Methods of DNA adduct determination and their application to testing compounds for genotoxicity

Environmental and Molecular Mutagenesis

Volumn 35, Issue 3, 2000, Pages 222-233

  Phillips, D H ^a   Farmer, P B ^b   Beland, F A ^c   Nath, R G ^d   Poirier, M C ^e   Reddy, M V ^f   Turteltaub, K W ^g  

^a INSTITUTE OF CANCER RESEARCH   (United Kingdom)

^b UNIVERSITY OF LEICESTER   (United Kingdom)

^c NATIONAL CENTER FOR TOXICOLOGICAL RESEARCH   (United States)

^d UK   (United States)

^e NATIONAL CANCER INSTITUTE   (United States)

^f MERCK RESEARCH LABORATORIES   (United States)

^g LAWRENCE LIVERMORE NATIONAL LABORATORY   (United States)

Author keywords

32P postlabeling; DNA adducts; Endogenous DNA damage; Genotoxicity; Immunoassay; Mass spectrometry; Radioactivity

Indexed keywords

DNA; PHOSPHORUS 32;

CONFERENCE PAPER; DIAGNOSTIC TEST; DNA ADDUCT; DNA BINDING; DNA DETERMINATION; GENOTOXICITY; INTERNATIONAL COOPERATION; MASS SPECTROMETRY; PHYSICAL CHEMISTRY; QUANTITATIVE DIAGNOSIS;

DNA ADDUCTS; MASS SPECTROMETRY; MUTAGENICITY TESTS; PHOSPHORUS RADIOISOTOPES; SENSITIVITY AND SPECIFICITY;

EID: 0034070816     PISSN: 08936692     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1098-2280(2000)35:3<222::AID-EM9>3.0.CO;2-E     Document Type: Conference Paper

References (100)

1. Adams SP, Laws GM, Storer RD, Kraynak AR, DeLuca JG, Nichols WW. 1994. Co-purification of gastric mucoproteins with DNA: an explanation for the reported "interaction" of omeprazole with DNA in rat tissues. Mutat Res 322:307-320.
2. Ames BN, Gold LS, Willett WC. 1995. The causes and prevention of cancer. Proc Natl Acad Sci USA 92:5258-5265.
3. Arimoto-Kobayashi S, Kaji K, Sweetman GM, Hayatsu H. 1997. Mutation and formation of methyl- and hydroxylguanine adducts in DNA caused by N-nitrosodimethylamine and N-nitrosodiethylamine with UVA irradiation. Carcinogenesis 18:2429-2433.
4. 1 in human urine. Environ Health Perspect 62:105-108.
5. Beland FA, Kadlubar FF. 1990. Metabolic activation and DNA adducts of aromatic amines and nitroaromatic hydrocarbons. In: Cooper CS, Grover PL. editors. Chemical carcinogenesis and mutagenesis I. Heidelberg: Springer-Verlag. p 267-325.
6. Beland FA, Poirier MC. 1993. Significance of DNA adduct studies in animal models for cancer molecular dosimetry and risk assessment. Environ Health Perspect 99:5-10.
7. Bennett CL. 1979. Radiocarbon dating with accelerators. Am Scientist 67:450-457.
8. Beukens RP. 1992. Radiocarbon accelerator mass spectrometry: hackground, precision and accuracy. In: Taylor RE, Long A, Kra RS, editors. Radiocarbon after four decades. New York: Springer-Verlag. p 230-239.
9. Burcham PC. 1998. Genotoxic lipid peroxidation products: their DNA damaging properties and role in formation of endogenous DNA adducts. Mutagenesis 13:287-305.
10. 1. Carcinogenesis 11:2133-2135.
11. 32P-postlabelling of DNA adducts induced by a Fenton-type oxygen radical-generating system. Carcinogenesis 13:1127-1135.
12. Chaudhary AK, Nokubo M, Oglesby TD, Marnett LJ, Blair IA. 1995. Characterisation of endogenous DNA adducts by liquid chromatography/electrospray ionization tandem mass spectrometry. J Mass Spectrum 30:1157-1166.
13. Chaudhary AK, Nokubo M, Reddy GR, Yeola SN, Morrow JD, Blair IA, Marnett LJ. 1994. Detection of endogenous malondialdehyde-deoxyguanosine adducts in human liver. Science 265:1580-1582.
14. Chen M, Lu X, Chen G, Xu S, Shen L, Li D, Zhang Y, Gong P, Zhang Y, Zhou W. 1997. Status of the SINR mini-cyclotron AMS facility. Nucl Instrum Methods Phys Res B: 102-106.
15. Chung FL, Chen HJ, Nath RG. 1996. Lipid peroxidation as a potential endogenous source for the formation of exocyclic DNA adducts. Carcinogenesis 17:2105-2111.
16. 2-propanode-oxyguanosine adducts. Mutat Res 424:71-81.
17. Creek MR, Frantz CE, Fultz E, Haack K, Redwine K, Shen N, Turteltaub KW, Vogel JS. 1994. C-14 Ams quantification of biomolecular interactions using microbore and plate separations. Nucl Instrum Meth Phys Res B 92:454-458.
18. 14C]-benzene in B6C3F1 mice. Carcinogenesis 18:2421-2427.
19. Dahl GA, Miller JA, Miller EC. 1978. Vinyl carbamate as a promutagen and a more carcinogenic analog of ethyl carbamate. Cancer Res 38:3793-3804.
20. 32P-postlabeling. Cancer Res 59:4829-4833.
21. Dizdaroglu M. 1993. Quantitative determination of oxidative hase damage in DNA by stable isotope-dilution mass spectrometry. FEBS Lett 315:1-6.
22. Djuric Z, Heilbrun LK, Reading BA, Boomer A, Valeriote FA, Martino S. 1991. Effects of a low-fat diet on levels of oxidative damage to DNA to human peripheral nucleated blood cells. J Natl Cancer Inst 83:766-769.
23. Duggan JL. 1994. Ion beam accelerators for research and industry (1995): an organizer's perspective. Proceedings of the 13th International Conference on the Application of Accelerators in Research and Industry, Denton, Texas.
24. Elmore DE. 1987. Ultrasensitive radioisotope, stable-isotope, and trace-element analysis in the biological sciences using tandem accelerator mass spectrometry. Biol Trace Element Res 12:231-245.
25. Farooq S, Bailey E, Farmer PB, Jukes R, Lamb JH, Hernandez H, Sram R, Topinka J. 1997. Determination of cis-thymine glycol in DNA by gas chromatography-mass spectrometry with selected ion recording and multiple reaction monitoring. J Chromatogr B Biomed Sci Appl 702:49-60.
26. Foiles PG, Akerkar SA, Carmella SG, Kagan M, Stoner GD, Resau JH, Hecht SS. 1991. Mass spectrometric analysis of tobacco-specific nitrosamine-DNA adducts in smokers and nonsmokers. Chem Res Toxicol 4:364-368.
27. Frantz CE, Bangerter C, Fultz E, Mayer KM, Vogel JS, Turteltaub KW. 1995. Dose-response studies of MeIQx in rat liver and liver DNA at low doses. Carcinogenesis 16:367-373.
28. 41Ca AMS measurement at LLNL. Nucl Instrum Methods Phys Res B 557-561.
29. 32P-postlabeling. Chem Res Toxicol 7:733-739.
30. 32P-postlabelling assay after either 1-butanol extraction or nuclease P1 treatment. Cancer Lett 45:7-12.
31. Gaylor DW, Kadlubar FF, Beland FA. 1992. Application of biomarkers to risk assessment. Environ Health Perspect 98:139-141.
32. 32P-postlabeling. Environ Mol Mutagenesis 32:344-350.
33. Gove HE. 1992. The history of AMS, its advantages over decay counting: applications and prospects. In: Taylor RE, Long A, Kra RS, editors. Radiocarbon after four decades. New York: Springer-Verlag. p 214-229.
34. 32P-postlabeling analysis of aromatic carcinogen:DNA adducts. Cancer Res 45:5656-5662.
35. 32P-adduct assay: comparative recoveries of structurally diverse DNA adducts in the various enhancement procedures. Carcinogenesis 9:1687-1693.
36. Gupta RC, Lutz WK. 1999. Background DNA damage for endogenous and unavoidable exogenous carcinogens: a basis for spontaneous cancer incidence? Mutat Res 424:1-8.
37. Halliwell B, Dizdaroglu M. 1992. The measurement of oxidative damage to DNA by HPLC and GC/MS techniques. Free Radic Res Commun 16:75-87.
38. Han X, Liehr JG. 1992. Induction of covalent DNA adducts in rodents by tamoxifen. Cancer Res 52:1360-1363.
39. 32P-postlabelling method. In: Phillips DH, Castegnaro M, Bartsch H, editors. Postlabelling methods for detection of DNA damage. Lyon: IARC. p 51-63.
40. Izzotti A. 1998. Detection of modified DNA nucleotides by postlabelling procedures. Toxicol Methods 8:175-205.
41. Kautiainen A, Vogel JS, Turteltaub KW. 1997. Dose-dependent binding of trichloroethylene to hepatic DNA and protein at low doses in mice. Chem-Biol Interact 106:109-121.
42. 32P-postlabelling method for the detection of 7-alkylguanine adducts formed by the reaction of different 1,2-alkyl epoxides with DNA. Carcinogenesis 16:483-489.
43. 32P-postlabelling studies in hormonal carcinogenesis. In: Phillips DH, Castegnaro M, Bartsch H, editors. Postlabelling methods for detection of DNA damage. Lyon: IARC. p 149-155.
44. Lin D, Lay JO, Jr., Bryant MS, Malaveille C, Friesen M, Bartsch H, Lang NP, Kadlubar FF. 1994. Analysis of 4-aminobiphenyl-DNA adducts in human urinary bladder and lung by alkaline hydrolysis and negative ion gas chromatography-mass spectrometry. Environ Health Perspect 102(Suppl 6):11-16.
45. Liu Z, Young-Sciame R, Hecht SS. 1996. Liquid chromatography-electrospray ionization mass spectrometric detection of an ethenodeoxyguanosine adduct and its hemiaminal precursors in DNA reacted with α-acetoxy-N-nitrosopiperidine and cis-4-oxo-2-pentenal. Chem Res Toxicol 9:774-780.
46. Lutz WK. 1979. In vivo covalent binding of organic chemicals to DNA as a quantitative indicator in the process of chemical carcinogenesis. Mutat Res 65:289-356.
47. Lutz WK. 1982. The covalent binding index - DNA binding in vivo as a quantitative indicator for genotoxicity. In: Banbury Report 13. Bridges BA, Butterworth BE, Weinstein IB, editors. Indicators of genotoxic exposure. Cold Spring Harbor: Cold Spring Harbor Laboratory. p 189-204.
48. Lutz WK. 1986. Quantitative evaluation of DNA binding data for risk estimation and for classification of direct and indirect carcinogens. J Cancer Res Clin Oncol 112:85-91.
49. Marnett LJ. 1999. Lipid peroxidation-DNA damage by malondialdehyde. Mutat Res 424:83-95.
50. Martin CN, Lawley PD, Phillips DH, Venitt S, Waters R. 1993. Measurement of covalent binding to DNA in vivo. In: Kirkland DJ, Fox M, editors. Supplementary mutagenicity tests: UKEMS recommended procedures. Cambridge: Cambridge University Press. p 78-104.
51. 32P-postlabelling assay. Carcinogenesis 10:1557-1559.
52. 32P-Postlabeling of N-(deoxyguanosin-8-yl)arylamine adducts. A comparative study of labeling efficiencies. Chem Res Toxicol 12:661-669.
53. 14C isotope ratio mass spectrometer for biomedical applications. Proceeding of the 7th International Conference on AMS. Nucl Instrum Meth Phys Res B 1052-1056.
54. Nair J, Barbin A, Velic I, Bartsch H. 1999. Etheno DNA-base adducts from endogenous reactive species. Mutat Res 424:59-69.
55. 2-propanodeoxyguanosine adducts as common DNA lesions in rodents and humans. Proc Natl Acad Sci U S A 91:7491-7495.
56. 2-propanodeoxyguanosine adducts as potential endogenous DNA lesions in rodent and human tissues. Cancer Res 56:452-456.
57. Nath RG, Ocando JE, Richie JP, Chung FL. 1997. Effect of glutathione depletion on exocyclic adduct levels in the liver DNA of F344 rats. Chem Res Toxicol 10:1250-1253.
58. Nath RG, Randerath K, Li D, Chung FL. 1996b. Endogenous production of DNA adducts. Regul Toxicol Pharmacol 23:22-28.
59. Nestmann ER, Bryant DW, Carr CJ, Fennell TT, Gallagher JE, Gorelick NJ, Swenberg JA, Williams GM. 1996. Toxicological significance of DNA adducts: summary of discussions with an expert panel. Regul Toxicol Pharmacol 24:9-18.
60. Otteneder M, Lutz WK. 1999. Correlation of DNA adduct levels with tumor incidence: carcinogenic potency of DNA adducts. Mutat Res 424:237-247.
61. 32P-postlabelling assay. Mutat Res 378:1-12.
62. Phillips DH, Castegnaro M., on behalf of trial participants. 1999. Standardization and validation of DNA adduct postlabelling methods: report of interlaboratory trials and production of recommended protocols. Mutagenesis 14:301-315.
63. Phillips DH, Hewer A, Osborne MR. 1992. Interaction of omeprazole with DNA in rat tissues. Mutagenesis 7:277-283.
64. Poirier MC. 1991. Development of immunoassays for the detection of carcinogen-DNA adducts. In: Groopman JD, Skipper PL, editors. Molecular dosimetry and human cancer. Boca Raton: CRC Press. p 211-229.
65. Poirier MC. 1993. Antisera specific for carcinogen-DNA adducts and carcinogen-modified DNA: applications for detection of xenobiotics in biological samples. Mutat Res 288:31-38.
66. Poirier MC, Beland FA. 1992. DNA adduct measurements and tumor incidence during chronic carcinogen exposure in animal models: implications for DNA adduct-based human cancer risk assessment. Chem Res Toxicol 5:749-755.
67. Poirier MC, Weston A. 1991. DNA adduct determination in humans. In: Gledhill B, Mauro F, editors. New horizons in biological dosimetry. New York: Wiley-Liss Inc. p 205-218.
68. Polach HA. 1984. Radiocarbon targets for AMS: a review of perceptions, aims and achievemants. Nucl Instrum Meth Phys Res B 233:259-264.
69. Qian GS, Ross RK, Yu MC, Yuan JM, Gao YT, Henderson BE, Wogan GN, Groopman JD. 1994. A follow-up study of urinary markers of aflatoxin exposure and liver cancer risk in Shanghai, People's Republic of China. Cancer Epidemiol Biomarkers Prev 3:3-10.
70. Ranasinghe A, Scheller N, Wu KY, Upton PB, Swenberg JA. 1998. Application of gas chromatography/electron capture negative chemical ionization high-resolution mass spectrometry for analysis of DNA and protein adducts. Chem Res Toxicol 11:520-526.
71. Randerath K, Li D, Moorthy B, Randerath E. 1993. 1-compounds: endogenous DNA markers of nutritional status, ageing, tumour promotion and carcinogenesis. In: Phillips DH, Castegnaro M, Bartsch H, editors. Postlabelling methods for detection of DNA damage. Lyon: IARC. p 157-165.
72. 32P-Postlabelling methods for DNA adduct detection: overview and critical evaluation. Drug Metab Rev 26:67-85.
73. 32P-postlabeling assay based on the specific enzymatic conversion of bulky DNA lesions to radiolabeled dinucleotides and nucleoside 5′-monophosphates. Carcinogenesis 10:1231-1239.
74. Randerath K, Randerath E, Zhou GD, Li D. 1999. Bulky endogenous DNA modifications (I-compounds): possible structural origins and functional implications. Mutation Res 424:183-194.
75. 32P-Labeling test for DNA damage. Proc Natl Acad Sci U S A 78:6126-6129.
76. Ravanat JL, Duretz B, Guiller A, Douki T, 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 Biomed Sci Appl 715:349-356.
77. Ravanat JL, Turesky RJ, Gremaud E, Trudel LJ, Stadler RH. 1995. 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.
78. 32P-Postlabeling detection of thymine glycols: evaluation of adduct recoveries alter enhancement with affinity chromatography, nuclease P1, nuclease S1, and polynucleotide kinase. Cancer Commun 3:109-117.
79. 32P-postlabeling of adducts as labeled nucleoside bisphosphates, dinucleotides and nucleoside monophosphates. Carcinogenesis 11:1349-1357.
80. 32P-Postlabeling test for covalent DNA binding of chemicals in vivo: application to a variety of aromatic carcinogens and methylating agents. Carcinogenesis 5:231-243.
81. 32P-postlabeling test for structurally diverse DNA adducts. Carcinogenesis 7:1543-1551.
82. 14C]ethyl carbamate (urethan). Carcinogenesis 3:539-546.
83. Rouzer CA, Chaudhary AK, Nokuho M, Ferguson DM, Reddy GR, Blair IA, Marnett LJ. 1997. Analysis of the matondialdehyde-2′-deoxyguanosine adduct pyrimidopurinone in human leukocyte DNA by gas chromatography/electron capture/negative chemical ionization/mass spectrometry. Chem Res Toxicol 10:181-188.
84. 32 P-postlabelling to investigate DNA adduct formation by bile acids in vitro: lack of evidence for covalent binding. Carcinogenesis 16:1489-1491.
85. Schutze D, Sagelsdorff P, Sepai O, Sabbioni G. 1996. Synthesis and quantification of DNA adducts of 4,4′-methylenedianiline. Chem Res Toxicol 9:1103-1112.
86. Shuker DEG, Farmer PB, 1992. Relevance of urinary DNA adducts as markers of carcinogen exposure. Chem Res Toxicol 5:450-460.
87. 32P-postlabelling: a sensitive technique for the detection of DNA adducts. Chemicke listy 92:661-668.
88. Sweetman GMA, Shuker DEG, Glover RP, Farmer PB. 1998. Mass spectrometry in carcinogenesis research. Adv Mass Spectrom 14:343-376.
89. Tretyakova N, Chiang SY, Walker VE, Swenberg JA. 1998. Quantitative analysis of 1,3-butadiene-induced DNA adducts in vivo and in vitro using liquid chromatography electrospray ionization tandem mass spectrometry. J Mass Spectrom 33:363-376.
90. Tretyakova N, Sangaiah R, Yen TY, Swenberg JA. 1997. Synthesis, characterization, and in vitro quantitation of N-7-guanine adducts of diepoxybutane. Chem Res Toxicol 10:779-785.
91. 32P-postlabeling. Princess Takamatsu Symp 23:93-102.
92. Turteltaub KW, Vogel JS, Frantz, CE, Shen N. 1992. Fate and distribution of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine in mice at a human dietary equivalent dose. Cancer Res 52:4682-4687.
93. Vogel JS, Turteltaub KW. 1992. Biomolecular tracing through accelerator mass spectrometry. Trends Anal Chem 11:142-149.
94. Vogel JS, Turteltaub KW, Felton JS, Gledhill BL, Nelson DE, Southon JR, Proctor ID, Davis JC. 1990. Application of AMS to the biomedical sciences. Nucl Instrum Meth Phys Res B 52:524-530.
95. Vogel JS, Turteltaub KW, Finkel R, Nelson DE. 1995. Accelerator mass spectrometry. Anal Chem 67:353A-359A.
96. 32P-Postlabelling of bile components: bulky adduct-like behaviour in polyethyleneimine-cellulose thin layer chromatography. Carcinogenesis 15: 2061-2064.
97. Weston A, Poirier MC. 1994. Development of methods for chemical carcinogen-DNA adduct determination in human tissues. In: Milman HA, Weisburger EK, editors. Handbook of carcinogen testing. 2nd ed. Park Ridge, NJ: Noyes Publications. p 672-700.
98. Weston A, Rowe ML, Manchester DK, Farmer PB, Mann DL, Harris CC. 1989. Fluorescence and mass spectral evidence for the formation of benzo[a]pyrene anti-diol-epoxide-DNA and -hemoglobin adducts in humans. Carcinogenesis 10:251-257.
99. While INH, de Matteis F, Davies A, Smith LL, Crofton-Sleigh C, Venitt S, Hewer A, Phillips DH. 1992. Genotoxic potential of tamoxifen and analogues in female Fischer F344/n rats, DBA/2 and C57B1/6 mice and in human MCL-5 cells. Carcinogenesis 13:2197-2203.
100. 2,3-ethenoguanine using liquid chromatography/electrospray ionization mass spectrometry. J Mass Spectrom 31:1271-1276.