Immunochemical, 32P-postlabeling, and GC/MS detection of 4-aminobiphenyl-DNA adducts in human peripheral lung in relation to metabolic activation pathways involving pulmonary N-oxidation, conjugation, and peroxidation

Mutation Research - Fundamental and Molecular Mechanisms of Mutagenesis

Volumn 378, Issue 1-2, 1997, Pages 97-112

  Culp, S J ^a   Roberts, D W ^a   Talaska, G ^a,c   Lang, N P ^b   Fu, P P ^a   Lay Jr , J O ^a   Teitel, C H ^a   Snawder, J E ^a,d   Von Tungeln, L S ^a   Kadlubar, F F ^a  

^a NATIONAL CENTER FOR TOXICOLOGICAL RESEARCH   (United States)

^b Special Treatment Section   (United States)

^c UNIVERSITY OF CINCINNATI   (United States)

^d NATIONAL INSTITUTE FOR OCCUPATIONAL SAFETY AND HEALTH   (United States)

Author keywords

4 Aminobiphenyl; 4 Nitrobiphenyl; Arylamine carcinogenesis; Myeloperoxidase; Peroxidative activation

Indexed keywords

2 FLUORENYLAMINE; 2 NAPHTHYLAMINE; 4 AMINOBENZOIC ACID; 4 BIPHENYLAMINE; 4,4' METHYLENEBIS(2 CHLOROANILINE); ACYLTRANSFERASE; BENZIDINE; CIGARETTE SMOKE; CYTOCHROME P450 ISOENZYME; HYDROGEN PEROXIDE; ICOSATETRAYNOIC ACID; INDOMETACIN; ISOENZYME; LIPOXYGENASE; MYELOPEROXIDASE; PHOSPHORUS 32; PROSTAGLANDIN SYNTHASE; SODIUM AZIDE; SULFADIMIDINE; 4 NITROBIPHENYL; 4-BIPHENYLAMINE; 4-NITROBIPHENYL; AMINOBIPHENYL DERIVATIVE; BENZIDINE DERIVATIVE; BENZO[A]PYRENE; BIPHENYL DERIVATIVE; CARCINOGEN; DRUG DERIVATIVE; GUANOSINE; N (8 GUANOSINYL) 4 BIPHENYLAMINE; N-(GUANOSIN-8-YL)-4-AMINOBIPHENYL; PEROXIDASE; PHOSPHORUS; SULFOTRANSFERASE;

ARTICLE; ASSAY; CONJUGATION; CONTROLLED STUDY; CYTOSOL; DNA ADDUCT; ENVIRONMENTAL EXPOSURE; GAS CHROMATOGRAPHY; HUMAN; HUMAN TISSUE; IMMUNOCHEMISTRY; INTERMETHOD COMPARISON; ISOTOPE LABELING; LUNG; MASS SPECTROMETRY; METABOLIC ACTIVATION; MICROSOME; NEUTROPHIL; OXIDATION; PEROXIDATION; PRIORITY JOURNAL; REACTION ANALYSIS; REDUCTION; SMOKING; UROTHELIUM; BIOTRANSFORMATION; CHEMISTRY; ENZYME LINKED IMMUNOSORBENT ASSAY; ENZYMOLOGY; IMMUNOLOGY; LIVER; MASS FRAGMENTOGRAPHY; METABOLISM; OXIDATION REDUCTION REACTION;

ACYLTRANSFERASES; AMINOBIPHENYL COMPOUNDS; BENZIDINES; BENZO(A)PYRENE; BIOTRANSFORMATION; BIPHENYL COMPOUNDS; CARCINOGENS; CYTOSOL; DNA ADDUCTS; ENZYME-LINKED IMMUNOSORBENT ASSAY; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; GUANOSINE; HUMANS; LIVER; LUNG; MICROSOMES; OXIDATION-REDUCTION; PEROXIDASE; PEROXIDASES; PHOSPHORUS RADIOISOTOPES; SMOKING; SULFOTRANSFERASES;

EID: 0030814067     PISSN: 00275107     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0027-5107(97)00101-2     Document Type: Article

References (69)

1. IARC, Monographs on the Evaluation of Carcinogenic Risks to Humans, Overall Evaluation of Carcinogenesis: An Updating of International Agency for Research on Cancer, Monographs 1-42, Suppl. 7, 1987.
2. C. Patrianakos, D. Hoffmann, Chemical studies on tobacco smoke LXIV. On the analysis of aromatic amines in cigarette smoke, J. Anal. Toxicol. 3 (1979) 150-154.
3. F.F. Kadlubar, K.L. Dooley, C.H. Teitel, D.W. Roberts, R.W. Benson, M.A. Butler, J.R. Bailey, J.F. Young, P.W. Skipper, S.R. Tannenbaum, The frequency of urination and its effects on metabolism pharmacokinetics, blood hemoglobin adduct formation, and liver and urinary bladder DNA adduct levels in Beagle dogs administered the carcinogen, 4-aminobiphenyl, Cancer Res. 51 (1991) 4371-4377.
4. G. Talaska, A.Z.S.S. Al-Juburi, F.F. Kadlubar, Smoking related carcinogen-DNA adducts in biopsy samples of human urinary bladder: identification of N-(deoxyguanosin-8-yl)-4-aminobiphenyl as a major adduct, Proc. Natl. Acad. Sci. USA 88 (1991) 5350-5354.
5. G. Curigliano, Y.-J. Zhang, L.-Y. Wang, G. Flamini, A. Alcini, C. Ratto, M. Giustacchini, E. Alcini, A. Cittadini, R.M. Santella, Immunohistochemical quantitation of 4-aminobiphenyl-DNA adducts and p53 nuclear overexpression in T1 bladder cancer of smokers and nonsmokers, Carcinogenesis 17 (1996) 911-916.
6. M.S. Bryant, P.L. Skipper, S.R. Tannenbaum, M. Maclure, Hemoglobin adducts of 4-aminobiphenyl in smokers and nonsmokers, Cancer Res. 47 (1987) 602-608.
7. M.A. Butler, F.P. Guengerich, F.F. Kadlubar, Metabolic oxidation of the carcinogens 4-aminobiphenyl and 4,4′-methylenebis(2-chloroaniline) by human hepatic microsomes and by purified rat hepatic cytochrome P-450 monooxygenases, Cancer Res. 49 (1989) 25-31.
8. A.F. Badawi, A. Hirvonen, D.A. Bell, F.F. Kadlubar, Role of aromatic amine acetyltransferases, NAT1 and NAT2, in carcinogen-DNA adduct formation in the human urinary bladder, Cancer Res. 55 (1995) 5230-5237.
9. T.J. Flammang, Y. Yamazoe, R.W. Benson, D.W. Roberts, D.W. Potter, D.Z.J. Chu, N.P. Lang, F.F. Kadlubar, Arachidonic acid-dependent peroxidative activation of carcinogenic arylamines by extrahepatic human tissue microsomes, Cancer Res. 49 (1989) 1977-1982.
10. F.A. Beland, F.F. Kadlubar, Metabolic activation and DNA adducts of aromatic amines and nitroaromatic hydrocarbons, in: C.W. Cooper, P.L. Grover (Eds.), Handbook of Experimental Pharmacology vol. 94/1, Springer-Verlag, Germany, 1990, pp. 267-325.
11. IARC, Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Humans, Vol. 38, Tobacco Smoking, International Agency for Research on Cancer, Lyon, 1986.
12. J. Baron, J.M. Voight, Localization, distribution, and induction of xenobiotic-metabolizing enzymes and aryl hydrocarbon hydroxylase activity within lung, Pharmacol. Ther. 47 (1990) 419-445.
13. F.P. Guengerich, Purification and characterization of xenobiotic-metabolizing enzymes from lung tissue, Pharmacol. Ther. 45 (1990) 299-307.
14. T.J. Smith, G.D. Stoner, C.S. Yang, Activation of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) in human lung microsomes by cytochromes P450, lipoxygenase, and hydroperoxides, Cancer Res. 55 (1995) 5566-5573.
15. T. Shimada, H. Yamazaki, M. Mimura, Y.-F. Ueng, F.P. Guengerich, Y. Inui, Characterization of microsomal P450 enzymes involved in the oxidation of xenobiotic chemicals in human fetal livers and adult lungs, Drug Metab. Disp. 24 (1996) 515-522.
16. D.H. Phillips, A. Hewer, C.N. Martin, R.C. Garner, M.M. King, Correlation of DNA adduct levels in human lung with cigarette smoking, Nature 336 (1988) 790-792.
17. H. Bartsch, S. Petruzzelli, S. De Flora, E. Hietanen, A.-M. Camus, M. Castegnaro, O. Geneste, A. Camoirano, R. Saracci, C. Giuntini, Carcinogen metabolism and DNA adducts in human lung tissues as affected by tobacco smoking or metabolic phenotype: a case-control study on lung cancer patients, Mutation Res. 250 (1991) 103-114.
18. D. Ryberg, A. Hewer, D.H. Phillips, A. Haugen, Different susceptibility to smoking-induced DNA damage among male and female lung cancer patients, Cancer Res. 54 (1994) 5801-5803.
19. D.H. Phillips, B. Schoket, A. Hewer, E. Bailey, S. Kostic, I. Vincze, Influence of cigarette smoking on the levels of DNA adducts in human bronchial epithelium and white blood cells, Int. J. Cancer 46 (1990) 569-575.
20. R.K. Kaderlik, D.-X. Lin, N.P. Lang, F.F. Kadlubar, Advantages and limitations of laboratory methods for measurement of carcinogen-DNA adducts for epidemiological studies, Toxicol. Lett. 64/65 (1992) 469-475.
21. 32P-postlabelling or ELISA, Mutation Res. 292 (1993) 113-122.
22. J.K. Wiencke, K.T. Kelsey, A. Varkonyi, K. Semey, J.C. Wain, E. Mark, D.C. Christiani, Correlation of DNA adducts in blood mononuclear cells with tobacco carcinogen-induced damage in human lung, Cancer Res. 55 (1995) 4910-4914.
23. S. Kato, E.D. Bowman, A.M. Harrington, B. Blomeke, P.G. Shields, Human lung carcinogen-DNA adduct levels mediated by genetic polymorphisms in vivo, J. Natl. Cancer Inst. 87 (1995) 902-907.
24. D.W. Roberts, R.W. Benson, J.D. Groopman, T.J. Flammang, W.A. Nagel, A.J. Moss, F.F. Kadlubar, Immunochemical quantitation of DNA adducts derived from the human bladder carcinogen 4-aminobiphenyl, Cancer Res. 48 (1988) 6336-6342.
25. F.F. Kadlubar, G. Talaska, N.P. Lang, R.W. Benson, D.W. Roberts, Assessment of exposure and susceptibility to aromatic amine carcinogens, in: Methods for Detecting DNA Damaging Agents in Humans: Application in Cancer Epidemiology and Prevention, IARC Symposium No. 89, 1988, pp. 166-174.
26. V.L. Wilson, A. Weston, D.K. Manchester, G.E. Trivers, D.W. Roberts, F.F. Kadlubar, C.P. Wild, R. Montesano, J.C. Willey, D.L. Mann, C.C. Harris, Alkyl and aryl carcinogen adducts detected in human peripheral lung, Carcinogenesis 10 (1989) 2149-2153.
27. R. Willstätter, H. Kubli, Über die reduktion von nitroverbindungen nach der methode von Zinin, Chem. Ber. 41 (1908) 1936-1940.
28. C.G. Crawford, G.W.H.M. van Alphen, H.W. Cook, W.E.M. Lands, The effect of precursors, products, and product analogs of prostaglandin cyclooxygenase upon iris sphincter muscle, Life Sci. 23 (1978) 1255-1262.
29. F.P. Guengerich, Microsomal enzymes involved in toxicology - analysis and separation, in: A.W. Hayes (Ed.), Principles and Methods of Toxicology, Raven Press, New York, 1982, pp. 609-634.
30. E. Layne, Spectrophotometric and turbidimetric methods for measuring proteins, Methods Enzymol. 3 (1957) 447-454.
31. F.A. Beland, N.F. Fullerton, R.H. Heflich, Rapid isolation, hydrolysis and chromatography of formaldehyde-modified DNA, J. Chromatogr. 308 (1984) 121-131.
32. H. Seto, T. Ohkubo, T. Kanoh, M. Koike, K. Nakamura, Y. Kawahara, Determination of polycyclic aromatic hydrocarbons in the lung, Arch. Environ. Contam. Toxicol. 24 (1993) 498-503.
33. D.X. Lin, J.O. Lay Jr., M.S. Bryant, C. Malaveille, M. Friesen, H. Bartsch, N.P. Lang, F.F. Kadlubar, 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) (1994) 11-16.
34. PA (P-450IA2), the phenacetin O-deethylase, is primarily responsible for the hepatic 3-demethylation of caffeine and N-oxidation of carcinogenic arylamines, Proc. Natl. Acad. Sci. USA 86 (1989) 7696-7700.
35. R.J. Turesky, N.P. Lang, M.A. Butler, C.H. Teitel, F.F. Kadlubar, Metabolic activation of carcinogenic heterocyclic aromatic amines by human liver and colon, Carcinogenesis 12 (1991) 1839-1845.
36. H.-C. Chou, N.P. Lang, F.F. Kadlubar, Metabolic activation of the N-hydroxy derivative of the carcinogen 4-aminobiphenyl by human tissue sulfotransferases, Carcinogenesis 16 (1995) 413-417.
37. R.F. Minchin, P.T. Reeves, C.H. Teitel, M.E. McManus, B. Mojarrabi, K.F. Ilett, F.F. Kadlubar, N- and O-acetylation of aromatic and heterocyclic amine carcinogens by human monomorphic and polymorphic acetyltransferases expressed in Cos-1 cells, Biochem. Biophys. Res. Commun. 185 (1992) 839-844.
38. Y. Yamazoe, T.V. Zenser, D.W. Miller, F.F. Kadlubar, Mechanism of formation and structural characterization of DNA adducts derived from peroxidative activation of benzidine, Carcinogenesis 9 (1988) 1935-1941.
39. M.M. Bradford, A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding, Anal. Biochem. 72 (1976) 248-254.
40. K.L. Taylor, G.S. Guzman, C.A. Burgess, J.M. Kinkade Jr., Assembly of dimeric myeloperoxidase during posttranslational maturation in human leukemic HL-60 cells, Biochemistry 29 (1990) 1533-1539.
41. E.S. Bos, A.A. van der Doelen, N. van Rooy, A.H. Schuurs, 3,3′,5,5′-Tetramethylbenzidine as an Ames test negative chromogen for horseradish peroxidase in enzyme-immunoassay, J. Immunoassay 2 (1981) 187-204.
42. 32P-Postlabelling and mass spectrometric methods for analysis of bulky, polyaromatic carcinogen-DNA adducts in humans, J. Chromatogr. 580 (1992) 293-323.
43. 32P-Postlabelling analysis of bulky aromatic adducts, in: D.H. Phillips, M. Castegnaro, H. Bartsch (Eds.), Postlabelling Methods for Detection of DNA Adducts, IARC, Lyon, 1993, pp. 11-23.
44. F.F. Kadlubar, G.J. Hammons, The role of cytochrome P-450 in the metabolism of chemical carcinogens, in: F.P. Guengerich (Ed.), Mammalian Cytochromes P-450, Vol. 2, CRC, Boca Raton, FL, 1987, pp. 81-130.
45. F.A. Beland, D.T. Beranek, K.L. Dooley, R.H. Heflich, F.F. Kadlubar, Arylamine-DNA adducts in vitro and in vivo: their role in bacterial mutagenesis and urinary bladder carcinogenesis, Environ. Health Perspect. 49 (1983) 125-134.
46. Y. Tsuruta, V.V. Subrahmanyam, W. Marshall, P.J. O'Brien, Peroxidase-mediated irreversible binding of arylamine carcinogens to DNA in intact polymorphonuclear leukocytes activated by a tumor promoter, Chem. Biol. Interact. 53 (1985) 25-35.
47. Y. Yamazoe, R.W. Roth, F.F. Kadlubar, Reactivity of benzidine diimine with DNA to form N-(deoxyguanosine-8-yl)-benzidine, Carcinogenesis 7 (1986) 179-182.
48. R.S. Krauss, J. Angermann-Stewart, K.L. Dooley, F.F. Kadlubar, T.E. Eling, The formation of 2-aminofluorene-DNA adduct in vivo: evidence for peroxidase-mediated activation, J. Biochem. Toxicol. 4 (1989) 111-117.
49. M.F. Hughes, B.J. Smith, T.E. Eling, The oxidation of 4-aminobiphenyl by horseradish peroxidase, Chem. Res. Toxicol. 5 (1992) 340-345.
50. F.F. Kadlubar, M.A. Butler, B.E. Hayes, F.A. Beland, F.P. Guengerich, Role of microsomal cytochromes P-450 and prostaglandin H-synthase in 4-aminobiphenyl-DNA adduct formation, in: J.O. Miners, D.J. Birkett, R. Drew, B.K. May, M.E. McManus (Eds.), Microsomes and Drug Oxidations, Proceeding of the 7th International Symposium, Adelaide, Australia, Taylor and Francis Ltd. Great Britain, 1987, pp. 370-379.
51. M. Yamada, M. Mori, T. Sugimura, Myeloperoxidase-catalyzed binding of 3-amino-l-methyl-5H-pyrido[4,3-b]idole, a tryptophan pyrolysis product to protein, Chem. Biol. Interact. 33 (1980) 19-33.
52. M.A. Trush, T.A. Kensler, An overview of the relationship between oxidative stress and chemical carcinogenesis, Free Radical Biol. Med. 10 (1991) 201-209.
53. J.L. Mauderly, Y.S. Chang, M.B. Snipes, Particle overload in toxicological studies: friend or foe?, J. Aerosol Med. 3 (1990) S169-S187.
54. C.K. Chow, Cigarette smoking and oxidative damage in the lung, Ann. N.Y. Acad. Sci., 1993, 289-298.
55. E.A. Rosvold, K.A. McGlynn, E.D. Lustbader, K.H. Buetow, Identification of an NAD(P)H:quinone oxidoreductase polymorphism and its association with lung cancer and smoking, Pharmacogenetics 5 (1995) 199-206.
56. I. Cascorbi, J. Brockmöller, P.M. Mrozikiewicz, S. Bauer, R. Loddenkemper, I. Roots, Homozygous rapid arylamine N-acetyltransferase (NAT2) genotype as a susceptibility factor for lung cancer, Cancer Res. 56 (1996) 3961-3966.
57. F.F. Kadlubar, C.B. Frederick, C.C. Weis, T.V. Zenser, Prostaglandin endoperoxide synthetase-mediated metabolism of carcinogenic aromatic amines and their binding to DNA and protein, Biochem. Biophys. Res. Commun. 108 (1982) 253-258.
58. H. Sayo, M. Hosokawa, E. Lee, K. Kariya, M. Kohno, ESR studies on the oxidation of N,N-dimethyl-p-anisidine and its analogues catalyzed by myeloperoxidase, Biochem. Biophys. Acta 874 (1986) 187-192.
59. M.D. Corbett, B.R. Corbett, Nucleic acid binding of arylamines during the respiratory burst of human granulocytes, Chem. Res. Toxicol. 1 (1988) 356-363.
60. A.E. Cribb, M. Miller, A. Tesoro, S.P. Spielberg, Peroxidase-dependent oxidation of sulfonamides by monocytes and neutrophils from humans and dogs, Mol. Pharmacol. 38 (1991) 744-751.
61. J.-H. Shen, M. Wegenke, T. Wolff, Capability of human blood cells to form the DNA adduct, C8-(N2-aminofluorenyl)-deoxyguanosine-3′-5′-diphosphate from 2-aminofluorene, Carcinogenesis 11 (1990) 1441-1444.
62. M.A. Trush, L.E. Twerdok, R.L. Esterline, Comparison of oxidant activities and the activation of benzo(a)pyrene-7,8-dihydrodiol by polymorphonuclear leucocytes from human, rat and mouse, Xenobiotica 20 (1990) 925-932.
63. J.P. Uetrecht, N. Zahid, N-Chlorination and oxidation of procainamide by myeloperoxidase: toxicological implications, Chem. Res. Toxicol. 4 (1991) 218-222.
64. D.P. Banning, F. O'Farrell, N.J. Gooderham, Activation of a food-derived carcinogen 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline by rat pleural cavity inflammatory cells, Carcinogenesis 14 (1993) 2457-2462.
65. B.E. Svensson, K. Domeij, S. Lindvall, G. Rydell, Peroxidase and peroxidase-oxidase activities of isolated human myeloperoxidases, Biochem. J. 242 (1987) 673-680.
66. D. Thompson, D. Constantin-Teodosiu, K. Norbeck, B. Svensson, P. Moldeus, Metabolic activation of eugenol by myeloperoxidase and polymorphonuclear leukocytes, Chem. Res. Toxicol. 2 (1989) 186-192.
67. D.X. Lin, F.F. Kadlubar, Metabolic activation of carcinogen 4-aminobiphenyl by human neutrophil myeloperoxidase, Chin. J. Pharmacol. Toxicol. 8 (1994) 221-226.
68. S. Törnquist, M. Nicklasson, P. Söderkvist, L. Nybom, R. Toftgård, Bioavailability of benzo[a]pyrene deposited in the lung. Correlation with dissolution of urban air particles and covalently bound DNA adducts, Drug. Metab. Disp. 16 (1988) 842-847.
69. B.P. Dunn, S. Vedal, R.H.C. San, W.-F. Kwan, B. Nelems, D.A. Enarson, H.F. Stich, DNA adducts in bronchial biopsies, Int. J. Cancer 48 (1991) 485-492.