4-Aminobiphenyl and DNA reactivity: Case study within the context of the 2006 IPCS human relevance framework for analysis of a cancer mode of action for humans

Critical Reviews in Toxicology

Volumn 36, Issue 10, 2006, Pages 803-819

  Cohen, Samuel M ^a   Boobis, Alan R ^b   Meek, M E ^c   Preston, R Julian ^d   McGregor, Douglas B ^e  

^a UNIVERSITY OF NEBRASKA MEDICAL CENTER   (United States)

^b IMPERIAL COLLEGE LONDON   (United Kingdom)

^c HEALTH CANADA   (Canada)

^d U S ENVIRONMENTAL PROTECTION AGENCY   (United States)

^e Toxicology Evaluation Consultants   (United Kingdom)

Author keywords

Aromatic Animes; Hazard Characterization; Human Relevance; Mode of Action; Risk Assessment; Urinary Bladder

Indexed keywords

4 BIPHENYLAMINE; CARCINOGEN; DEOXYGUANOSINE; DNA;

BLADDER; CHEMICAL CARCINOGENESIS; DNA MODIFICATION; DOG; DOSE RESPONSE; ESTERIFICATION; GENOTOXICITY; HEALTH PROGRAM; HUMAN; HYDROXYLATION; INTERNATIONAL COOPERATION; LIVER; MALIGNANT NEOPLASTIC DISEASE; METABOLIC ACTIVATION; NONHUMAN; PREDICTION; QUALITATIVE ANALYSIS; QUANTITATIVE ANALYSIS; REVIEW; SAFETY; UROTHELIUM;

AMINOBIPHENYL COMPOUNDS; ANIMALS; CARCINOGENS; DNA; DOGS; HUMANS; MICE; MUTATION; NEOPLASMS; RABBITS; RATS; RISK ASSESSMENT; SPECIES SPECIFICITY; UROTHELIUM;

ANIMALIA; CANIS FAMILIARIS;

EID: 33751259351     PISSN: 10408444     EISSN: 15476898     Source Type: Journal    
DOI: 10.1080/10408440600977651     Document Type: Review

References (115)

1. al-Altrash, J., Zhang, Y.J., Lin, D., Kadlubar, F.F., and Santella, R.M. (1995). Quantitative immunohistochemical analysis of 4-aminobiphenyl-DNA cultured cells and mice: Comparison to gas chromatography/mass spectroscopy analysis. Chem. Res. Toxicol. 8:747-752.
2. Auerbach, O., and Garfinkel, L. (1989). Histologic changes in the urinary bladder in relation to cigarette smoking and use of artificial sweeteners. Cancer 64:987-987.
3. Besaratinia, A., Bates, S.E., and Pfeifer, G.P. (2002). Mutational signature of the proximate bladder carcinogen N-hydroxy-4-acetylaminobiphenyl: Inconsistency with the p53 mutational spectrum in bladder cancer. Cancer Res. 62:4331-4338.
4. Block, N.L., Sigel, M.M., Lynne, C.M., Ng, A.B., and Grosberg, R.A. (1978). The initiation, progress, and diagnosis of dog bladder cancer induced by 4-aminobiphenyl. Invest. Urol. 16:50-54.
5. Bonser, G.M. (1962). Precancerous changes in the urinary bladder. In The Morphological Precursor of Cancer, ed. L. Severi, p. 435. Perugia: University of Perugia.
6. Bookland, E.A., Reznikoff, C.A., Lindstrom, M., and Swaminathan, S. (1992a). Induction of thioguanine-resistant mutations in human uroepithelial cells by 4-aminobiphenyl and its N-hydroxy derivatives. Cancer Res. 52:1615-1621.
7. Bookland, E.A., Swaminathan, S., Oyasu, R., Gilchrist, K.W., Lindstrom, M., and Reznikoff, C.A. (1992b). Tumorigenic transformation and neoplastic progression of human uroepithelial cells after exposure in vitro to 4-aminobiphenyl or its metabolites. Cancer Res. 52:1606-1614.
8. Bryant, M.S., Vineis, P., Skipper, P.L., and Tannenbaum, S.R. (1988). Hemoglobin adducts of aromatic amines: Associations with smoking status and type of tobacco. Proc. Natl. Acad. Sci. USA 85:9788-9791.
9. Burger, M.S., Torino, J.L., and Swaminathan, S. (2001). DNA damage in human transitional cell carcinoma cells after exposure to the proximate metabolite of the bladder carcinogen 4-aminobiphenyl. Environ. Mol. Mutagen. 38:1-11.
10. Butler, M.A., Guengerich, F.P., and Kadlubar, F.F. (1989a). Metabolic oxidation of the carcinogens 4-aminobiphenyl and 4,4′-methylene-bis(2- chloroaniline) by human hepatic microsomes and by purified rat hepatic cytochrome P-450 monooxygenases. Cancer Res. 49:25-31.
11. Butler, M.A., Iwasaki, M., Guengerich, F.P., and Kadlubar, F.F. (1989b). Human cytochrome P-450PA (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 86:7696-7700.
12. Cairns, P., Proctor, A.J., and Knowles, M.A. (1991). Loss of heterozygosity at the RB locus is frequent and correlates with muscle invasion in bladder carcinoma. Oncogene 6:2305-2309.
13. 01 study: Introduction, objectives, and experimental design. J. Environ. Pathol. Toxicol. 3:1-7.
14. Cartwright, R.A., Rogers, H.J., Barham-Hall, D., Glashan, R.W., Ahmad, R.A., Higgins, E., and Kahn, M.A. (1982). Role of N-acetyltransferase phenotypes in bladder carcinogenesis: A pharmacogenetic epidemiological approach to bladder cancer. Lancet 16:842-846.
15. Cascorbi, I., Roots, I., and Brockmoller, J. (2001). Association of NAT1 and NAT2 polymorphisms to urinary bladder cancer: Significantly reduced risk in subjects with NAT1*10. Cancer Res. 61:5051-5056.
16. Castelao, J.E., Yuan, J.M., Skipper, P.L., Tannenbaum, S.R., Gago-Dominguez, M., Crowder, J.S., Ross, R.K., and Yu, M.C. (2001). Gender- and smoking-related bladder cancer risk. J. Natl. Cancer Inst. 93:538-545.
17. Chou, H.C., Lang, N.P., and Kadlubar, F.F. (1995). Metabolic activation of the N-hydroxy derivative of the carcinogen 4-aminobiphenyl by human tissue sulfotransferases. Carcinogenesis 16:413-417.
18. Clayson, D.B., Lawson, T.A., Santana, S., and Bonser, G.M. (1965). Correlation between the chemical induction of hyperplasia and of malignancy in the bladder epithelium. Br. J. Cancer 19:297.
19. Clayson, D.B., Lawson, T.A., and Pringle, J.A. (1967). The carcinogenic action of 2-aminodiphenylene oxide and 4-aminodiphenyl on the bladder and liver of C57 × IF mouse. Br. J. Cancer 1: 755.
20. Cohen, S.M. (1995). The role of urinary physiology and chemistry in bladder carcinogenesis. Food. Chem. Toxicol. 33:715-730.
21. 01 study. Toxicol. Appl. Pharmacol. 104:79-93.
22. Coghlin, J., Gann, P.H., Hammond, S.K., Skipper, P.L., Taghizadeh, K., Paul, M., and Tannenbaum, S.R. (1991). 4-Aminobiphenyl hemoglobin adducts in fetuses expsed to the tobacco smoke carcinogen. in utero. J. Natl. Cancer Inst. 83:274-280.
23. Cordon-Cardo, C., and Reuter, V.E. (1997). Alterations of tumor suppressor genes in bladder cancer. Semin. Diagn. Pathol. 14:123-132.
24. Curigliano, G., Zhang, Y.J., Wang, L.Y., Flamini, G., Alcini, A., Ratto, C., Giustacchini, M., Alcini, E., Cittadini, A., and Santella, R.M. (1996). Immunohistochemical quantitation of 4-aminobiphenyl-DNA adducts and p53 nuclear overexpression in T1 bladder cancer of smokers and nonsmokers. Carcinogensis 17:911-916.
25. Dang, L.N., and McQueen, C.A. (1999). Mutagenicity of 4-aminobiphenyl and 4-acetylbiphenyl in Salmonella typhimurium strains expressing different levels of N-acetyltransferase. Toxicol. Appl. Pharmacol. 159:77-82.
26. Deichmann, W.B., and MacDonald, W.E. (1968). The non-carcinogenicity of a single dose of 4-aminobiphenyl in the dog. Food Cosmet. Toxicol. 6:143.
27. Deichmann, W.B., Radomski, J.L., Anderson, W.A.D., Coplan, M.M., and Woods, F.M. (1958). The carcinogenic action of p-aminobiphenyl in the dog. Ind. Med. Surg. 27:25.
28. Deichmann, W.B., Radomski, J.L., Glass, E., Anderson, W.A., Coplan, M., and Woods, F.M. (1965). Synergism among oral carcinogens. Simultaneous feeding of four bladder carcinogens to dogs. Ind. Med. Surg. 34:640.
29. Del Santo, P., Moneti, G., Salvadori, M., Saltutti, C., Delle, R.A., and Dolara, P. (1991). Levels of the adducts of 4-aminobiphenyl to hemoglobin in control subjects and bladder carcinoma patients. Cancer Lett. 60:245-251.
30. Delclos, K.B., Miller, D.W., Lay, Jr., J.O., Casciano, D.A., Walker, R.P., Fu, P.P., and Kadlubar, F.F. (1987). Identification of C8-modified deoxyinosine and N2- and C8-modified deoxyguanosine as major products of the in vitro reaction of N-hydrozy-6-aminochrysene with DNA and the formation of these adducts in isolated rat hepatocytes treated with 6-nitrochrysene and 6-aminochrysene. Carcinogenesis 8:1703-1709.
31. Doerge, D.R., Churchwell, M.I., Marques, M.M., and Beland, F.A. (1999). Quantitative analyses of 4-aminobiphenyl-C8-deoxyguanosyl DNA adducts produced in vitro and in vivo using HPLC-ES-MS. Carcinogenesis 6:1055-1061.
32. Dooley, K.L., Stavenuiter, J.F., Westra, J.G., and Kadlubar, F.F. (1988). Comparative carcinogenicity of the food pyrolysis product, 2-amino-5- phenylpyridine, and the known human carcinogen, 4-aminobiphenyl, in the neonatal B6C3F1 mouse. Cancer Lett. 41:99-103.
33. Dooley, K.L., Von Tungeln, L.S., Bucci, T., Fu, P.P., and Kadlubar, F.F. (1992). Comparative carcinogenicity of 4-aminobiphenyl and the food pyrolysates, Glu-P-1, IQ, PhIP, and MeIQx in the neonatal B6C3F1 male mouse. Cancer Lett. 62:205-209.
34. Eaton, D.L., Gallagher, E.P., Bammler, T.K., and Kunze, K.L. (1995). Role of cytochrome P4501A2 in chemical carcinogenesis: Implications for human variability in expression and enzyme activity. Pharmacogenetics 5:259-274.
35. Faraglia, B., Chen, S.Y., Gammon, M.D., Zhang, Y., Teitelbaum, S.L., Neugut, A.I., Ahsan, H., Garbowski, G.C., Hibshoosh, H., Lin, D., Kadlubar, F.F., and Santella, R.M. (2003). Evaluation of 4-aminobiphenyl-DNA adducts in human breast cancer: The influence of tobacco smoke. Carcinogenesis 24:719-725.
36. Feng, Z., Hu, W., Rom, W.N., Beland, F.A., and Tang, M.S. (2002). N-Hydroxy-4-aminobiphenyl-DNA binding in human p53 gene: Sequence preference and the effect of C5 cytosine methylation. Biochemistry 41:6414-6421.
37. Flamini, G., Romano, G., Curigliano, G., Chiominto, A., Capelli, G., Boninsegna, A., Signorelli, C., Ventura, L., Santella, R.M., Sgambato, A., and Cittadini, A. (1998). 4-Aminobiphenyl-DNA adducts in laryngeal tissue and smoking habits: an immunohistochemical study. Carcinogenesis 19:353-357.
38. Flammang, T.J., and Kadlubar, F.F. (1986). Acetyl coenzyme A-dependent metabolic activation of N-hydroxy-3,2′-dimethyl-4-aminobiphenyl and several carcinogenic N-hydroxy arylamines in relation to tissue and species differences, other acyl donors, and arylhydroxamic acid-dependent acyltransferases. Carcinogensis 7:919-926.
39. Flammang, T.J., Couch, L.H., Levy, G.N., Weber, W.W., and Wise, C.K. (1992). DNA adduct levels in congenic rapid and slow acetylator mouse strains following chronic administration of 4-aminobiphenyl. Carcinogenesis 13:1887-1891.
40. Fletcher, K., Tinwell, H., and Ashby, J. (1998). Mutagenicity of the human bladder carcinogen 4-aminobiphenyl to the bladder of Muta™Mouse transgenic mice. Mutat. Res. 400:245-250.
41. Frederickson, S.M., Hatcher, J.F., Reznikoff, C.A., and Swaminathan, S. (1992). Acetyl transferase-mediated metabolic activation of N-hydroxy-4- aminobiphenyl by human uroepithelial cells. Carcinogenesis 13:955-961.
42. Fretland, A.J., Doll, M.A., Gray, K., Feng, Y., and Hein, D.W. (1997). Cloning, sequencing, and recombinant expression of NAT1, NAT2, and NAT3 derived from the C3H/HeJ (rapid) a A/HeJ (slow) acetylator inbred mouse: Functional characterization of the activation and deactivation of aromatic amine carcinogens. Toxicol. Appl. Pharmacol. 142:360-366.
43. 01 study: Summary and conclusions. J. Environ. Pathol. Toxicol. 3:179-183.
44. Gorrod, J.W., Carter, R.L., and Roe, F.J. (1968). Induction of hepatomas by 4-aminobiphenyl and three of its hydroxylated derivatives administered to newborn mice. J. Natl. Cancer lnst. 41:403.
45. Hammons, G.J., Guengerich, F.P., Weis, C.C., Beland, F.A., and Kadlubar, F.F. (1985). Metabolic oxidation of carcinogenic arylamines by rat, dog, and human hepatic microsomes and by purified flavin-containing and cytochrome P-450 monooxygenases. Cancer Res. 45:3578-3585.
46. Hatcher, J.F., Rao, K.P., and Swaminathan, S. (1993). Mutagenic activation of 4-aminobiphenyl and its N-hydroxy derivatives by microsomes from cultured human uroepithelial cells. Mutagenesis 8:113-120.
47. Hatcher, J.F., and Swaminathan, S. (1992). Microsome-mediated transacetylation and binding of N-hydroxy-4-aminobiphenyl to nucleic acids by hepatic and bladder tissues from dog. Carcinogenesis 13:1705-1711.
48. 32P-postlabeling analysis. Carcinogenesis 16:295-301.
49. Hatcher, J.F., and Swaminathan, S. (2002). Identification of N-(deoxyguanosin-8-yl)-4-azobiphenyl by (32)P-postlabeling analyses of DNA in human uroepithelial cells exposed to proximate metabolites of the environmental carcinogen 4-aminobiphenyl. Environ. Mol. Mutagen. 39:314-322.
50. Hein, D.W. (1988). Acetylator genotype and arylmaine-induced carcinogenesis. Biochem. Biophys. Acta 948:37-66.
51. Hein, D.W., Grant, D.M., and Sim, E. (2000). Arylamine N-acetyltransferase (NAT) nomenclature. http://www.louisville.edu/ medschool/pharmacology/NAT.html.
52. Hickman, E.S., Moroni, M.C., and Helin, K. (2002). The role of p53 and pRB in apoptosis and cancer. Curr. Opin. Genet. Dev. 12:60-66.
53. Hill, A.B. (1965). The environment and disease: Association or causation?. Proc. R. Soc. Med. 58:295-300.
54. Hughes, M.F., Smith, B.J., and Eling, T.E. (1992). The oxidation of 4-aminobiphenyl by horseradish peroxidase. Chem. Res. Toxicol. 5:340-345.
55. IARC. (1972). 4-Aminobiphenyl. IARC Monogr. Eval. Carcinogen. Risks Hum. 1:74-79.
56. IARC. (1986). Tobacco smoking. IARC Monogr. Eval. Carcinogen. Risks Hum. 38.
57. IARC. (1987). 4-Aminobiphenyl (Group 1). IARC Monogr. Eval. Carcinogen. Risks Hum. Suppl. 7:91-92.
58. Ioachim, E., Charchanti, A., Stavropoulos, N.E., Skopelitou, A., Athanassiou, E.D., and Agnantis, N.J. (2000). Immunohistochemical expression of retinoblastoma gene product (Rb), p53 protein, MDM2, c-erbB-2, HLA-DR and proliferation indices in human urinary bladder carcinoma. Histol. Histopathol. 15:721-727.
59. Ishikawa, J., Xu, H.J., Hu, S.X., Yandell, D.W., Maeda, S., Kamidono, S., Benedict, W.F., and Takahashi, R. (1991). Inactivation of the retinoblastoma gene in human bladder and renal cell carcinomas. Cancer Res. 51:5736-5743.
60. Kadlubar, F.F., Miller, J.A., and Miller, E.C. (1977). Hepatic microsomal N-glucuronidation and nucleic acid binding of N-hydroxy arylamines in relation to urinary bladder carcinogenesis. Cancer Res. 37:805-814.
61. Kadlubar, F.F., Frederick, C.B., Weis, C.D., and Zenser, T.V. (1982). Prostaglandin endoperoxide synthetase-mediated metabolism of carcinogenic aromatic amines and their binding to DNA and protein. Biochem. Biophys. Res. Commun. 108:253-258.
62. Kadlubar, F.F., Dooley, K.L., Teitel, C.H., Roberts, D.W., Benson, R.W., Butler, M.A., Bailey, J.R., Young, J.F., Skipper, P.W., and Tannenbaum, S.R. (1991). Frequency of urination and its effects on metabolism, pharmacokinetics, blood hemoglobin adduct formation, and liver and urinary bladder DNA adduct levels in beagle dogs given the carcinogen 4-aminobiphenyl. Cancer Res. 51:4371-4377.
63. Kimura, S., Kawabe, M., Ward, J.M., Morishima, H., Kadlubar, F.F., Hammons, G.J., Fernandez-Salguero, P., and Gonzalez, F.J. (1999). CYP1A2 is not the primary enzyme responsible for 4-aminobiphenyl-induced hepatocarcinogenesis in mice. Carcinogenesis 20:1825-1830.
64. Koss, L.G., Myron, R., Melamed, M.R., and Kelly, R.E. (1969). Further cytologic and histologic studies of bladder lesions in workers exposed to para-aminodiphenyl: Progress report. J. Natl. Cancer Inst. 43:233.
65. Koss, L.G., Myron, R., Melamed, M.R., Ricci, A., Melick, W.F., and Kelly, R.E. (1965). Carcinogenesis in the human urinary bladder. Observations after exposure to para-aminodiphenyl. New Engl. J. Med. 272:767.
66. Kriek, E. (1992). Fifty years of research on N-acetyl-2-aminofluorene, one of the most versatile compounds in experimental research. J. Cancer Res. Clin. Oncol. 118:481-489.
67. Lakshmi, V.M., Mattammal, M.B., Zenser, T.V., and Davis, B.B. (1990). Mechanism of peroxidative activation of the bladder carcinogen 2-amino-4-(5-nitro-2-furyl)-thiazole (ANFT): Comparison with benzidine. Carcinogenesis 11:1965-1970.
68. Lang, M., and Pelkonen, O. (1999). Metabolism of xenobiotics and chemical carcinogenesis. IARC Sci. Publ. 13-22.
69. Littlefield, N.A., Farmer, J.H., Gaylor, D.W., and Sheldon, W.G. (1979). Effects of dose and time in a long-term, low-dose carcinogenic study. J. Environ. Pathol. Toxicol. 3:17-34.
70. Logothetis, C.J., Xu, H.J., Ro, J.Y., Hu, S.X., Sahin, A., Ordonez, N., and Benedict, W.F. (1992). Altered expression of retinoblastoma protein and known prognostic variables in locally advanced bladder cancer. J. Natl. Cancer. Inst. 84:1256-1261.
71. Lower, Jr., G.M., Nelson, C.E., Wolf, H., Gamsky, T.E., and Bryan, G.T. (1979). N-Acetyltransferase phenotype and risk in urinary bladder cancer:approaches in molecular epidemiology. Preliminary results in Sweden and Denmark. Environ. Health Perspect. 29:71-79.
72. Lu, M.L., Wikman, F., Orntoft, T.F., Charytonowicz, E., Rabbani, F., Zhang, Z., Dalbagni, G., Pohar, K.S., Yu, G., and Cordon-Cardo, C. (2002). Impact of alterations affecting the p53 pathway in bladder cancer on clinical outcome, assessed by conventional and array-based methods. Clin. Cancer Res. 8:171-179.
73. Manjanatha, M.G., Li, E.E., Fu, P.P., and Heflich, R.H. (1996). H- and K-ras mutational profiles in chemically induced liver tumours from B6C3F1 and CD-1 mice. J. Toxicol. Environ. Health 47:195-208.
74. Martone, T., Airoldi, L., Magagnotti, C., Coda, R., Randone, D., Malaveille, C., Avanzi, G., Merletti, F., Hautefeuille, A., and Vineis, P. (1998). 4-Aminobiphenyl-DNA adducts and p53 mutations in bladder cancer. Int. J. Cancer 75:512-516.
75. Mattano, S.S., Land, S., King, C.M., and Weber, W.W. (1989). Purification and biochemical characterization of hepatic arylamine N-acetyltransferase from rapid and slow acetylator mice: Identify with arylhydroxamic acid N,O-acyltransferase and N-hydroxyarylamine O-Acetyltransferase. Mol. Pharmacol. 68:599-609.
76. McQueen, C.A., Chau, B., Erickson, R.P., Tjalkens, R.B., and Philbert, M.A. (2003). The effects of genetic variation in N-acetyltransferases on 4-aminobiphenyl genotoxicity in mouse liver. Chem. Biol. Interact. 146:51-60.
77. Melamed, M.R., Koss, L.G., Ricci, A., and Whitmore, W.F. (1960). Cytohistological observations on developing carcinoma of urinary bladder in man. Cancer (Phila.) 13:67.
78. Melick, W.F., Escue, H.M., Naryka, J.J., Mezera, R.A., and Wheeler, E.R. (1955). The first reported cases of human bladder tumors due to a new carcinogen-Xenylamine. J. Urol. (Baltimore) 74: 760.
79. Melick, W.F., Naryka, J.J., and Kelly, R.E. (1971). Bladder cancer due to exposure to para-aminobiphenyl: A 17-year follow-up. J. Urol. (Baltimore) 106:220.
80. Merck Veterinary Manual, 1998.
81. Miller, J.C., and Miller, E.C. (1977). Ultimate chemical carcinogens as reactive mutagenic eletrophiles. In Origins of Human Cancer, eds. H.H. Hiatt, J.D. Watson, and J.A. Winsten, pp. 605-627. Cold Spring Harbor, NY: Cold Spring Harbor Laboratory.
82. Miller, J.A., Wyatt, C.S., Miller, E.C., and Hartmann, H.A. (1961). The N-hydroxylation of 4-acetylaminobiphenyl by the rat and dog and the strong carcinogenicity of N-hydroxy-4-acetylaminobiphenyl in the rat. Cancer Res 21:1465.
83. Oda, Y. (2004). Analysis of the involvement of human N-acetyltransferase 1 in the genotoxic activation of bladder carcinogenic arylamines using a SOS/umu assay system. Mutat. Res. 554:399-406.
84. Oscarson, M., Ingelman-Sundberg, M., Daly, A.K., and Nebert, D.W. Human Cytochrome P450 (CYP) Allele Nomenclature Committee. http//www.imm.ki.se/ CYPalleles/
85. Parsons, B.L., Culp, S.J., Manjanatha, M.G., and Heflich, R.H. (2002). Occurrence of H-ras codon 61 CAA to AAA mutation during mouse liver tumor progression. Carcinogenesis 23:943-948.
86. Parsons, B.L., Beland, F.A., Von Tungeln, L.S., Delongchamp, R.R., Fu, P., and Heflich, R.H. (2005). Levels of 4-aminobiphenyl-induced somatic H-ras mutation in mouse liver correlate with potential for liver tumor development. Mol. Carcinogen. 42:193-201.
87. Pauli, B.U., Alroy, J., and Weinstein, R.S. (1983). The ultrastructure and pathobiology of urinary bladder cancer. In The Pathology of Bladder Cancer, Vol. II, eds. G.T. Bryan and S.M. Cohen pp. 41-140. Boca Raton, FL: CRC Press.
88. Poirier, M.C., and Beland, F.A. (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.
89. Poirier, M.C., Fullerton, N.F., Smith, B.A., and Beland, F.A. (1995). DNA adduct formation and tumorigenesis in mice during the chronic administration of 4-aminobiphenyl at multiple dose levels. Carcinogenesis 16:2917-2921.
90. Presti, J.C., Reuter, V.E., Galan, T., Fair, W.R., and Cordon-Cardo, C. (1991). Molecular genetic alterations in superficial and locally advanced human bladder cancer. Cancer Res. 51:5405-5409.
91. Primdahl, H., von der, M., Christensen, M., Wolf, H., and Orntoft, T.F. (2000). Allelic deletions of cell growth regulators during progression of bladder cancer. Cancer Res. 60:6623-6629.
92. Reznikoff, C.A., Loretz, L.J., Johnson, M.D., and Swaminathan, S. (1986). Quantitative assessments of the cytotoxicity of bladder carcinogens towards cultured normal human uroepithelial cells. Carcinogenesis 7:1625-1632.
93. Roberts, D.W., Benson, R.W., Groopman, J.D., Flammang, T.J., Nagle, W.A., Moss, A.J., and Kadlubar, F.F. (1988). Immunochemical quantitation of DNA adducts derived from the human bladder carcinogen 4-aminobiphenyl. Cancer Res. 48:6336-6342.
94. Sachse, C., Bhambra, U., Smith, G., Lightfoot, T.J., Barrett, J.H., Scollay, J., Garner, R.C., Boobis, A.R., Wolf, C.R., Gooderham, N.J., and Colorectal Cancer Study Group. (2003). Polymorphisms in the cytochrome P450 CYP1A2 gene (CYP1A2) in colorectal cancer patients and controls: Allele frequencies, linkage disequilibrium and influence on caffeine metabolism. Br. J. Clin. Pharmacol 55:68-76.
95. Sarkar, M.A., Nseyo, U.O., and Zhong, B.-Z. (2002). Mutagenic outcome of the urinary carcinogen 4-aminobiphenyl is increased in acidic pH. Environ. Toxicol. Pharmacol. 11:23-26.
96. Schieferstein, G.J., Littlefield, N.A., Gaylor, D.W., Sheldon, W.G., and Burgers, G.T. (1985). Carcinogenesis of 4-aminobiphenyl in BALB/cStCrlfC3Hf/Nctr mice. Eur. J. Cancer Clin. Oncol. 21:865-873.
97. Schroeder, J.C., Conway, K., Li, Y., Mistry, K., Bell, D.A., and Taylor, J.A. (2003). p53 mutations in bladder cancer: Evidence for exogenous versus endogenous risk factors. Cancer Res. 63:7530-7538.
98. Sesardic, D., Boobis, A.R., Edwards, R.J., and Davies, D.S. (1988). A form of cytochrome P450 in man, orthologous to form d in the rat, catalyses the O-deethylation of phenacetin and is inducible by cigarette smoking. Br. J. Clin. Pharmacol. 26:363-372.
99. Skipper, P.L., Tannenbaum, S.R., Ross, R.K., and Yu, M.C. (2003). Nonsmoking-related arylamine exposure and bladder cancer risk. Cancer Epidemiol. Biomarkers Prev. 12:503-507.
100. Smith, B.J., Curtis, J.F., and Eling, T.E. (1991). Bioactivation of xenobiotics by prostaglandin H synthase. Chem. Biol. Interact. 79:245-264.
101. Sonich-Mullin, C., Fielder, R., Wiltse, J., Baetcke, K., Dempsey, J., Fenner-Crisp, P., Grant, D., Hartley, M., Knaap, A., Krose, D., Mangelsdorf, I., Meek, E., Rice, J.M., and Younes, M. (2001). IPCS conceptual framework for evaluating a mode of action for chemical carcinogenesis. Regul. Toxicol. Pharmacol. 34:146-152.
102. Swaminathan, S.A. (1992). Metabolism and nucleic acid finding of N-hydroxy-4-acetylaminobiphenyl and N-acetyoxy-4-acetylaminibiphenyl bu cultured human uroepithelial cells. Cancer Res 52:3286-3294.
103. 32P-postlabelling and subsequent thin-layer and high-pressure liquid chromatography. Carcinogenesis 11:639-646.
104. Tiguert, R., Bianco, F.J., Oskanian, P., Li, Y., Grignon, D.J., Wood, D.P., Pontes, J.E., and Sarkar, F.H. (2001). Structural alteration of p53 protein in patients with muscle invasive bladder transitional cell carcinoma. J. Urol. 166:2155-2160.
105. Tsuneoka, Y., Dalton, T.P., Miller, M.L., Clay, C.D., Shertzer, H.G., Talaska, G., Medvedovic, M., and Nebert, D.W. (2003). 4-Aminobiphenyl-induced liver and urinary bladder DNA adduct formation in Cyp1a2(-/-) and Cyp1a2(+/+) mice. J. Natl. Cancer Inst. 95:1227-1237.
106. Underwood, P.M., Zhou, Q., Jaeger, M., Reilman, R., Pinney, S., Warshawsky, D., and Talaska, G. (1997). Chronic, topical administration of 4-aminobiphenyl induces tissue-specific DNA adducts in mice. Toxicol. Appl. Pharmacol. 144:325-331.
107. 8-ABP lesion in single-stranded DNA. Carcinogenesis 18:2403-2414.
108. Vineis, P., Caporaso, N., Tannenbaum, S.R., Skipper, P.L., Glogowski, J., Bartsch, H., Coda, M., Talaska, G., and Kadlubar, F.F. (1990). Acetylation phenotype, carcinogen-hemoglobin adducts, and cigarette smoking. Cancer Res. 50:3002-3004.
109. Von Tungeln, L.S., Bucci, T.J., Hart, R.W., Kadlubar, F.F., and Fu, P.P. (1996). Inhibitory effect of caloric restriction on tumorigenicity induced by 4-aminobiphenyl and 2-amino-1-methyl-6-phenylimidazo-[4,5-b]pyridine (PhIP) in the CD1 newborn mouse bioassay. Cancer Lett. 104:133-136.
110. Vousden, K.H., and Lu, X. (2002). Live or let die: The cell's response to p53. Nat. Rev. Cancer 2:594-604.
111. Walpole, A.L., Williams, M.H., and Roberts, D.C. (1952). The carcinogenic action of 4-aminodiphenyl and 3:2′-dimethyl-4-aminodiphenyl. Br. J. Ind. Med. 9:255.
112. Walpole, A.L., Williams, M.H.C., and Roberts, D.C. (1954). Tumours of the urinary bladder in dogs after ingestion of 4-aminodiphenyl. Br. J. Ind. Med 11:105.
113. Weston, A., Caporaso, N.E., Taghizadeh, K., Hoover, R.N., Tannenbaum, S.R., Skipper, P.L., Resau, J.H., Trump, B.F., and Harris, C.C. (1991).Measurement of 4-aminobiphenyl-hemoglobin adducts in lung cancer cases and controls. Cancer Res. 51:5219-5223.
114. Wright, C., Thomas, D., Mellon, K., Neal, D.E., and Horne, C.H. (1995). Expression of retinoblastoma gene product and p53 protein in bladder carcinoma: Correlation with Ki67 index. Br. J. Urol. 75:173-179.
115. Wu, X.R., Lin, J.H., Walz, T., Haner, M., Yu, J., Aebi, U., and Sun, T.T. (1994). Mammalian uroplakins. A group of highly conserved urothelial differentiation-related membrane proteins. J. Biol. Chem. 269:13716-13724.