevisiae. Nucleic Acids Res 22:3766-3764 (1994).
19. Hilbert TP, Boorstein RJ, Kung HC, Bolton PH, Xing D, Cunningham RP, Teebor GW. Purification of a mammalian homologue of Escherichia coli endonuclease III: identification of a bovine pyrimidine hydrate-thymine glycol-DNA glycosylase/AP lyase by irreversible cross linking to a thymine glycol-containing oligodeoxynucleotide. Biochemistry 35:2505-2511 (1996).
20. Tajiri T, Maki H, Sekiguchi M. Functional cooperation of MutT, MutM and MutY proteins in preventing mutations caused by spontaneous oxidation of guanine nucleotide in Escherichia coli. Mutat Res 336:257-267 (1995).
21. van der Kemp PA, Thomas D, Barbey R, de Oliveira R, Boiteux S. Cloning and expression in Escherichia coli of the OGG1 gene of Saccharomyces cerevisiae, which codes for a DNA glycosylase that excises 7,8-dihydro-8-oxoguanine and 2,6-diamino-4-hydroxy-5-N-methylformamidopyrimidine. Proc Natl Acad Sci USA 93:5197-5202 (1996).
22. Cadet J, Weinfeld M. Detecting DNA damage. Anal Chem 65:675A-682A (1993).
23. Floyd RA, Watson JJ, Wong PK, Altmiller DH, Rickard RC. Hydroxyl free radical adduct of deoxyguanosine: sensitive detection and mechanism of formation. Free Radic Res Commun 1:163-172 (1986).
24. Berger M, Anselmino C, Mouret J-F, Cadet J. High performance liquid chromatography-electrochemical assay for monitoring the formation of 8-oxo-7,8-dihydroadenine and its related 2′-deoxynucleoside. J Liq Chromatogr 13:929-932 (1990).
25. Wagner JR, Hu C-C, Ames BN. Endogenous oxidative damage of deoxycytidine in DNA. Proc Natl Acad Sci USA 89:3380-3384 (1992).
26. Dizdaroglu M. Chemical determination of free radical-induced damage to DNA. Free Radical Biol Med 10:225-242 (1991).
27. Dizdaroglu M. Formation of an 8-hydroxyguanine moiety in deoxyribonucleic acid on γ-irradiation in aqueous solution. Biochemistry 24:4476-4481 (1985).
28. Aruoma OI, Halliwell B, Dizdaroglu M. Iron ion-dependent modification of bases in DNA by the Superoxide radical-generating system hypoxanthine/xanthine oxidase. J Biol Chem 264:13024-13028 (1989).
29. Spencer JPE, Jenner A, Aruoma OI, Evans PJ, Kaur H, Dexter DT, Jenner P, Lees AJ, Marsden DC, Halliwell B. Intense oxidative DNA damage promoted by L-DOPA and its metabolites. Implication for neurodegenerative disease. FEBS Lett 353:246-250 (1994).
30. Fuciarelli AF, Sisk, EC, Thomas RM, Miller DL. Induction of base damage in DNA solutions by ultrasonic cavitation. Free Radic Biol Med 18:231-238 (1995).
31. Djuric Z, Heilbrun LK, Reading BA, Boomer A, Valeriote FA, Martino S. Effects of low-fat diet on levels of oxidative damage to DNA in human peripheral nucleated blood cells. J Natl Cancer Inst 83:766-769 (1991).
32. Malins DC, Haimanot R. Major alterations in the nucleotide structure of DNA in cancer of the female breast. Cancer Res 51:5430-5432 (1991).
33. Nackerdien Z, Olinski R, Dizdaroglu M. DNA base damage in chromatin of γ-irradiated cultured human cells. Free Radic Res Commun 16:259-273 (1992).
34. Mori T, Dizdaroglu M. Ionizing radiation causes greater DNA base damage in radiation-sensitive mutant M10 cells than in parent mouse lymphoma L5178Y cells. Radiat Res 140:85-90 (1994).
35. Jaruga P, Zastawny TH, Skokowski J, Dizdaroglu M, Olinski R. Oxidative DNA base damage and antioxidant enzyme activities in human lung cancer. FEBS Lett 341:59-64 (1994).
36. Wang Y-J, Ho Y-S, Lo M-J, Lin J-K. Oxidative modification of DNA bases in rat liver and lung during chemical carcinogenesis and aging. Chem-Biol Interact 94:135-145 (1995).
37. Höss M, Jaruga P, Zastawny TH, Dizdaroglu M, Pääbo S. DNA damage and DNA sequence retrieval from ancient tissues. Nucleic Acids Res 24:1304-1307 (1996).
38. Tchou J, Bodepudi V, Shibutani S, Antoshechkin I, Miller J, Grollman AP, Johnson F. Substrate specificity of Fpg protein. J Biol Chem 269:15318-15324 (1994).
39. Tchou J, Grollman AP. The catalytic mechanism of Fpg protein. Evidence for a Schiff base intermediate and amino terminus localization of the catalytic site. J Biol Chem 270:11671-11677 (1995).
40. Zastawny TH, Doetsch PW, Dizdaroglu M. A novel activity of E. coli uracil DNA N-glycosylase. Excision of isodialuric acid (5,6-dihydroxyuracil), a major product of oxidative DNA damage, from DNA. FEBS Lett 364:255-258 (1995).
41. Jaruga P, Dizdaroglu M. Repair of products of oxidative DNA base damage in human cells. Nucleic Acids Res 24:1389-1394 (1996).
42. Dizdaroglu M, Karakaya A, Jaruga P, Slupphaug G, Krokan HE. Novel activities of human uracil DNA TV-glycosylase for cytosine-derived products of oxidative DNA damage. Nucleic Acids Res 24:418-422 (1996).
43. Hulliwell B, Dizdaroglu M. The measurement of oxidative damage to DNA by HPLC and GC/MS techniques. Free Radic Res Commun 16:15-28 (1992).
44. Halliwell B. Oxidative DNA damage: meaning and measurement. In: DNA and Free Radicals (Halliwell B, Oruoma OI, eds). Chichester, England:Ellis Horwood, 1993;67-79.
45. Malins DC, Holmes EH, Polissar NL, Gunselman SJ. The etiology of breast cancer. Cancer 71:3036-3043 (1993).
46. Nagashima M, Tsuda H, Takenoshita S, Nagamachi Y, Hirohashi S, Yokota J, Kasai H. 8-Hydroxydeoxyguanosine levels in DNA of human breast cancers are not significantly different from those of non-cancerous breast tissues by HPLC-ECD method. Cancer Lett 90:157-162 (1995).
47. 32P-postlabeling. Anal Biochem 201:127-133 (1992).
48. Chernikov AV, Usacheva AM, Bruskov VI. Depurination of 8-oxo-7,8-dihydroguanine (8-hydroxyguanine) nucleosides. Biochemistry (Moscow) 61:35-38 (1996).
49. Douki T, Berger M, Raoul S, Ravanat J-L, Cadet J. Determination of 8-oxopurines in DNA by HPLC using amperometric detection. In: Analysis of Free Radicals in Biological Systems (Favier AE, Cadet J, Kalyanaraman B, Fontecave M, Pierre J-L, eds). Basel:Birkhaüser Verlag, 1995:213-224.
50. Teixeira AJR, Ferreira MR, Gommers-Ampt JH, van de Werken G, Westra JG, Stavenuiter JFC, de Jong APJM. Method for the analysis of oxidized nucleosides by gas chromatography/ mass spectrometry. Anal Biochem 214:474-483 (1993).
51. Teixeira AJR, Ferreira MR, van Dijk WJ, van de Werken G, Westra JG, de Jong APJM. Analysis of 8-hydroxy-2′-deoxyguanosine in rat urine and liver DNA by stable istope dilution gas chromatography/mass spectrometry. Anal Biochem 226:307-319 (1995).
52. Ravanat J-L, Turesky RJ, Gremaud E, Trudel LJ, Stadler RH. Determination of 8-oxoguanine in DNA by gas chromatography-mass spectrometry and HPLC-electrochemical detection: overestimation of the background level of the oxidized base by the gas chromatography-mass spectrometry assay. Chem Res Toxicol 8:1039-1045 (1995).
53. Ravanat J-L, Douki T, Turesky RJ, Cadet J. Measurement of oxidized bases in DNA. Comparison between HPLC-EC and GC-MS assays. J Chim Phys 94:306-312 (1997).
54. Hamberg M, Zhang L-Y. Quantitative determination of 8-hydroxyguanine and guanine by isotope dilution mass spectrometry. Anal Biochem 229:336-344 (1995).
55. Douki T, Delatour T, Bianchini F, Cadet J. Observation and prevention of an artefactual formation of oxidized DNA bases and nucleosides in the GC-EIMS method. Carcinogenesis 17:347-353 (1996).
56. Kelley JA, Abbasi MA, Beisler JA. Silylation mediated oxidation of dihydropyrimidine bases and nucleosides. Anal Biochem 103:203-213 (1980).
57. Malins DC, Polissar NL, Gunselman SJ. Progression of human breast cancers to the metastatic state is linked to hydroxyl radical-induced DNA damage. Proc Natl Acad Sci USA 93:2557-2563 (1996).
58. Djuric Z, Heilbrun LK, Simon MS, Smith D, Luongo DA, LoRusso PM, Martino S. Levels of 5-hydroxymethyl-2′-deoxyuridine in DNA from blood as a marker of breast cancer. Cancer 4:691-696 (1996).
59. Swarts SG, Smith GS, Miao L, Wheeler KT. Effects of formic acid hydrolysis on the quantitative analysis of radiation-induced DNA base damage products assayed by gas chromatography. Radiat Environ Biophys 35:41-53 (1996).
60. Douki T, Delatour T, Paganon F, Cadet J. Measurement of oxidative damage at pyrimidine bases in γ-irridiated DNA. Chem Res Toxicol 9:1145-1151 (1996).
61. Floyd RA, West MS, Eneff KL, Schneider JE, Wong PK, Tingey DT, Hogsett WE. Conditions influencing yield and analysis of 8-hydroxy-2′-deoxyguanosine in oxidatively damaged DNA. Anal Biochem 188:155-158 (1990).
62. Claycamp HG. Phenol sensitization of DNA to subsequent oxidative damage in 8-hydroxyguanine assays. Carcinogenesis 13:1289-1292 (1992).
63. Harris G, Bashir S, Winyard PG. 7,8-Dihydro-8-oxo-2′-deoxyguanosine present in DNA is not simply an artifact of isolation. Carcinogenesis 15:411-413 (1994).
64. Finnegan MTV, Herbert KE, Evans MD, Griffiths HR, Lunec J. Evidence for sensitisation of DNA to oxidative damage during oxidation. Free Radic Biol Med 20:93-98 (1996).
65. Adachi S, Zeisig M, Möller L. Improvements in the analytical method for 8-hydroxydeoxyguanosine in nuclear DNA. Carcinogenesis 16:253-258 (1995).
66. Nakae D, Mizumoto Y, Kobayashi E, Noguchi O, Konishi Y. Improved genomic/nuclear DNA extraction for 8-hydroxyguanosine analysis of small amounts of rat liver tissue. Cancer Lett 97:233-239 (1995).
67. Asami S, Hirano T, Yamaguchi R, Tomioka Y, Itoh H, Kasai H. Increase of a type of oxidative DNA damage, 8-hydroxyguanine, and its repair activity in human leukocytes by cigarette smoking. Cancer Res 56:2546-2549 (1996).
68. Nakajima M, Takeuchi T, Morimoto K. Determination of 8-hydroxydeoxyguanosine in human cells under oxygen-free conditions. Carcinogenesis 17:787-791 (1996).
69. Nakajima M, Takeuchi T, Takeshita T, Morimoto K. 8-Hydroxydeoxyguanosine in human leukocyte DNA and daily health practice factors: effects of individual alcohol sensitivity. Environ Health Perpsect 104:1336-1338 (1996).
70. Collins AR, Dušinská M, Gedik CM, Štětina R. Oxidative damage to DNA: do we have a reliable biomarker? Environ Health Perspect 104 (suppl 3):465-469 (1996).
71. Dušinská M, Collins A. Detection of oxidised purines and UV-induced photoproducts in DNA of single cells, by inclusion of lesion-specific enzymes in the comet assay. ATLA 24:405-411 (1996).
72. Epe B, Hegler J. Oxidative DNA damage: endonuclease fingerprint. Methods Enzymol 234:122-131 (1994).
73. Pflaum M, Boiteux S, Epe B. Visible light generates oxidative DNA base damage in high excess of strand breaks in mammalian cells. Carcinogenesis 15:297-300 (1994).
74. Epe B. DNA damage profiles induced by oxidizing agents. Rev Physiol Biochem Pharmacol 127:223-249 (1996).
75. 32P-postlabeling assay and the basal levels in rat tissues. Carcinogenesis 17:917-924 (1996).
76. Hariharan PV, Cerutti P. Formation and repair of γ-ray induced thymine damage in Micrococcus radiodurans. J Mol Biol 66:65-81 (1972).
77. Hariharan PV, Courtney J, Eleczko S. Production of hydroxyl radicals in cell systems exposed to haematoporphyrin and red light. Int J Radiat Biol 37:691-694 (1980).
78. Cadet J, Berger M. Radiation-induced decomposition of the purine bases within DNA and related model compounds. Int J Radiat Biol 47:127-143 (1985).
79. 32P-Postlabeling measurement of adenine N-1 oxide in cellular DNA exposed to hydrogen peroxide. Chem Res Toxicol 3:102-110 (1990).
80. Cadet J, Odin F, Mouret J-F, Polverelli M, Audic A, Giacomoni P, Favier A, Richard M-J. Chemical and biochemical postlabeling methods for singling out specific oxidative DNA lesions. Mutat Res 275:343-354 (1992).
81. Musarrat J, Wani AA. Quantitative immuno-analysis of promutagenic 8-hydroxy-2′-deoxyguanosine in oxidized DNA. Carcinogenesis 15:2037-2043 (1994).
82. Park EU, Shigenaga MK, Degan P, Korn TS, Kitzler JW, Wehr CM, Kolachana P, Ames BN. Assay of excised oxidative DNA lesions: isolation of 8-oxoguanine and its nucleoside derivatives from biological fluids with a monoclonal antibody column. Proc Natl Acad Sci USA 89:3375-3379 (1992).
83. Girault I, Shuker DEC, Cadet J, Molko D. Use of morpholinonucleosides to conjugate oxidized DNA bases to proteins. Bioconjugate Chem 4:445-450 (1996).