Dephenylation of the rubber chemical N-phenyl-2-naphthylamine to carcinogenic 2-naphthylamine: A classical problem revisited

Critical Reviews in Toxicology

Volumn 37, Issue 7, 2007, Pages 553-566

  Weiss, Tobias ^a   Brüning, Thomas ^a   Bolt, Hermann M ^b  

^a RUHR UNIVERSITY BOCHUM   (Germany)

^b LEIBNIZ RESEARCH CENTRE FOR WORKING ENVIRONMENT AND HUMAN FACTORS   (Germany)

Author keywords

2 Naphthylamine; Bladder cancer; Carcinogenicity; Dephenylation; N phenyl 2 naphthylamine; Risk assessment; Rubber chemicals

Indexed keywords

2 METHYLANILINE; 2 NAPHTHYLAMINE; CARCINOGEN; CLASTOGEN; CYTOCHROME P450 ISOENZYME; IMINE; N PHENYL 2 NAPHTHYLAMINE; NAPHTHALENE DERIVATIVE; PHENOL DERIVATIVE; QUINONE DERIVATIVE; RUBBER; UNCLASSIFIED DRUG;

ANGIOSARCOMA; BIOASSAY; BLADDER CANCER; BLADDER CARCINOGENESIS; BREAST FIBROADENOMA; CANCER RISK; CARCINOGENICITY; CHEMICAL CARCINOGENESIS; CHEMICAL REACTION; DEPHENYLATION; EPIDEMIOLOGICAL DATA; GENOTOXICITY; HUMAN; HYDROLYSIS; HYPOPHYSIS ADENOMA; IN VITRO STUDY; IN VIVO STUDY; KIDNEY SARCOMA; LEUKEMIA; LIVER SARCOMA; LUNG SARCOMA; METABOLISM; MUTAGEN TESTING; OCCUPATIONAL CANCER; OCCUPATIONAL CARCINOGENESIS; OCCUPATIONAL EXPOSURE; OXIDATION; QUANTITATIVE ANALYSIS; REVIEW; THYROID CANCER; URINE LEVEL;

2-NAPHTHYLAMINE; ANIMALS; CARCINOGENS, ENVIRONMENTAL; DOGS; HUMANS; INDUSTRY; MICE; OCCUPATIONAL EXPOSURE; OXIDATION-REDUCTION; RATS; RISK ASSESSMENT; RUBBER;

ANIMALIA; CANIS FAMILIARIS;

EID: 34547691131     PISSN: 10408444     EISSN: 15476898     Source Type: Journal    
DOI: 10.1080/10408440701419637     Document Type: Review

References (76)

1. American Conference of Governmental Industrial Hygienists. (2001). N-Phenyl-beta-naphthylamine: TLV® Chemical Substances 7th Edition Documentation. American Conference of Governmental Industrial Hygienists, Cincinnati, OH. ACGIH Publication 7DOC-453.
2. Anderson, M.M., Mitchum, R.K., and Beland, F.A. (1982). Hepatic microsomal metabolism and macromolecular binding of the antioxidant, N-phenyl-2-naphthylamine. Xenobiotica 12:31-43.
3. Anderson, D., and Styles, J.A. (1978). The bacterial mutation test. Six tests for carcinogenicity. Br. J. Cancer 37(6):924-30.
4. Anderson, B.E., Zeiger, E., Shelby, M.D., Resnick, M.A., Gulati, D.K., Ivett, J.L., and Loveday, K.S. (1990). Chromosome aberration and sister chromatid exchange test results with 42 chemicals. Environ. Mol. Mutagen. 16(Suppl. 18):55-137.
5. Bartsch, H., Malaveille, C., Camus, A.M., Martel-Planche, G., Brun, G., Hautefeuille, A., Sabadie, N., Barbin, A., Kuroki, T., Drevon, C., Piccoli, C., and Montesano, R. (1980). Validation and comparative studies on 180 chemicals with S. typhimurium strains and V79 Chinese hamster cells in the presence of various metabolizing systems. Mutat. Res. 76(1):1-50.
6. Batten, B.L., and Hathway, D.E. (1977). Dephenylation of N-phenyl-2-naphthylamine in dogs and its possible oncogenic implications. Br. J. Cancer 35:342-346.
7. Bolt, H.M. (1998). The carcinogenic risk of ethene (ethylene). Toxicol Pathol. 26(3):454-456.
8. Bolt, H.M., and Filser, J.G. (1984). Olefinic hydrocarbons. A first risk estimate for ethene. Toxicol. Pathol. 12:101-105.
9. Bolt, H.M., and Filser, J.G. (1987). Kinetics and disposition in toxicology. Example: carcinogenic risk estimate for ethylene. Arch. Toxicol. 60:73-76.
10. Bonser, G.M., Clayson, D.B., and Jull, J.W. (1951). An experimental inquiry into the cause of industrial bladder cancer. Lancet I(6677):286-288.
11. Bonser, G.M., Clayson, D.B., Jull, J.W., and Pyrah, L.N. (1952). The carcinogenic properties of 2-amino-1-naphthol hydrochloride and its parent amine 2-naphthylamine. Br. J. Cancer 6:412-424.
12. Booth, J., Boyland, E., and Manson, D. (1955). Metabolism of polycyclic compounds. 9. Metabolism of 2-naphthylamine in rat tissue slices. Biochem J. 60(1):62-71.
13. Boyd, J.A., and Eling, T.E. (1987). Prostaglandin H synthase-catalyzed metabolism and DNA binding of 2-naphthylamine. Cancer Res. 47(15):4007-4014.
14. Boyland, E., and Manson, D. (1966a). The biochemistry of aromatic amines. Biochem. J. 99:189-199.
15. Boyland, E., and Manson, D. (1966b). The biochemistry of aromatic amines. The metabolism of 2-naphthylamine and 2-naphthylhydroxylamine derivatives. Biochem. J. 101:84-102.
16. Boyland, E., Dukes, C.E., and Grover, P.I. (1963). Carcinogenicity of 2-naphthylhydroxylamine and 2-naphthylamine. Br. J. Cancer 17:79-84.
17. Brill, E. (1977). The role of dog bladder mucosa in the N-oxidation of arylamines. Res. Commun. Chem. Pathol. Pharmacol. 16(1):73-84.
18. Brill, E., and Radomski, J.L. (1967). Studies on the N-hydroxylation and the photochemical oxidation of 2-naphthylamine. In: Bladder Cancer, a Symposium, pp. 90-97. Aesculapius, Birmingham, AL.
19. Case, R.A., and Hosker, M.E. (1954). Tumour of the urinary bladder as an occupational disease in the rubber industry in England and Wales. Br. J. Prev. Soc. Med. 8:9-50.
20. Centers for Disease Control. (1976). Current Intelligence Bulletin 16. December 17. Centers for Disease Control, Atlanta, GA.
21. Conzelman, G.M., and Moulton, J.E. (1972). Dose-response relationships of the bladder tumorigen 2-naphthylamine: A study in Beagle dogs. J. Natl. Cancer Inst. 49:193-205.
22. Degen, G.H., Schlattjan, J.H., Mähler, S., Föllmann, W., and Golka, K. (2004). Comparative metabolic activation of benzidine and N-acetylbenzidine by prostaglandin H synthase. Toxicol. Lett. 151:135-142.
23. Deichmann, W.B., and Radomski, J.L. (1969). Carcinogenicity and metabolism of aromatic amines in the dog. J. Natl. Cancer Inst. 43(1):263-269.
24. Deutsche Forschungsgemeinschaft (1977). Phenyl-2-naphthylamin. In: Henschler D, ed., Toxikologisch-arbeitsmedizinische Begründungen von MAK-Werten, pp. 1-6. VCH Verlag, Weinheim.
25. Druckrey, H., and Küpfmüller, K. (1948). Quantitative Analyse der Krebsentstehung. Z. Naturforsch. 3:254.
26. Föllmann, W., Mähler, S., Schuhmacher, U.S., and Guhe, C. (1997). An in vitro model of the urinary bladder: cultured porcine urinary bladder epithelial cells. Toxicol. In Vitro 11:427-433.
27. Gehrmann, G.H., Foulger, J.H., and Fleming, A.J. (1949). Occupational carcinoma of the bladder. Proceedings of the 9th ICOH Congress, London, Section D, Session VIII, pp. 472-475 [available through http://www.cdldevoto.it/library accessed April 18, 2007].
28. Golka, K., Wiese, A., Assenato, G., and Bolt, H.M. (2004). Occupational exposure and urological cancer. World J. Urol. 21:282-291.
29. Gorrod, L.W., and Manson, D. (1986). The metabolism of aromatic amines. Xenobiotica 16:933-955.
30. Green, U., Holste, J., and Spikermann, A.R. (1979). A comparative study of the chronic effects of magenta, paramagenta, and phenylbeta-naphthylamine in Syrian golden hamsters. J. Cancer Res. Clin. Oncol. 95:51-55.
31. Green, M.D., and Tephly, T.R. (1987). N-glucuronidation of carcinogenic aromatic amines catalyzed by rat hepatic microsomal preparations and purified rat liver uridine 5′-diphosphate-glucuronosyltransferases. Cancer Res. 47(8):2028-2031.
32. Guhe, C., Degen, G.H., Schuhmacher, U.S., Kiefer, F., and Föllmann, W. (1996). Drug metabolizing enzyme activities in porcine urinary bladder epithelial cell cultures (PUBEC). Arch. Toxicol. 70:599-606.
33. Hamm, T.E., Guest, D., and Dent, J.G. (1984). Chronic toxicity and oncogenicity bioassay of inhaled ethylene in Fischer-344 rats. Fundam. Appl. Toxicol. 4:473-478.
34. 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(8):3578-3585.
35. HVBG. (2006). Gefahrstoffliste 2006. BGIA Report 1/2006. Hauptverband der gewerblichen Berufsgenossenschaften, Sankt Augustin, Germany. ISBN 3-88383-700-8.
36. IARC. (1974). 2-Naphthylamine. IARC Monogr Eval Carcinog Risk Hum. 4:97-111.
37. IARC. (1978). N-Phenyl-2-naphthylamine. IARC Monogr Eval Carcinog Risk Hum. 16:325-341.
38. IARC. (1987). N-Phenyl-2-naphthylamine. IARC Monogr Eval Carcinogen. Risk Hum. Suppl. 7:318.
39. IARC. (1994). Ethylene oxide. IARC Monogr. Eval. Carcinogen. Risk Hum. 60:73-159.
40. Innes, J.R., Ulland, B.M., Valerio, M.G., Petrucelli, L., Fishbein, L., Hart, E.R., Pallotta, A.J., Bates, R.R., Falk, H.L., Gart, J.J., Klein, M., Mitchell, I., and Peters, J. (1969). Bioassay of pesticides and industrial chemicals for tumorigenicity in mice: A preliminary note. J. Natl. Cancer Inst. 42(6):1101-1114.
41. 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(3):805-814.
42. Kawachi, T., Yahagi, T., Kada, T., Tazima, Y., Ishidate, M., Sasaki, M., and Sugiyama, T. (1980). Cooperative programme on short-term assays for carcinogenicity in Japan. IARC Sci. Publ. 27:323-330.
43. Ketkar, B., and Mohr, U. (1982). The chronic effects of magenta, paramagenta and phenyl-β-naphthylamine in rats after intragastric administration. Cancer Lett. 16:203-206.
44. Korallus, U. (1998). Tumoren der Harnwege bei Beschäftigten in der deutschen Gummi-Industrie - Ein arbeitsmedizinisches Altlastenproblem. Zbl. Arbeitsmed. 48:266-274.
45. Kummer, R., and Tordoir, W.F. (1975). Phenyl-betanaphthylamine (PBNA), another carcinogenic agent? T. Soc. Geneesk. 53:415-419.
46. Laham, S., and Potvin, M. (1983). Biological conversion of N-phenyl-2-naphthylamine to 2-naphthylamine in the Sprague-Dawley rat. Drug Chem. Toxicol. 6:295-309.
47. Laham, S., and Potvin, M. (1984). Comparative N-dephenylation of N-phenyl-2-naphthylamine in Sprague-Dawley rats and New Zealand white rabbits. Chemosphere 13(5-6):657-667.
48. Lakshimi, V.M., Zenser, T.V., and Davis, B.B. (1998). N′-(3′-Monophosphato-deoxyguanosin-8-yl)-N- acetylbenzidine formation by peroxidative metabolism. Carcinogenesis 19:911-917.
49. Lewalter, J., and Gries, W. (2001). Haemoglobin adducts of aromatic amines. In: Deutsche Forschungsgemeinschaft, Angerer J, Schaller KH, eds., Analysis of Hazardous Substances in Biological Materials, Vol. 7, Wiley-VCH, 191-219.
50. Lueersen, L., Wellner, T., Angerer, J., Drexler, H., and Korinth, G. (2005). Investigation of the penetration of aromatic amines through the human skin in vitro. International Conference on Occupational and Environmental Exposures of Skin to Chemicals (OEESC), Stockholm, Sweden [Abstract: http://www.cdc.gov/niosh/topics/skin/OEESC2/AbPost048Lueersen.html accessed April 18, 2007].
51. Moore, R.M., Woolf, B.S., Stein, H.P., Thomas, A.W., and Finklea, J.F. (1977). Metabolic precursors of a known human carcinogen. Science 195:344.
52. Munn, A. (1974). Bladder cancer and carcinogenic impurities in rubber additives. Rubber Ind. 8:19-21.
53. Norpoth, K., and Woitowitz, H.J. (1991). Beruflich verursachte Tumoren. Grundlagen zur Entscheidung zur BK-Verdachtsanzeige. Deutscher Ärzteverlag, Köln, Germany.
54. NTP. (1988). National Toxicology Program - Toxicology and Carcinogenesis Studies of N-Phenyl-2-naphthylamine (CAS No. 135-88-6) in F344/N Rats and B6C3F1 Mice (Feed Studies). Natl. Toxicol. Program Tech. Rep. Ser. 333:1-168.
55. Pliss, G.B. (2004). Experimental study of ortho-toluidine carcinogenicity Vopr Onkol. 50:567-71. [Russian].
56. Pliss, G.B., and Zabezhinskii, M.A. (1983). Carcinogenic risk of Neozone D (N-phenyl-2-naphthylamine) Vopr. Onkol. 29(7):91-3. [Russian].
57. Pliss, G.B., Vlasov, N.N., and Zabezhinskii, M.A. (1991). The carcinogenic and anticarcinogenic properties of neozon D. Vopr Onkol 37:60-64. [Russian].
58. Poupko, J.M., Hearn, W.L., and Radomski, J.L. (1979). N-Glucuronidation of N-hydroxy aromatic amines: A mechanism for their transport and bladder-specific carcinogenicity. Toxicol. Appl. Pharmacol. 50(3):479-484.
59. Rannug, A., Rannug, U., and Ramel, C. (1984). Genotoxic effects of additives in synthetic elastomers with special consideration to the mechanism of action of thiurams and dithiocarbamates. Prog. Clin. Biol. Res. 141:407-419.
60. Ringe, D., Turesky, R.J., Skipper, P.L., and Tannenbaum, S.R. (1988). Structure of the single stable hemoglobin adduct formed by 4-aminobiphenyl in vivo. Chem. Res Toxicol. 1(1):22-24.
61. Schmidt, E., Lohs, K.H., and Otto, J. (1983). Industrietoxikologische Bewertung von Vulkanisationsdämpfen unter besonderer Berücksichtigung stickstoffhaltiger Alterungsschutzmittel. Z. Ges. Hyg. 28:442-446.
62. Scott, T.S. (1962). Carcinogenic and chronic toxic hazards of aromatic amines. Elsevier, New York.
63. Skipper, P.L., and Tannenbaum, S.R. (1990). Protein adducts in the molecular dosimetry of chemical carcinogens. Carcinogenesis 11(4):507-518.
64. Sofuni, T., Matsuoka, A., Sawada, M., Ishidate, M. Jr., Zeiger, E., and Shelby, M.D. (1990). A comparison of chromosome aberration induction by 25 compounds tested by two Chinese hamster cell (CHL and CHO) systems in culture. Mutat. Res. 241(2):175-213.
65. Sorahan, T., Hamilton, L., and Jackson, J.R. (2000). A further cohort study of workers employed at a factory manufacturing chemicals for the rubber industry, with special reference to the chemicals 2-mercaptobenzothiazole (MBT), aniline, phenyl-beta-naphthylamine and o-toluidine. Occup. Environ. Med. 57(2):106-115.
66. Takemura, N., and Shimizu, H. (1978). Mutagenicity of some aromatic amino and nitro compounds. Mutat. Res. 54(2):256-257.
67. Tolbert, P.E. (1997). Oils and cancer. Cancer Causes Control 8:386-405.
68. Troll, W., and Nelson, N. (1961). N-Hydroxy-2-naphthylamine, a urinary metabolite of 2-naphthylamine in man and dog. Fed. Proc. 20:41.
69. Veys, C.A. (1996). Bladder cancer in rubber workers, a PBNA exposed workforce. Progress in Rubber and Plastics Technology 12:258-273.
70. Walker, V.E., Wu, K.Y., Upton, P.B., Ranasinghe, A., Schelle, N., Cho, M.H., Vergnes, J.S., Skopek, T.R., and Swenberg, J.A. (2000). Biomarkers of exposure and effect as indicators of potential carcinogenic risk arising from in vivo metabolism of ethylene to ethylene oxide. Carcinogenesis 21(9):1661-1669.
71. Wang, H.W., Wang, D., and Dzeng R.W. (1984a). Carcinogenicity of N-phenyl-1-naphthylamine and N-phenyl-2-naphthylamine in mice. Cancer Res. 44:3098-3100.
72. Wang, H.W., You, Y.J., Qu, Y.H., Wang, Y.F., Wang, D., Long, Y.M., and Ni, J.A. (1984b). Investigation of cancer epidemiology and study of carcinogenic agents in the Shanghai rubber industry. Cancer Res. 44:3101-3105.
73. Wang, J., DeMaio, W., Chandrasekaran, A., Shen, L., Bach, A.C. 2nd, Scatina, J., and Talaat, R. (2006). Mechanism study of Ndephenylation mediated through a N-para-hydroxy metabolite. Curr. Drug Discov. Technol. 3(2):101-114.
74. Weiss, T. (2005). Entwicklung und Anwendung analytischer Methoden zum Biologischen Monitoring und Biochemischen Effektmonitoring von aromatischen Aminen im Rahmen arbeits- und umweltmedizinischer Fragestellungen. Dissertation, Universität Erlangen-Nürnberg, Germany. [Available through: http://www.opus.ub.uni-erlangen.de/opus/volltexte/2005/273/pdf/ DissertationTobiasWeiss-21112005.pdf accessed April 18, 2007].
75. Zeiger, E., Anderson, B., Haworth, S., Lawlor, T., and Mortelmans, K. (1988). Salmonella mutagenicity tests: IV. Results from the testing of 300 chemicals. Environ Mol. Mutagen. 11(Suppl. 12): 1-157.
76. Zenser, T.V., Lakshimi, V.M., Hsu, F.F., and Davis, B.B. (2002). Metabolism of N-acetylbenzidine and initiation of bladder cancer. Mutat. Res. 506/507:29-40.