257
Views
15
CrossRef citations to date
0
Altmetric
Research Article

Dephenylation of the Rubber Chemical N-Phenyl-2-Naphthylamine to Carcinogenic 2-Naphthylamine: A Classical Problem Revisited

, &
Pages 553-566 | Published online: 10 Oct 2008

REFERENCES

  • American Conference of Governmental Industrial Hygienists. N-Phenyl-beta-naphthylamine: TLV® Chemical Substances 7th Edition Documentation. American Conference of Governmental Industrial Hygienists, Cincinnati, OH, 2001, ACGIH Publication 7DOC-453
  • Anderson M. M., Mitchum R. K., Beland F. A. Hepatic microsomal metabolism and macromolecular binding of the antioxidant, N-phenyl-2-naphthylamine. Xenobiotica 1982; 12: 31–43
  • Anderson D., Styles J. A. The bacterial mutation test. Six tests for carcinogenicity. Br. J. Cancer 1978; 37(6)924–30
  • Anderson B. E., Zeiger E., Shelby M. D., Resnick M. A., Gulati D. K., Ivett J. L., Loveday K. S. Chromosome aberration and sister chromatid exchange test results with 42 chemicals. Environ. Mol. Mutagen. 1990; 16: 55–137, (Suppl. 18)
  • Bartsch H., Malaveille C., Camus A. M., Martel-Planche G., Brun G., Hautefeuille A., Sabadie N., Barbin A., Kuroki T., Drevon C., Piccoli C., Montesano R. 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. 1980; 76(1)1–50
  • Batten B. L., Hathway D. E. Dephenylation of N-phenyl-2-naphthylamine in dogs and its possible oncogenic implications. Br. J. Cancer 1977; 35: 342–346
  • Bolt H. M. The carcinogenic risk of ethene (ethylene). Toxicol Pathol. 1998; 26(3)454–456
  • Bolt H. M., Filser J. G. Olefinic hydrocarbons. A first risk estimate for ethene. Toxicol. Pathol. 1984; 12: 101–105
  • Bolt H. M., Filser J. G. Kinetics and disposition in toxicology. Example: carcinogenic risk estimate for ethylene. Arch. Toxicol. 1987; 60: 73–76
  • Bonser G. M., Clayson D. B., Jull J. W. An experimental inquiry into the cause of industrial bladder cancer. Lancet 1951; I(6677)286–288
  • Bonser G. M., Clayson D. B., Jull J. W., Pyrah L. N. The carcinogenic properties of 2-amino-1-naphthol hydrochloride and its parent amine 2-naphthylamine. Br. J. Cancer 1952; 6: 412–424
  • Booth J., Boyland E., Manson D. Metabolism of polycyclic compounds. 9. Metabolism of 2-naphthylamine in rat tissue slices. Biochem J. 1955; 60(1)62–71
  • Boyd J. A., Eling T. E. Prostaglandin H synthase-catalyzed metabolism and DNA binding of 2-naphthylamine. Cancer Res. 1987; 47(15)4007–4014
  • Boyland E., Manson D. The biochemistry of aromatic amines. Biochem. J. 1966a; 99: 189–199
  • Boyland E., Manson D. The biochemistry of aromatic amines. The metabolism of 2-naphthylamine and 2-naphthylhydroxylamine derivatives. Biochem. J. 1966b; 101: 84–102
  • Boyland E., Dukes C. E., Grover P. I. Carcinogenicity of 2-naphthylhydroxylamine and 2-naphthylamine. Br. J. Cancer 1963; 17: 79–84
  • Brill E. The role of dog bladder mucosa in the N-oxidation of arylamines. Res. Commun. Chem. Pathol. Pharmacol. 1977; 16(1)73–84
  • Brill E., Radomski J. L. Studies on the N-hydroxylation and the photochemical oxidation of 2-naphthylamine. Bladder Cancer, a Symposium. Aesculapius, Birmingham, AL 1967; 90–97
  • Case R. A., Hosker M. E. Tumour of the urinary bladder as an occupational disease in the rubber industry in England and Wales. Br. J. Prev. Soc. Med. 1954; 8: 9–50
  • Centers for Disease Control. Centers for Disease Control, Atlanta, GA 1976, Current Intelligence Bulletin 16. December 17
  • Conzelman G. M., Moulton J. E. Dose-response relationships of the bladder tumorigen 2-naphthylamine: A study in Beagle dogs. J. Natl. Cancer Inst. 1972; 49: 193–205
  • Degen G. H., Schlattjan J. H., Mähler S., Föllmann W., Golka K. Comparative metabolic activation of benzidine and N-acetylbenzidine by prostaglandin H synthase. Toxicol. Lett. 2004; 151: 135–142
  • Deichmann W. B., Radomski J. L. Carcinogenicity and metabolism of aromatic amines in the dog. J. Natl. Cancer Inst. 1969; 43(1)263–269
  • Deutsche Forschungsgemeinschaft. Phenyl-2-naphthylamin. Toxikologisch-arbeitsmedizinische Begründungen von MAK-Werten, D Henschler. VCH Verlag, Weinheim 1977; 1–6
  • Druckrey H., Küpfmüller K. Quantitative Analyse der Krebsentstehung. Z. Naturforsch. 1948; 3: 254
  • Föllmann W., Mähler S., Schuhmacher U. S., Guhe C. An in vitro model of the urinary bladder: cultured porcine urinary bladder epithelial cells. Toxicol. In Vitro 1997; 11: 427–433
  • Gehrmann G. H., Foulger J. H., Fleming A. J. Occupational carcinoma of the bladder. Proceedings of the 9th ICOH Congress, London, Section D, Session VIII. 1949; 472–475, http://www.cdldevoto.it/libraryavailablethrough accessed April 18, 2007
  • Golka K., Wiese A., Assenato G., Bolt H. M. Occupational exposure and urological cancer. World J. Urol. 2004; 21: 282–291
  • Gorrod L. W., Manson D. The metabolism of aromatic amines. Xenobiotica 1986; 16: 933–955
  • Green U., Holste J., Spikermann A. R. A comparative study of the chronic effects of magenta, paramagenta, and phenyl-beta-naphthylamine in Syrian golden hamsters. J. Cancer Res. Clin. Oncol. 1979; 95: 51–55
  • Green M. D., Tephly T. R. N-glucuronidation of carcinogenic aromatic amines catalyzed by rat hepatic microsomal preparations and purified rat liver uridine 5′-diphosphate-glucuronosyltransferases. Cancer Res. 1987; 47(8)2028–2031
  • Guhe C., Degen G. H., Schuhmacher U. S., Kiefer F., Föllmann W. Drug metabolizing enzyme activities in porcine urinary bladder epithelial cell cultures (PUBEC). Arch. Toxicol. 1996; 70: 599–606
  • Hamm T. E., Guest D., Dent J. G. Chronic toxicity and oncogenicity bioassay of inhaled ethylene in Fischer-344 rats. Fundam. Appl. Toxicol. 1984; 4: 473–478
  • Hammons G. J., Guengerich F. P., Weis C. C., Beland F. A., Kadlubar F. F. Metabolic oxidation of carcinogenic arylamines by rat, dog, and human hepatic microsomes and by purified flavin-containing and cytochrome P-450 monooxygenases. Cancer Res. 1985; 45(8)3578–3585
  • HVBG. Gefahrstoffliste 2006. 2006, BGIA Report 1/2006. Hauptverband der gewerblichen Berufsgenossenschaften, Sankt Augustin, Germany. ISBN 3-88383-700-8
  • IARC. 2-Naphthylamine. IARC Monogr Eval Carcinog Risk Hum. 1974; 4: 97–111
  • IARC. N-Phenyl-2-naphthylamine. IARC Monogr Eval Carcinog Risk Hum. 1978; 16: 325–341
  • IARC. N-Phenyl-2-naphthylamine. IARC Monogr Eval Carcinogen. Risk Hum. 1987; 318, Suppl. 7
  • IARC. Ethylene oxide. IARC Monogr. Eval. Carcinogen. Risk Hum. 1994; 60: 73–159
  • 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., Peters J. Bioassay of pesticides and industrial chemicals for tumorigenicity in mice: A preliminary note. J. Natl. Cancer Inst. 1969; 42(6)1101–1114
  • Kadlubar F. F., Miller J. A., Miller E. C. Hepatic microsomal N-glucuronidation and nucleic acid binding of N-hydroxy arylamines in relation to urinary bladder carcinogenesis. Cancer Res. 1977; 37(3)805–814
  • Kawachi T., Yahagi T., Kada T., Tazima Y., Ishidate M., Sasaki M., Sugiyama T. Cooperative programme on short-term assays for carcinogenicity in Japan. IARC Sci. Publ. 1980; 27: 323–330
  • Ketkar B., Mohr U. The chronic effects of magenta, paramagenta and phenyl-β-naphthylamine in rats after intragastric administration. Cancer Lett. 1982; 16: 203–206
  • Korallus U. Tumoren der Harnwege bei Beschäftigten in der deutschen Gummi-Industrie—Ein arbeitsmedizinisches Altlastenproblem. Zbl. Arbeitsmed. 1998; 48: 266–274
  • Kummer R., Tordoir W. F. Phenyl-betanaphthylamine (PBNA), another carcinogenic agent?. T. Soc. Geneesk. 1975; 53: 415–419
  • Laham S., Potvin M. Biological conversion of N-phenyl-2-naphthylamine to 2-naphthylamine in the Sprague-Dawley rat. Drug Chem. Toxicol. 1983; 6: 295–309
  • Laham S., Potvin M. Comparative N-dephenylation of N-phenyl-2-naphthylamine in Sprague-Dawley rats and New Zealand white rabbits. Chemosphere 1984; 13(5–6)657–667
  • Lakshimi V. M., Zenser T. V., Davis B. B. N′-(3′-Monophosphato-deoxyguanosin-8-yl)-N-acetylbenzidine formation by peroxidative metabolism. Carcinogenesis 1998; 19: 911–917
  • Lewalter J., Gries W. Haemoglobin adducts of aromatic amines Deutsche Forschungsgemeinschaft. Analysis of Hazardous Substances in Biological Materials, J Angerer, K H Schaller. Wiley-VCH. 2001; Vol. 7: 191–219
  • Lueersen L., Wellner T., Angerer J., Drexler H., Korinth G. 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, 2005, http://www.cdc.gov/niosh/topics/skin/OEESC2/AbPost048Lueersen.html[Abstract: accessed April 18, 2007]
  • Moore R. M., Woolf B. S., Stein H. P., Thomas A. W., Finklea J. F. Metabolic precursors of a known human carcinogen. Science 1977; 195: 344
  • Munn A. Bladder cancer and carcinogenic impurities in rubber additives. Rubber Ind. 1974; 8: 19–21
  • Norpoth K., Woitowitz H. J. Beruflich verursachte Tumoren. Grundlagen zur Entscheidung zur BK-Verdachtsanzeige. Deutscher Ärzteverlag, KölnGermany 1991
  • NTP. 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. 1988; 333: 1–168
  • Pliss G. B. Experimental study of ortho-toluidine carcinogenicity. Vopr Onkol. 2004; 50: 567–71, [Russian]
  • Pliss G. B., Zabezhinskii M. A. Carcinogenic risk of Neozone D (N-phenyl-2-naphthylamine). Vopr. Onkol. 1983; 29(7)91–3, [Russian]
  • Pliss G. B., Vlasov N. N., Zabezhinskii M. A. The carcinogenic and anticarcinogenic properties of neozon D. Vopr Onkol 1991; 37: 60–64, [Russian]
  • Poupko J. M., Hearn W. L., Radomski J. L. N-Glucuronidation of N-hydroxy aromatic amines: A mechanism for their transport and bladder-specific carcinogenicity. Toxicol. Appl. Pharmacol. 1979; 50(3)479–484
  • Rannug A., Rannug U., Ramel C. Genotoxic effects of additives in synthetic elastomers with special consideration to the mechanism of action of thiurams and dithiocarbamates. Prog. Clin. Biol. Res. 1984; 141: 407–419
  • Ringe D., Turesky R. J., Skipper P. L., Tannenbaum S. R. Structure of the single stable hemoglobin adduct formed by 4-aminobiphenyl in vivo. Chem. Res Toxicol. 1988; 1(1)22–24
  • Schmidt E., Lohs K. H., Otto J. Industrietoxikologische Bewertung von Vulkanisationsdämpfen unter besonderer Berücksichtigung stickstoffhaltiger Alterungsschutzmittel. Z. Ges. Hyg. 1983; 28: 442–446
  • Scott T. S. Carcinogenic and chronic toxic hazards of aromatic amines. Elsevier, New York 1962
  • Skipper P. L., Tannenbaum S. R. Protein adducts in the molecular dosimetry of chemical carcinogens. Carcinogenesis 1990; 11(4)507–518
  • Sofuni T., Matsuoka A., Sawada M., Ishidate M., Jr., Zeiger E., Shelby M. D. A comparison of chromosome aberration induction by 25 compounds tested by two Chinese hamster cell (CHL and CHO) systems in culture. Mutat. Res. 1990; 241(2)175–213
  • Sorahan T., Hamilton L., Jackson J. R. 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. 2000; 57(2)106–115
  • Takemura N., Shimizu H. Mutagenicity of some aromatic amino and nitro compounds. Mutat. Res. 1978; 54(2)256–257
  • Tolbert P. E. Oils and cancer. Cancer Causes Control 1997; 8: 386–405
  • Troll W., Nelson N. N-Hydroxy-2-naphthylamine, a urinary metabolite of 2-naphthylamine in man and dog. Fed. Proc. 1961; 20: 41
  • Veys C. A. Bladder cancer in rubber workers, a PBNA exposed workforce. Progress in Rubber and Plastics Technology 1996; 12: 258–273
  • Walker V. E., Wu K. Y., Upton P. B., Ranasinghe A., Schelle N., Cho M. H., Vergnes J. S., Skopek T. R., Swenberg J. A. Biomarkers of exposure and effect as indicators of potential carcinogenic risk arising from in vivo metabolism of ethylene to ethylene oxide. Carcinogenesis 2000; 21(9)1661–1669
  • Wang H. W., Wang D., Dzeng R. W. Carcinogenicity of N-phenyl-1-naphthylamine and N-phenyl-2-naphthylamine in mice. Cancer Res. 1984a; 44: 3098–3100
  • Wang H. W., You Y. J., Qu Y. H., Wang Y. F., Wang D., Long Y. M., Ni J. A. Investigation of cancer epidemiology and study of carcinogenic agents in the Shanghai rubber industry. Cancer Res. 1984b; 44: 3101–3105
  • Wang J., DeMaio W., Chandrasekaran A., Shen L., Bach A. C., 2nd, Scatina J., Talaat R. Mechanism study of N-dephenylation mediated through a N-para-hydroxy metabolite. Curr. Drug Discov. Technol. 2006; 3(2)101–114
  • Weiss T. 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 2005, http://www.opus.ub.uni-erlangen.de/opus/volltexte/2005/273/pdf/[Available through: DissertationTobiasWeiss-21112005.pdf accessed April 18, 2007]
  • Zeiger E., Anderson B., Haworth S., Lawlor T., Mortelmans K. Salmonella mutagenicity tests: IV. Results from the testing of 300 chemicals. Environ Mol. Mutagen. 1988; 11: 1–157, (Suppl. 12)
  • Zenser T. V., Lakshimi V. M., Hsu F. F., Davis B. B. Metabolism of N-acetylbenzidine and initiation of bladder cancer. Mutat. Res. 2002; 506/507: 29–40

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.