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Research Article

Biomonitoring of arylamines and nitroarenes

Gabriele Sabbioni Walther-Straub-Institut für Pharmakologie und Toxikologie, Ludwig-Maximilians-Universität München, Nussbaumstrasse 26, D-80336 München, Germany
&
Christopher R. Jones Walther-Straub-Institut für Pharmakologie und Toxikologie, Ludwig-Maximilians-Universität München, Nussbaumstrasse 26, D-80336 München, Germany
Pages 347-421 | Published online: 29 Sep 2008

  • AHLBORG, G. JR, EINISTO, P. and SORSA, M. 1988, Mutagenic activity and metabolites in the urine of workers exposed to trinitrotoluene (TNT). British Journal of Industrial Medicine, 45, 353-358.
  • AL-ATRASH, J., ZHANG, Y. J., LIN, D., KADLUBAR, F. F. and SANTBLLA, R. M. 1995, Quantitative immunohistochemical analysis of 4-aminobiphenyl-DNA in cultured cells and mice: comparison to gas chromatography/mass spectroscopy analysis. Chemical Research in Toxicology, 8, 747-752.
  • ALBERTINI, R. J., ANDERSON, D., DOUGLAS, G. R., HAGMAR, L., HEMMINKI, K., MKRLO, F., NATARAJAN, A. T., NORPPA, H., SHUKER, D. E. G., TICE, R., WATERS, M. D. and AITIO, A. 2000, IPCS guidelines for the monitoring of genotoxic effects of carcinogens in humans. Mutation Research, 463, 111-172.
  • ALBRECHT, W. 1985, Untersuchungen zur Hämoglobinbindung aromatischer Amino- und Nitroverbindungen bei Ratten. PhD thesis, University of Würzburg, Germany.
  • ALBRECHT, W. and NEUMANN, H.G. 1985, Biomonitoring of aniline and nitrobenzene. Hb binding in rats and analysis of adducts. Archives of Toxicology, 57, 1-5.
  • ANDERSON, K. E., HAMMONS, G. J., KADLUBAR, F. F., POTTER, J. D., KADERLIK, K. R., ILEIT, K. F., MINCHIN, R. F., TEITEL, C. H., CHOU, H.C., MARTIN, M. V., GUENGERICH, F. P., BARONE, G. W., LANG, N. P. and PETERSON, L. A. 1997, Metabolic activation of aromatic amines by human pancreas. Carcinogenesis, 18, 1085-1092.
  • ANDRES, H. H., VOGEL, R. S., TARR, G. E., JOHNSON, L. and WEBER, W. W. 1987, Purification, physicochemical, and kinetic properties of liver acetyl-CoA: arylamine N-acetyltransferase from rapid acetylator rabbits. Molecular Pharmacology, 31, 446-456.
  • ANGERER, J. and KAERLEIN, H. U. 1997, Gas Chromatographie method using electron-capture detection for the determination of musk xylene in human blood samples. Biological monitoring of the general population. Journal of Chromatography B, 693, 71-78.
  • ANGERER, J. and WEISMANTEL, A. 1998, Biological monitoring of dinitrotoluene by gas chromatographicmass spectrometric analysis of 2,4-dinitrobenzoic acid in human urine. Journal of Chromatography B, 713, 313-322.
  • ASHBY, J. and PATON, D. 1993, The influence of chemical structure on the extent and sites of carcinogenesis for 522 rodent carcinogens and 55 different human carcinogen exposures. Mutation Research, 286, 3-74.
  • ASHBY, J. and TENNANT, R. W. 1991, Definitive relationships among chemical structure, carcinogenicity and mutagenicity for 301 chemicals tested by the US NTP. Mutation Research, 257, 229-306.
  • ASHBY, J., PATON, D., LEFEVRE, P. A., STYLES, J. A. and ROSE, F. L. 1982, Evaluation of two suggested methods of deactivating organic carcinogens by molecular modification. Carcinogenesis, 3, 1277-1282.
  • BABU, S. R., LAKSHMI, V. M., HUANG, G. P., ZENSER, T. V. and DAVIS, B. B. 1996, Glucuronide conjugates of 4-ABP and its N-hydroxy metabolites. pH stability and synthesis by human and dog liver. Biochemical Pharmacology, 51, 1679-1685.
  • BADAWI, A. F., HIRVONEN, A., BELL, D. A., LAND, N. P. and KADLUBAR, F. F. 1995, Role of aromatic amine acetyltransferases, NAT1 and NAT2, in carcinogen-DNA adduct formation in the human urinary bladder. Cancer Research, 55, 5230-5237.
  • BADAWI, A. F., STERN, S. J., LANG, N. P. and KADLUBAR, F. F. 1996, Cytochrome P-450 and acetyltransferase expression as biomarkers of carcinogen-DNA adduct levels and human cancer susceptibility. Progress in Clinical Biological Research, 395, 109-140.
  • BADER, M., GOEN, T., MULLER, J. and ANGERER, J. 1998, Analysis of nitroaromatic compounds in urine by gas chromatography-mass spectrometry for the biological monitoring of explosives. Journal of Chromatography B, 710, 91-99.
  • BAILEY, E., BROOKS, A. G., BIRD, I., FARMER, P. B. and STREET, B. 1990, Monitoring exposure to methylenedianiline by the gas chromatography-mass spectrometry determination of adducts to hemoglobin. Analytical Biochemistry, 190, 175-181.
  • BAILEY, E., BROOKS, A. G., FARMER, P. B. and STREET, B. 1993, Monitoring exposure to 4,4'-methylenebis(2-chloroaniline) through the gas chromatography-mass spectrometry measurement of adducts to hemoglobin. Environmental Health Perspectives, 99, 175-177.
  • BALL, L. M., KOHAN, M. J., INMON, J. P., CLAXTON, L. D. and LEWTAS, J. 1984, Metabolism of 1-nitro [14 C]pyrene in vivo in the rat and mutagenicity of urinary metabolites. Carcinogenesis, 5, 1557-1564.
  • BARTSCH, H. 2000, Studies on biomarkers in cancer etiology and prevention: a summary and challenge of 20 years of interdisciplinary research. Mutation Research, 462, 255-279.
  • BARTSCH, H., CAPORASO, N., CODA, M., KADLUBAR, F., MALAVEILLE, C., SKIPPER, P., TALASKA, G., TANNENBAUM, S. R. and VINEIS, P. 1990, Carcinogen hemoglobin adducts, urinary mutagenicity, and metabolic phenotype in active and passive cigarette smokers. Journal of the National Cancer Institute, 82, 1826-1831.
  • BEACH, A. C. and GUPTA, R. C. 1992, Human biomonitoring and the 32P-postlabeling assay. Carcinogenesis, 13, 1053-1074.
  • BEAUCHAMP, R. O. JR, IRONS, R. D., RICKERT, D. E., COUCH, D. B. and HAMM, T. E. JR. 1982, A critical review of the literature on nitrobenzene toxicity. Critical Reviews in Toxicology, 11, 33-84.
  • BELAND, F. A. and KADLUBAR, F. F. 1985, Formation and persistence of arylamine adducts in vivo. Environmental Health Perspectives, 62, 19-30.
  • BELAND, F. A. and KADLUBAR, F. F. 1990, Metabolic activation and DNA adducts of aromatic amines and nitroaromatic hydrocarbons. In Chemical Carcinogenesis and Mutagenesis I, Vol. 1, edited by C. S. Cooper (Berlin: Springer), pp. 267-325.
  • BEUNU, F. A., TULLIS, D. L., KADLUBAR, F. F., STRAUB, K. M. and EVANS, F. E. 1980, Characterization of DNA adducts of the carcinogen N-methyl-4-aminoazobenzene in vitro and in vivo. Chemico-Biological Interactions, 31, 1-17.
  • BELAND, F. A., BERANEK, D. T., DOOLEY, K. L., HEFLICH, R. H. and KADLUBAR, F. F. 1983, Arylamine-DNA adducts in vitro and in vivo: their role in bacterial mutagenesis and urinary bladder carcinogenesis. Environmental Health Perspectives, 49, 125-134.
  • BELAND, F. A., DOERGE, D. R., CHURCHWELL, M. I., POIRIER, M. C., SCHOKET, B. and MARQUES, M. M. 1999, Synthesis, characterization, and quantitation of a 4-aminobiphenyl-DNA adduct standard. Chemical Research in Toxicology, 12, 68-77.
  • BENIGNI, R., ANDREOLI, C. and GIULIANI, A. 1994, QSAR models for both mutagenic potency and activity: application to nitroarenes and aromatic amines. Environmental Molecular Mutagenesis, 24, 208-219.
  • BENIGNI, R., GIULIANI, A., FRANKE, R. and GRUSKA, A. 2000, Quantitative structure-activity relationships of mutagenic and carcinogenic aromatic amines. Chemical Review, 100, 3697-3714.
  • BESARATI, N. A., VAN STRAATEN, H. W., KLEINJANS, J. C. and VAN SCHOOTEN, F. J. 2000, Immunoperoxidase detection of 4-aminobiphenyl and polycyclic aromatic hydrocarbons-DNA adducts in induced sputum of smokers and non-smokers. Mutation Research, 468, 125-135.
  • BEYERBACH, A. and SABBIONI, G. 1999, Biomonitoring of arylamines: haemoglobin adducts of aniline derivatives. Biomarkers, 4, 229-236.
  • BEYERBACH, A., FARMER, P. B. and SABBONI, G. 1996, Synthesis and analysis of DNA adducts of arylamines. Biomarkers, 1, 9-20.
  • BIAGLOW, J. E., JACOBSEN, B., GREENSTOCK, C. L. and RALEIGH, J. 1977, Effect of nitrobenzene derivatives on electron transfer in cellular and chemical models. Molecular Pharmacology, 13, 269-282.
  • BIRNER, G. and NEUMANN, H. G. 1988, Biomonitoring of aromatic amines II: Hemoglobin binding of some monocyclic aromatic amines. Archives of Toxicology, 62, 110-115.
  • BIRNER, G., ALBRECHT, W. and NEUMANN, H. G. 1990, Biomonitoring of aromatic amines. Ill: Hemoglobin binding of benzidine and benzidine congeners. Archives of Toxicology, 64, 97-102.
  • BOOGAARD, P. J., FOKKEMA, G. N., BEULINK, G. D., BOUSKILL, J. and VAN SITTERT, N. J. 1994a, Molecular dosimetry of 2,4-difluoroaniline in humans and rats by determination of hemoglobin adducts. Environmental Health Perspectives, 102, Supplement 6, 27-29.
  • BOOGAARD, P. J., BEULINK, G. D. and VAN SITTERT, N. J. 1994b, Biological monitoring of exposure to 3-chloro-4-fluoroaniline by determination of a urinary metabolite and a hemoglobin adduct. Environmental Health Perspectives, 102, Supplement 6, 23-25.
  • BRANCO, P. S., ANTUNES, A. M. M., MARQUES, M. M., CHIARELLI, M. P., LOBO, A. M. and PRABHAKAR, S. 1999, New syntheses of DNA adducts from methylated anilines present in tobacco smoke. Chemical Research in Toxicology, 12, 1223-1233.
  • BROWN, K. K., TEASS, A. W., SIMON, S. and WARD, E. M. 1995, A biological monitoring method for o-toluidine and aniline in urine using high performance liquid chromatography with electrochemical detection. Applied Occupational and Environmental Hygiene, 10, 557-565.
  • BRYANT, M. S., SKIPPER, P. L., TANNENBAUM, S. R. and MACLURE, M. 1987, Hemoglobin adducts of 4-aminobiphenyl in smokers and nonsmokers. Cancer Research, 47, 602-608.
  • 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. Proceedings of the National Academy of Sciences of the USA, 85, 9788-9791.
  • BRYANT, M. S., SKIPPER, P. L., WISHNOK, J. S., STILLWELL, W. G., GLOGOWSKI, J. A. and TANNENBAUM, S. R. 1993, Determination of hemoglobin adducts of aromatic amines by gas chromatography-mass spectrometry. In Environmental Carcinogens, Methods of Analysis, and Exposure Measurement, IARC Scientific Publications No. 109, Vol. 12, edited by B. Seifert, H. J. van de Wiel, B. Dodet and I. K. O'Neill (Lyon: International Agency for Research on Cancer), pp. 281-292.
  • BRYANT, M. S., SIMMONS, H. F., HARRELL, R. E. and HINSON, J. A. 1994, 2,6-Dimethylaniline-hemoglobin adducts from lidocaine in humans. Carcinogenesis, 15, 2287-2290.
  • CARTWRIGHT, R. A., ROGERS, H. J., BARHAM-HALL, D., GLASHAHN, R. W., AHMAD, R. A., HIGGINS, E. and KAHN, M. A. (1982) Role of N-acetyltransferase phenotypes in bladder carcinogenesis: a pharmacogenetic approach to bladder cancer. Lancet, 2, 842-845.
  • CASE, R. A. M., HOSKER, M. E. and MCDONALD, D. B. 1954, Tumors of urinary bladder in workmen engaged in the manufacture and use of certain dyestuff intermediates in the British chemical industry. Part 1. The role of aniline, benzidine, alpha-naphthylamine and beta-naphthylamine. British Journal of Industrial Medicine, 11, 75-104.
  • CASHMAN, J. R. 1995, Structural and catalytic properties of the mammalian flavin-containing monooxygenase. Chemical Research in Toxicology, 8, 165-181.
  • 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. Journal of the National Cancer Institute, 93, 538-545.
  • CHAN, S. C., BIRDSELL, D. C. and GRADEEN, C. Y. 1991, Detection of toluenediamines in the urine of a patient with polyurethane-covered breast implants. Clinical Chemistry, 37, 756-758.
  • CHEEVER, K. L., RICHARDS, D. E., WEIGEL, W. W., BEGLEY, K. B., DEBORD, D. G., SWEARENGIN, T. F. and SAVAGE, R. E. JR. 1990, 4,4'-Methylene-bis(2-chloroaniline) (MOCA): comparison of macromolecular adduct formation after oral or dermal administration in the rat. Fundamental and Applied Toxicology, 14, 273-283.
  • CHEEVER, K. L., DEBORD, D. G. and SWEARENGIN, T. F. 1991, 4,4'-Methylenebis(2-chloroaniline) (MOCA): the effect of multiple oral administration, route, and phenobarbital induction on macromolecular adduct formation in the rat. Fundamental and Applied Toxicology, 16, 71-80.
  • CHEEVER, K. L., DEBORD, D. G., SWEARENGIN, T. F. and BOOTH-JONES, A. D. 1992, Ortho-toluidine blood protein adducts: HPLC analysis with fluorescence detection after a single dose in the adult male rat. Fundamental and Applied Toxicology, 18, 522-531.
  • CHIANG, T.-A., PEI-FEN, W., YING, L. S., WANG, L. F. and KO, Y. C. 1999, Mutagenicity and aromatic amine content of fumes from heated cooking oils produced in Taiwan. Food and Chemical Toxicology, 37, 125-134.
  • CHISM, J. P. and RICKERT, D. E. 1991, Isomer- and sex-specific bioactivation of mononitrotoluenes. Role of enterohepatic circulation. Drug Metabolism and Disposition, 13, 651-657.
  • CHO, B. P., BELAND, F. A. and MARQUES, M. M. 1992, NMR structural studies of a 15-mer DNA sequence from a ras protooncogene, modified at the first base of codon 61 with the carcinogen 4-aminobiphenyl. Biochemistry, 31, 9587-9602.
  • CHO, B. P., BELAND, F. A. and MARQUES, M. M. 1994, NMR structural studies of a 15-mer DNA duplex from a ras protooncogene modified with the carcinogen 2-aminofluorene: conformational heterogeneity. Biochemistry, 33, 1373-1384.
  • CHUNG, K.-T., KIRKOVSKY, L., KIRKOVSKY, A. and PURCELL, W. P. 1997, Review of mutagenicity of monocyclic aromatic amines: quantitative structure-activity relationships. Mutation Research, 387, 1-16.
  • CLAPP, D. E., PIACITELLI, G. M. ZAEBST, D. D. and WARD, E. 1991, Assessing exposure to 4,4'- methylene-bis-(2-chloroaniline) (MBOCA) in the workplace. Applied Occupational and Environmental Hygiene, 6, 125-130.
  • COCKER, J., BROWN, L. C., WILSON, H. K. and ROLLINS, K. 1988a, A GC/MS method for the determination of 4,4'-diaminodipheny lmethane and substituted analogues in urine. Journal of Analytical Toxicology, 12, 9-14.
  • COCKER, J., BOOBIS, A. R. and DAVIES, D. S. 1988b, Determination of the N-acetyl metabolites of 4,4'-methylene dianiline and 4,4'-methylene-bis(2-chloroaniline) in urine. Biomedical and Environmental Mass Spectrometry, 17, 161-167.
  • COCKER, J., BOOBIS, A. R., WILSON, H. K. and GOMPERTZ, D. 1990, Evidence that a beta-N-glucuronide of 4,4'-methylenebis(2-chloroaniline) (MbOCA) is a major urinary metabolite in man: implications for biological monitoring. British Journal of Industrial Medicine, 47, 154-161.
  • COCKER, J., NUTLEY, B. P. and WILSON, H. K. 1994, A biological monitoring assessment of exposure to methylene dianiline in manufacturers and users. Occupational and Environmental Medicine, 51, 519-522.
  • COCKER, J., NUTLEY, B. P. and WILSON, H. K. 1996, Methylenebis(2-chloroaniline) (MbOCA): towards a biological monitoring guidance value. Biomarkers, 1, 185-189.
  • 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 exposed to the tobacco smoke carcinogen in utero. Journal of the National Cancer Institute, 83, 274-280.
  • CULP, S. J., POIRIER, M. C. and BELAND, F. A. 1993, Biphasic removal of DNA adducts in a repetitive DNA sequence after dietary administration of 2-acetylaminofluorene. Environmental Health Perspectives, 99, 273-275.
  • CULP, S. J., ROBERTS, D. W., TALASKA, G., LANG, N. P., FU, P. P., LAY, J. O. JR, TEITEL, C. H., SNAWDER, J. E., VON TUNGELN, L. S. and KADLUBAR, F. F. 1997, 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, 378, 97-112.
  • 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 Tl bladder cancer of smokers and nonsmokers. Carcinogenesis, 17, 911-916.
  • DALENE, M., JACOBSSON, K., RANNUG, A., SKARPING, G. and HAGMAR, L. 1996, MDA in plasma as a biomarker of exposure to pyrolysed MDI based polyurethane; correlations with estimated cumulative dose and genotype for N-acetylation. International Archives of Occupational and Environmental Health, 68, 165-169.
  • DALLINGA, J. W., PACHEN, D. M. F. A., WIJNHOVEN, S. W. P., BREEDIJK, A., VANTVEER, L., WIGBOUT, G., VANZANDWIJK, N., MAAS, L. M., VANAGEN, E., KLEINJANS, J. C. S. and VAN SCHOOTEN, F. J. 1998, The use of 4-aminobiphenyl hemoglobin adducts and aromatic DNA adducts in lymphocytes of smokers as biomarkers of exposure. Cancer Epidemiology, Biomarkers and Prevention, 7, 571-577.
  • DEBIEC-RYCHTER, M., LAND, S. J. and KING, C. M. 1999, Histological localization of acetyltransferases in human tissue. Cancer Letters, 143, 99-102.
  • DEBNATH, A. K., DEBNATH, G., SHUSTERMAN, A. J. and HANSCH, C. 1992a, A QSAR investigation of the role of hydrophobicity in regulating mutagenicity in the Ames test: 1. Mutagenicity of aromatic and heteroaromatic amines in Salmonella typhimurium TA98 and TA100. Environmental Molecular Mutagenesis, 19, 37-52.
  • DEBNATH, A. K., LOPEZ DE COMPADRE, R. L., SHUSTERMAN, A. J. and HANSCH, C. 1992b, Quantitative structure-activity relationship investigation of the role of hydrophobicity in regulating mutagenicity in the Ames test: 2. Mutagenicity of aromatic and heteroaromatic nitro compounds in Salmonella typhimurium TA100. Environmental Molecular Mutagenesis, 19, 53-70.
  • DEBORD, D. G., SWEARENGIN, T. F., CHEEVER, K. L., BOOTH-JONES, A. D. and WISSINGER, L. A. 1992, Binding characteristics of ortho-toluidine to rat hemoglobin and albumin. Archives of Toxicology, 66, 231-236.
  • DEBRUIN, L. S., JOSEPHY, P. D. and PAWLISZYN, J. B. 1998, Solid-phase microextraction of monocyclic aromatic amines from biological fluids. Analytical Chemistry, 70, 1986-1992.
  • DEBRUIN, L. S., PAWLISZYN, J. B. and JOSEPHY, P. D. 1999, Detection of monocyclic aromatic amines, possible mammary carcinogens, in human milk. Chemical Research in Toxicology, 12, 78-82.
  • DELCLOS, K. B. and KADLUBAR, F. F. 1997, Carcinogenic aromatic amines and amides. In Comprehensive Toxicology. Vol. 12, Chemical carcinogens and anticarcinogens, edited by G. T. Bowden and S. M. Fischer (New York: Eisevier Science), pp. 141-170.
  • DELCLOS, K. B., MILLER, W. G. and MILLER, J. A. 1984, Aminoazobenzene and N,N-dimethyl-4-aminoazobenzene as equipotent hepatic carcinogens in male C57BL/6 x C3H/He mice and characterization of N-(deoxyguanosin-8-yl)-4-aminoazobenzene as the major persistent hepatic DNA-bound dye in these mice. Cancer Research, 44, 2540-2550.
  • DEL SANTO, P., MONETI, G., SALVADORI, M., SALTUITI, C., DELLE ROSE, A. and DOLARA, P. 1991, Levels of the adducts of 4-aminobiphenyl to hemoglobin in control subjects and bladder carcinoma patients. Cancer Letters, 60, 245-251.
  • DEMARINI, D. M., BROOKS, L. R., BHATNAGAR, V. K., HAYES, R. B., EISCHEN, B. T., SHELTON, M. L., ZENSER, T. V., TALASKA, G., KASHYAP, S. K., DOSEMECI, M., KASHYAP, R., PARIKH, D. J, LAKSHMI, V., HSU, F., DAVIS, B. B., JAEGER, M. and ROTHMAN, N. 1997, Urinary mutagenicity as a biomarker in workers exposed to benzidine: correlation with urinary metabolites and urothelial DNA adducts. Carcinogenesis, 18, 981-988.
  • DE RICCARDIS, F., BONALA, R. R. and JOHNSON, F. 1999, A general method for the synthesis of the N2-and N6- carcinogenic amine adducts of 2' -deoxyguanosine and 2' -deoxyadenosine. Journal of the American Chemical Society, 121, 10453-10460.
  • D'ERRICO, A., TAIOLI, E., CHEN, X. and VINEIS, P. 1996, Genetic metabolic polymorphisms and the risk of cancer: a review of the literature. Biomarkers, 1, 149-173.
  • D'ERRICO, A., MALATS, N., VINEIS, P. and BOFFETTA, P. 1999, Review of studies of selected metabolic polymorphisms and cancer. In Metabolic Polymorphisms and Susceptibility to Cancer, IARC Scientific Publications No. 148, edited by P. Vineis, N. Malats, M. Lang, A. d'Errico, N. Caporaso, J. Cuzick and P. Boffetta (Lyon: International Agency for Research on Cancer), pp. 323-393.
  • DIETER, H. H. (editor) 1994, Summenbetaertung von nitro (amino)aromatischen Verbindungen Kriterien und Konzentrationsvorschläge zur gesundheitlichen Bewertung von 35 Sprengstoff-typischen Verbindungen und Abbauprodukten in Baden und Trinlaaasser. WaBoLu Hefte 8/1994 (Berlin: Institut für Wasser-, Boden- und Lufthygiene des Bundesgesundheitsamtes) pp. 1-165.
  • DOERGE, D. R., CHURCHWELL, M. L, MARQUES, M. M. and BELAND, F. A. 1999, Quantitative analysis of 4-aminobiphenyl-C8-deoxyguanosyl DNA adducts produced in vitro and in vivo using HPLC-ES-MS. Carcinogenesis, 20, 1055-1061.
  • DOOLEY, K. L., BElAND, F. A., BUCCI, T. J. and KADLUBAR, F. F. 1984, Local carcinogenicity, rates of absorption, extent and persistence of macromolecular binding, and acute histopathological effects of N-hydroxy-1-naphthylamine and N-hydroxy-2-naphthylamine. Cancer Research, 44, 1172-1177.
  • EHRENBERG, L., HIESCHE, K. D., OSTERMAN-GOLKAR, S. and WEINBERG, I. 1974, Evaluation of genetic risks of alkylating agents: tissue doses in the mouse from air contaminated with ethylaene oxide. Mutation Research, 24, 83-103.
  • EL-BAYOUMY, K., DONAHUE, J. M., HECHT, S. S. and HOMANN, D. 1986, Identification and quantitative determination of aniline and toluidines in human urine. Cancer Research, 46, 6064-6067.
  • EVER, P. 1979, Reactions of nitrosobenzene with reduced glutathione. Chemico-Biological Interactions, 24, 227-239.
  • EVER, P. and GALLEMANN, D. 1996, Reactions of nitrosoarenes with SH groups. In The Chemistry of Amino, Nitroso, Nitro and Related Groups, Supplement F2, edited by S. Patai (New York: John Wiley & Sons), pp. 999-1039.
  • EVER, P., LIERHEIMER, E. and STROSAR, M. 1983, Site and mechanism of covalent binding of 4-dimethylaminophenol to human hemoglobin, and its implications to the functional properties. Molecular Pharmacology, 23, 282-290.
  • FAGAN, J. M. and WAXMAN, L. 1991, Purification of a protease in red blood cells that degrades oxidatively damaged hemoglobin. Biochemical Journal, 277, 779-786.
  • FELTES, J., LEVSEN, K., VOLMER, D. and SPIEKERMANN, M. 1990, Gas Chromatographie and mass spectrometric determination of nitroaromatics in water. Journal of Chromatography, 518, 21-40.
  • FENG, Y., RUSTAN, T. D., FERGUSON, R. J., DOLL, M. A. and HEIN, D. W. 1994, Acetylator genotype-dependent formation of 2-aminofluorene-hemoglobin adducts in rapid and slow acetylator Syrian hamsters congenic at NAT2 locus. Toxicology and Applied Pharmacology, 124, 10-15.
  • FIAMMANG, T. J., YEROKUN, T., BRYANT, M. S., COUCH, L. H., KIRLIN, W. G., LEE, K. J., OGOLLA, F., FERGUSON, R. J., TALASKA, G. and HEIN, D. W. 1992a, Hemoglobin adduct and hepatic- and urinary bladder-DNA adduct levels in rapid and slow acetylator Syrian inbred hamsters administered 2-aminofluorene. Journal of Pharmacology and Experimental Therapeutics, 260, 865-871.
  • FLAMMANG, T. J., COUCH, L. H., LEVY, G. N., WEBER, W. W. and WISE, C. K. 1992b, DNA adduct levels in congenic rapid and slow acetylator mouse strains following chronic administration of 4-aminobiphenyl. Carcinogenesis, 13, 1887-1891.
  • FREDERICK, C. B., WEIS, C. C., FLAMMANG, T. J., MARTIN, C. N. and KADLUBAR, F. F. 1985, Hepatic N-oxidation, acetyl-transfer and DNA-binding of the acetylated metabolites of the carcinogen, benzidine. Carcinogenesis, 6, 959-965.
  • FU, P. P. and HERRENO-SAENZ, D. 1999, Nitro-polycyclic aromatic hydrocarbons: a class of genotoxic environmental pollutants. Environmental Carcinogenesis and Ecotoxicology Reviews, C17, 1-43.
  • GARNER, R. C. 1998, The role of DNA adducts in chemical Carcinogenesis. Mutation Research, 402, 67-75.
  • GARNER, R. C., MARTIN, C. N. and CLAYSON, D. B. 1984, Carcinogenic aromatic amines and related compounds. In Chemical Carcinogens, ACS Monograph 182, edited by C. E. Searle (Washington, D C: American Chemical Society), pp. 175-276.
  • GAUGLER, B. J. M. and NEUMANN, H.-G. 1979, The binding of metabolites formed from aminostilbene derivatives to nucleic acids in the liver of rats. Chemico-Biological Interactions, 24, 355-372.
  • GAYLOR, D. W., KADLUBAR, F. F. and BELAND, F. A. 1992, Application of biomarkers to risk assessment. Environmental Health Perspectives, 98, 139-141.
  • GLATT, H. R. 2000, Sulfotransferases in the bioactivation of xenobiotics. Chemico-Biological Interactions, 129, 141-170.
  • GODSCHALK, R. W., DALLINGA, J. W., WIKMAN, H., RISCH, A., KLEINJANS, J. C., BARTSCH, H. and VAN SCHOOTEN, F. J. 2001, Modulation of DNA and protein adducts in smokers by genetic polymorphisms in GSTM1, GSTT1, NAT1 and NAT2. Pharmacogenetics, 11, 389-398.
  • GOLD, L. S., MANLEY, N. B., SLONE, T. H., GARNKEL, G. B., ROHRBACH, L. and AMES, B. N. 1993, The fifth plot of the carcinogenic potency database: results of animal bioassays published in the general literature through 1988 and by the National Toxicology Program through 1989. Environmental Health Perspectives, 100, 65-135.
  • GONCALVES, L. L., BELAND, F. A. and MARQUES, M. M. 2001, Synthesis, characterization, and comparative 32P-postlabeling efficiencies of 2,6-dimethylaniline-DNA adducts. Chemical Research in Toxicology, 14, 165-174.
  • GORROD, J. W. and MANSON, D. 1986, The metabolism of aromatic amines. Xenobiotica, 16, 933-955.
  • GOWIK, P., DIETER, H. H. and LITZ, N. 1994, Mess- und Vergleichsweise von Nitro-/Aminoaromaten und weiterer Sprengstoff-typischer Verbindungen im Boden, Sicker- und Grundwasser, WaBoLu Hefte 1/1994 (Berlin: Institut für Wasser-, Boden- und Lufthygiene des Bundesgesundheitsamtes), pp. 1-55.
  • GREEN, L. C., SKIPPER, P. L., TURESKY, R. J., BRYANT, M. S. and TANNENBAUM, S. R. 1984, In vivo dosimetry of 4-aminobiphenyl in rats via a cysteine adduct in hemoglobin. Cancer Research, 44, 4254-4259.
  • GU, Z., GORIN, A., KRISHNASAMY, R., HINGERTY, B. E., BASU, A. K., BROYDE, S. and PATEL, D. J. 1999, Solution structure of the N-(deoxyguanosin-8-yl)-1-aminopyrene ([APJdG) adduct opposite dA in a DNA duplex. Biochemistry, 38, 10843-10854.
  • GUENGBRICH, F. 2001, Common and uncommon cytochrome P450 reactions related to metabolism and chemical toxicity. Chemical Research in Toxicology, 14, 611-650.
  • GUPTA, R. C., EARLEY, K., FULLERTON, N. F. and BELAND, F. A. 1989, Formation and removal of DNA adducts in target and nontarget tissues of rats administered multiple doses of 2-acetylaminophenanthrene. Carcinogenesis, 10, 2025-2033.
  • HAACK, T., ERDINGER, L. and BOCHE, G. 2001, Mutagenicity in Salmonella typhimurium TA98 and TA100 of nitroso and respective hydroxylamine compounds. Mutation Research, 491, 183-193.
  • HAMMOND, S. K., COGHLIN, J., GANN, P. H., PAUL, M., TAGHIZADEH, K., SKIPPER, P. L. and TANNENBAUM, S. R. 1993, Relationship between environmental tobacco smoke exposure and carcinogen-hemoglobin adduct levels in nonsmokers. Journal of the National Cancer Institute, 85, 474-478. Comments in Journal of the National Cancer Institute, 85, 1693-1696.
  • HAMMONS, G. J., DOOLEY, K. L. and KADLUBAR, F. F. 1991, 4-Aminobiphenyl-hemoglobin adduct formation as an index of in vivo N-oxidation by hepatic cytochrome P-450IA2. Chemical Research in Toxicology, 4, 144-147.
  • HARTTER, D. R. 1985, The use and importance of nitroaromatic compounds in the chemical industry. In Toxicity of Nitroaromatic Compounds, edited by D. E. Rickert (Washington: Hemispher Publishing Cooperation), pp. 1-13.
  • HATFIELD, T. R., ROBERTS, E. C., BELL, I. F., CLUNIE, J. C., KALLA, P. J. and MCKAY, D. L. 1982, Urine monitoring of textile workers exposed to dichlorobenzidine-derived pigments. Journal of Occupational Medicine, 24, 656-658.
  • HAYES, R. B., BI, W., ROTHMAN, N., BROLY, F., CAPORASO, N., FENG, P., YOU, X., YIN, S., WOOSLEY, R. L. and MEYBR, U. A. 1993, N-Acetylation phenotype and genotype and risk of bladder cancer in benzidine-exposed workers. Carcinogenesis, 14, 675-678.
  • HIRVONEN, A. 1999, Polymorphic NATs and cancer predisposition. In Metabolic Polymorphisms and Susceptibility to Cancer, IARC Scientific Publications No. 148, edited by P. Vineis, N. Malats, M. Lang, A. d'Errico, N. Caporaso, J. Cuzick and P. Boffetta (Lyon: International Agency for Research on Cancer), pp. 251-270.
  • HOERING, H., ELLINGER, C., REINEKE, H. H., SCHIMMELPFENNIG, W., THIERFELDER, W. and DIETER, H. H. 1994, Gesundheitliche Bewertung von 35 Sprengstoff-typischen Verbindungen und Abbauprodukten, WaBoLu Hefte 6/1994 (Berlin: Institut für Wasser-, Boden- und Lufthygiene des Bundesgesundheitsamtes).
  • HOFFMANN, D. HOFFMANN, I. and EL-BAYOUMY, K. 2001, The less harmful cigarette: a controversial issue. A tribute to Ernst L. Wynder. Chemical Research in Toxicology, 14, 767-790.
  • HORAI, Y. and ISHIZAKI, T. 1985, Rapid and sensitive liquid Chromatographie method for the determination of dapsone and monoacetyldapsone in plasma and urine. Journal of Chromatography, 345, 447-452.
  • HOWARD, P. C., HECHT, S. S. and BELAND, F. A. (editors) 1990, Nitroarenes: Occurrence, Metabolism, and Biological Impact (New York: Plenum Press).
  • HSU, F. F., LAKSHMI, V. ROTHMAN, N., BHATNAGER, V. K., HAYES, R. B., KASHYAP, R., PARIKH, D. J., KASHYAP, S. K., TURK, J., ZENSER, T. and DAVIS, B. 1996, Determination of benzidine, N-acetylbenzidine, and N,N'-diacetylbenzidine in human urine by capillary gas chromatography negative ion chemical ionization mass spectrometry. Analytical Biochemistry, 234, 183-189.
  • HSU, T. M., ZHANG, Y. J. and SANTELLA, R. M. 1997, Immunoperoxidase quantitation of 4-aminobiphenyl- and polycyclic aromatic hydrocarbon-DNA adducts in exfoliated oral and urothelial cells of smokers and nonsmokers. Cancer Epidemiology, Biomarkers and Prevention, 6, 193-199.
  • HUITFELDT, H. S., BELAND, F. A., FULLERTON, N. F. and POIRIER, M. C. 1994, Immunohistochemical and microfluorometric determination of hepatic DNA adduct removal in rats fed 2-acetylaminofluorene. Carcinogenesis; 15, 2599-2603.
  • HUMPHREYS, W. G., KADLUBAR, F. F. and GUENGERICH, F. P. 1992, Mechanism of C8 alkylation of guanine residues by activated arylamines: evidence for initial adduct formation at the N7 position. Proceedings of the National Academy of Sciences of the USA, 89, 8278-8282.
  • IARC. 1993, Occupational Exposures of Hairdressers and Barbers and Personal Use of Hair Colourants; Some Hair Dyes, Cosmetic Colourants, Industrial Dyestuffs and Aromatic Amines, IARC Monographs: Evaluation of Carcinogenic Risks of Chemicals to Humans, Vol. 57 (Lyon: International Agency for Research on Cancer), pp. 43-267.
  • IPCS (INTERNATIONAL PROGRAMME ON CHEMICAL SAFETY). 1993, Biomarkers and risk assessment: concepts and principles, Environmental Health Criteria 155 (Geneva: World Health Organization).
  • IPPEN, H., 1994, Nitromoschus. Bundesgesundheitsblatt, 37, 255-260, 291-294.
  • IRUDAYA RAJ, P. P., LOURDUMARY, S., ASCHHO, M. and BALAKRISHNAN, S. 1983, A comparison of screening tests for dapsone in urine. Lepra India, 55, 528-538.
  • IZZOKTI, A. 1998, Detection of modified DNA nucleotides by postlabeling procedures. Toxicological Methods, 8, 175-205.
  • IZZOKTI, A., BALANSKY, R. M., DAGOSTINI, F., BENNICELLI, C., MYERS, S. R., GRUBBS, C. J., LUBRT, R. A., KELLO, G. J. and DE FLORA, S. 2001, Modulation of biomarkers by chemopreventive agents in smoke-exposed rats. Cancer Research, 61, 2472-2479.
  • JOPPICH-KUHN, R., HANGGI, R., SAGELSDORFF, P., SMITH, A. E., WEIDELI, H. J. and JOPPICH, M. 1997, Determination of dichlorobenzidine-hemoglobin adducts by GC/MS-NCI. International Archives of Occupational and Environmental Health, 69, 240-246.
  • JOSBPHY, P. D. 1996, The role of peroxidase-catalyzed activation of aromatic amines in breast cancer. Mutagenesis, 11, 3-7.
  • KADERLIK, K., TALASKA, G., DEBORD, D. G., OSORIO, A. M. and KADLUBAR, F. F. 1993, 4,4'-Methylenbis(2-chloroaniline)-DNA adduct analysis in human exfoliated cells by 32P-postlabeling. Cancer Epidemiology, Biomarkers and Prevention, 2, 63-69.
  • KADLUBAR, F. F. 1994, DNA adducts of carcinogenic aromatic amines. In DNA Adducts: Identification and Biological Significance, IARC Scientific Publications No. 125, edited by K. Hemminki, A. Dipple, D. E. G. Shuker, F. F. Kadlubar, D. Segerbäck and H. Bartsch (Lyon: International Agency for Research on Cancer), pp. 199-216.
  • KADLUBAR, F. F. and BELAND, F. 1985, Chemical properties of ultimate carcinogenic metabolites of arylamines and arylamides. In Polycyclic Hydrocarbons and Carcinogenesis, ACS Symposium Series No. 283, edited by P. G. Harvey (Washington, DC: American Chemical Society), pp. 341-370.
  • KADLUBAR, F. F., MILLER, J. A. and MILLER, E. C. 1978, Guanyl O6-arylamination and O6-arylation of DNA by the carcinogen N-hydroxy-1-naphthylamine. Cancer Research, 36, 3628-3638.
  • KADLUBAR, F. F., UNRUH, L. E., BELAND, F. A., STKAUB, K. M. and EVANS, F. E. 1980, In vitro reaction of the carcinogen, N-hydroxy-2-naphthylamine, with DNA at the C-8 and N2 atoms of guanine and the N6 atom of adenine. Carcinogenesis, 1, 139-150.
  • KADLUBAR, F. F., BELAND, F. A., BERANEK, D. T., DOOLEY, K. L., HEFLICH, R. H. and EVANS, F. E. 1982, Arylamine-DNA adduct formation in relation to urinary bladder Carcinogenesis and Salmonella typhimurium mutagenesis. In Environmental Mutagens, Carcinogens, edited by T. Sugimara, S. Kondo and H. Takebe (Tokyo: University of Tokyo Press), pp. 385-396.
  • KADLUBAR, F. F., TALASKA, G., LANG, N. P., BENSON, R. W. and ROBERTS, D. W. 1989, Assessment of exposure and susceptibility to aromatic amine carcinogens. In Methods for Detecting DNA Damaging Agents in Humans: Applications in Cancer Epidemiology and Prevention, IARC Scientific Publications No. 89, edited by H. Bartsch, K. Hemminki and I. K. O'Neill (Lyon: International Agency for Research on Cancer), pp. 166-180.
  • 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 Hb adduct formation, and liver and urinary bladder DNA adduct levels in beagle dogs given the carcinogen 4-aminobiphenyl. Cancer Research, 51, 4371-4377.
  • KADLUBAR, F. F., BUTLER, M. A., KADERLIK, K. R., CHOU, H. C. and LANG, N. P. 1992, Polymorphisms for aromatic amine metabolism in humans: relevance for human Carcinogenesis. Environmental Health Perspectives, 98, 69-74.
  • KÄFFERLEIN, H. U., GÖEN, T. and ANGERER, J. 1998, Musk xylene: analysis, occurrence, kinetics, and toxicology. Critical Reviews in Toxicology, 28, 431-476.
  • KAZANIS, S. and MCCLELLAND, R. A. 1992, Electrophilic intermediate in the reaction of glutathione and nitrosoarenes. Journal of the American Chemical Society, 114, 3052-3059.
  • KENNEDY, S. A., NOVAK, M. and KOLB, B. A. 1997, Reactions of ester derivatives of carcinogenic N-(4-biphenylyl)hydroxylamine and the corresponding hydroxamic acid with purine nucleosides. Journal of the American Chemical Society, 119, 7654-7664.
  • KENNELLY, J. C., BEUND, F. A., KADLUBAR, F. F. and MARTIN, C. N. 1984, Binding of N-acetylbenzidine and N,N'-diacetylbenzidine to hepatic DNA of rat and hamster in vivo and in vitro. Carcinogenesis, 5, 407-412.
  • KIESE, M. 1974, Methemogbinemia: A Comprehensive Treatise (Cleveland: CRC Press Inc.), pp. 1-258.
  • KING, R. S., TEITEL, C. H., SHADDOCK, J. G., CASCIANO, D. A. and KADLUBAR, F. F. 1999, Detoxification of carcinogenic aromatic and heterocyclic amines by enzymatic reduction of the N-hydroxy derivative. Cancer Letters, 143, 167-171.
  • KING, R., BONFIGLIO, R., FERNANDEZ-METZLER, C., MILLER-STEIN, C. and OLAH, T. 2000, Mechanistic investigation of ionization suppression in electrospray ionization. Journal of the American Society of Mass Spectrometry 11, 942-950.
  • KLEIN, M., VOIGTMANN, U., HAACK, T., ERDINGER, L. and BOCHE, G. 2000a, From mutagenic to non-mutagenic nitroarenes: effect of bulky alkyl substituents on the mutagenic activity of 4-nrtrobiphenyl in Salmonella typhimurium. Part I. Substituents ortho to the nitro group and in 2'-position. Mutation Research, 467, 55-68.
  • KLEIN, M., ERDINGER, L. and BOCHE, G. 2000b, From mutagenic to non-mutagenic nitroarenes: effect of bulky alkyl substituants on the mutagenic activity of nitroaromatics in Salmonella typhimurium. Part II. Substituents far away from the nitro group. Mutation Research, 467, 69-82.
  • KRIEK, E. 1971, On the mechanism of action of carcinogenic aromatic amines. H. Binding of N-hydroxy-N-acetyl-4-aminobiphenyl to rat-liver nucleic acids in vivo. Chemico-Biological Interactions, 3, 19-28.
  • KRIEK, E. 1972, Persistent binding of a new reaction product of the carcinogen N-hydroxy N-2-acetylaminofluorene with guanine in rat liver DNA in vivo. Cancer Research, 32, 2042-2048.
  • KRIEK, E. and HENGEVELD, G. M. 1978, Reaction products of the carcinogen N-hydroxy-4-acetylamino-4-fluorobiphenyl with DNA in liver and kidney of the rat. Chemico-Biological Interactions, 21, 179-201.
  • KRIEK, E. and WESTRA, J. G. 1971, Metabolic activation of aromatic amines and amides and interaction with nucleic acids. In Chemical Carcinogens and DNA, Vol. II, edited by P. L. Groover (Boca Raton: CRC Press), pp. 1-28.
  • LA, D. K. and FROINES, J. R. 1992a, Phosphorus-32-postlabelling analysis of DNA adducts from Fischer-344 rats administered 2,4-diaminotoluene. Chemico-Biological Interactions, 83, 121-134.
  • LA, D. K. and FROINES, J. R. 1992b, Comparison of DNA adduct formation between 2,4- and 2,6-dinitrotoluene by phosphorus-32-postlabelling analysis. Archives of Toxicology, 66, 633-640.
  • LA, D. K. and FROINES, J. R. 1993, Comparison of DNA binding between the carcinogen 2,6-dinitrotoluene and its noncarcinogenic analog 2,6-diaminotoluene. Mutation Research, 301, 79-85.
  • LA, D. K. and FROINES, J. R. 1994, Formation and removal of DNA adducts in Fischer-344 rats exposed to 2,4-diaminotoluene. Archives of Toxicology, 69, 8-13.
  • LAKSHMAN, M. K., KEELER, J. C., HILMER, J. H. and MARTIN, J. Q. 1999, Palladium-catalyzed C-N bond formation: facile and general synthesis of N6-aryl 2'-oxyadenosine analogues. Journal of the American Chemical Society, 121, 6090-6091.
  • LAKSHMI, V. M., HSU, F. F., DAVIS, B. B. and ZENSER, T. V. 2000, N-Acetylbenzidine-DNA adduct formation by phorbol 12-myristate-stimulated human polymorphonuclear neutrophils. Chemical Research in Toxicology, 13, 785-792.
  • LANCASTER, F. E. and LAWRENCE, J. F. 1992, Determination of total nonsulfonated aromatic amines in soft drinks and hard candies by reduction and derivatization followed by high-performance liquid chromatography. Food Additives and Contaminants, 9, 171-182.
  • LANDI, S. 2000, Mammalian class theta GST and differential susceptibility to carcinogens: a review. Mutation Research, 463, 247-283.
  • LANDI, M. T., ZOCCHETTI, C., BERNUCCI, L, KADLUBAR, F. F., TANNENBAUM, S., SKIPPER, P., BARTSCH, H., MALAVEILLE, C., SHIELDS, P., CAPORASO, N. E. and VINEIS, P. 1996, Cytochrome P4501A2: enzyme induction and genetic control in determining 4-aminobiphenyl-hemoglobin adduct levels. Cancer Epidemiology, Biomarkers and Prevention, 5, 693-698.
  • LANDI, M. T., SINHA, R., LANG, N. P. and KADLUBAR, F. F. 1999, Human cytochrome P4501A2. In Metabolic Polymorphisms and Susceptibility to Cancer, IARC Scientific Publications No. 148, edited by P. Vineis, N. Malats, M. Lang, A. d'Errico, N. Caporaso, J. Cuzick and P. Boffetta (Lyon: International Agency for Research on Cancer), pp. 173-195.
  • LANG, N. P., BUTLER, M. A., MASSENGILL, J., LAWSON, M., STOTTS, R. C., HAUER-JENSEN, M. and KADLUBAR, F. F. 1994, Rapid metabolic phenotypes for acetyltransferase and cytochrome P4501A2 and putative exposure to food-borne heterocyclic amines increase the risk for colorectal cancer or polyps. Cancer Epidemiology, Biomarkers and Prevention, 3, 675-682.
  • LAWRENCE, F. R. and MARSHALL, W. J. 1985, Aniline. In Ullmann's Encyclopedia of Industrial Chemistry, 5th edition, Vol. A2 (Weinheim: Wiley-VCH), pp. 303-312.
  • LASKO, D. D., HARVEY, S. C., MALAIKAL, S. B., KADLUBAR, F. F. and ESSIGMANN, J. M. 1988, Specificity of mutagenesis by 4-aminobiphenyl. A possible role for N-(deoxyadenosin-8-yl)-4-aminobiphenyl as a premutational lesion. Journal of Biological Chemistry, 263, 15429-15435.
  • LEWALTER, J. 1994, Anilin. In Biologische Arbeitstoff-Arbeitsstoff-Toterana-Werte (BAT-Werte) und Expositionsäquivalente für krebserzeugende Arbeitstoffe (EKA), edited by D. Henschler and G. Lehnert (Weinheim: VCH Verlagsgesellschaft), Band 1, 7. Lieferung, pp. 1-11.
  • LEWALTER, J. and GRIES, W. 2000, Haemoglobin adducts of aromatic amines: aniline, o-, m- and p-toluidine, o-anisidine, p-chloroaniline, a- and ß-naphthylamine, 4-aminodiphenyl, benzidine, 4,4'-diaminodiphenylmethane, 3,3 -dichlorobenzidine. Analytical Hazard Substances Biological Material, 7, 191-219.
  • LEWALTER, J. and KORALLUS, U. 1985, Blood protein conjugates and acetylation of aromatic amines. New findings on biological monitoring. International Archives of Occupational and Environmental Health, 56, 179-196.
  • LEWALTER, J. and KORALLUS, U. 1986, Erythrocyte protein conjugates as a principle of biological monitoring for pesticides. Toxicology Letters, 33, 153-165.
  • LEWALTER, J. and NEUMANN, H.G. 1996, Biologische Arbeitsstoff-Toleranzwerte (Biomonitoring): Teil VIII: Bewertung der Hintergrundbelastungen bei beruflich nicht-exponierten Personen. Arbeitsmedizin Sozialmedizin und Umweltmedizin, 31, 418-432.
  • LIN, J.-K., SCHMALL, B., SHARPE, I. D., MIURA, L, MILLER J. A. and MILLER, E. C. 1975, N-Substitution of carbon 8 in guanosine and deoxyguanosine by the carcinogen N-benzoyloxy-N-methyl-4-aminobenzene. Cancer Research, 35, 832-843.
  • LIN, D., LAY, J. O. JR, BRYANT, M. S., MALAVEILLE, C., FRIESEN, M., BARTSCH, H., LANG, N. P. and KADLUBAR, F. F. 1994, Analysis of 4-aminobiphenyl-DNA adducts in human urinary bladder and lung by alkaline hydrolysis and negative ion gas chromatography-mass spectrometry. Environmental Health Perspectives, 102, Supplement 6, 11-16.
  • LIND, P., DALENE, M., SKARPING, G. and HAGMAR, L. 1996, Toxicokinetics of 2,4- and 2,6-toluenediamine in hydrolysed urine and plasma after occupational exposure to 2,4- and 2,6-toluene diisocyanate. Occupational and Environmental Medicine, 53, 94-99.
  • LIPS, A. G. A. M., LAMEIJER, W., FOKKENS, R. H. and NIBBERING, N. M. M. 2001, Methodology for the development of a drug library based upon collision-induced fragmentation for the identification of toxicologically relevant drugs in plasma samples. Journal of Chromatography B, 759, 191-207.
  • LIU, Y.-Y., LU, A. Y. H., STEARNS, R. A. and CHIU, S. H. L. 1992, In vivo covalent binding of [14C]trinitrotoluene to proteins in the rat. Chemico-Biological Interactions, 82, 1-19.
  • LIU, Y.-Y., YAO, M., FANG, J.-L. and WANG, Y.-W. 1995, Monitoring human risk and exposure to trinitrotoluene (TNT) using haemoglobin adducts as biomarkers. Toxicology Letters, 77, 281-287.
  • LOTLIKAR, P. D., MILLER, E. C., MILLER, J. A. and MARGRETH, A. 1965, The enzymatic reduction of the N-hydroxy derivatives of 2-acetyl-aminofluorene and related carcinogens by tissue preparations. Cancer Research, 25, 1743-1752.
  • LUCERI, F., PIERACCINI, G., MONETI, G. and DOLARA, P. 1993, Primary aromatic amines from side- stream smoke are common contaminants of indoor air. Toxicology and Industrial Health, 9, 405-423.
  • MACLURE, M., BRYANT, M. S., SKIPPER, P. L. and TANNENBAUM, S. R. 1990, Decline of the hemoglobin adduct of 4-aminobiphenyl during withdrawal from smoking. Cancer Research, 50, 181-184.
  • MALAVEILLE, C., HAUTEFEUILLE, A., PIGNATELLI, B., TALASKA, G., VINEIS, P. and BARTSCH, H. 1998, Antimutagenic dietary phenolics as antigenotoxic substances in urothelium of smokers. Mutation Research, 402, 219-224.
  • MAO, B., GU, Z., GORIN, A., HINGERTY, B. E., BROYDE, S. and PATEL, D. J. 1997, Solution structure of the aminofluorene-stacked conformer of the syn-[AF]-C8-dG adduct positioned at a templateprimer junction. Biochemistry, 36, 14491-14501.
  • MAO, B., HINGERICY, B. E., BROYDE, S. and PATEL, D. J. 1998a, Solution structure of the aminofluorene [AF]-external conformer of the anti-[AF]-C8-dG adduct opposite dC in a DNA duplex. Biochemistry, 37, 95-106.
  • MAO, B., HINGERTY, B. E., BROYDE, S. and PATEL, D. J. 1998b, Solution structure of the aminofluorene [AF]-intercalated conformer of the syn-[AF]-C8-dG adduct opposite dC in a DNA duplex. Biochemistry, 37, 81-94.
  • MAPLES, K. R., EVER, P. and MASON, R. P. 1989, Aniline-phenylhydroxyl-amine-, nitrosobenzene- and nitrobenzene-induced hemoglobin thiyl free radical formation in vivo and in vitro. Molecular Pharmacology, 37, 311-318.
  • MARQUES, M. M., MOURATO, L. L. G., SANTOS, M. A. and BELAND, F. A. 1996, Synthesis, characterization, and conformational analysis of DNA adducts from methylated anilines present in tobacco smoke. Chemical Research in Toxicology, 9, 99-108.
  • MARQUES, M. M., MOURATO, L. L. G., AMORIM, M. T., SANTOS, M. A., MELCHIOR, W. B., JR and BELAND, F. A. 1997, Effect of substitution site upon the oxidation potentials of alkylanilines, the mutagenicities of N-hydroxyalkylanilines and the conformations of alkylaniline-DNA adducts. Chemical Research in Toxicology, 10, 1266-1274.
  • MARTIN, C. N., BELAND, F. A., ROTH, R. W. and KADLUBAR, F. F. 1982, Covalent binding of benzidine and N-acetylbenzidine to DNA at the C-8 atom of deoxyguanosine in vivo and in vitro. Cancer Research, 42, 2678-2696.
  • MARTIN, F. L., COLE, K. J., WILLIAMS, J. A., MILLAR, B. C., HARVEY, D., WEAVER, G., GROVER, P. L. and PHILLIPS, D. H. 2000, Activation of genotoxins to DNA-damaging species in exfoliated breast milk cells. Mutation Research, 470, 115-124.
  • 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. International Journal of Cancer, 75, 512-516.
  • MCCLELLAND, R. A., GADOSY, T. A. and REN, D. 1998, Reactivities of arylnitrenium ions with guanine derivatives and other nucleophiles. Canadian Journal of Chemistry, 76, 1327-1337.
  • MCCLELLAND, R. A., AHMAD, A., DICKS, A. P. and LICENCE, V. E. 1999, Spectroscopic characterization of the initial C8 intermediate in the reaction of the 2- fluorenylnitrenium ion with 2'-deoxyguanosine. Journal of the American Chemical Society, 121, 3303-3310.
  • MCLEOD, S., SINHA, R., KADLUBAR, F. F. and LANG, N. P. 1997, Polymorphisms of CYP1A1 and GSTM1 influence the in vivo function of CYP1A2. Mutation Research, 376, 135-142.
  • MEAL, P. F., COCKER, J., WILSON, H. K. and GILMOUR, J. M. 1981, Search for benzidine and its metabolites in urine of workers weighing benzidine-derived dyes. British Journal of Industrial Medicine, 38, 191-193.
  • MELCHIOR, W. B. JR, MARQUES, M. M. and BELAND F. A. 1994, Mutations induced by aromatic amine DNA adducts in pBR322. Carcinogenesis, 15, 889-899.
  • MEYER, U. A. and ZANGER, U. M. 1997, Molecular mechanisms of genetic polymorphisms of drug metabolism. Annual Review of Pharmacology and Toxicology, 37, 269-296.
  • MOURATO, L. L. G., BEUND, F. A. and MARQUES, M. M. 1999, 32P-Postlabeling of N-(deoxyguanosin-8-yl)arylamine adducts: a comparative study of labeling efficiencies. Chemical Research in Toxicology, 12, 661-669.
  • MILLER, J. A. 1994, Research in chemical carcinogenesis with Elizabeth Miller -- a trail of discovery with our associates. Drug Metabolism Reviews, 26, 1-36.
  • MOLLER L. 1994, In vivo metabolism and genotoxic effects of nitrated polycyclic aromatic hydrocarbons. Environmental Health Perspectives, 102, Supplement 4, 139-146.
  • MYERS, S. R., SPINNATO, J. A., PINORINI-GODLY, M. T., COOK, C., BOLES, B. and RODGERS, G. C. 1996, Characterization of 4-aminobiphenyl-hemoglobin adducts in maternal and fetal blood samples. Journal of Toxicology and Environmental Health, 47, 553-566.
  • NAGATA, K. and YAMAZOE, Y. (2000) Pharmacogenetics of sulfotransferase. Annual Review of Pharmacology and Toxicology, 40, 159-176.
  • NEUMANN, H. G. 1980, Biochemical effects and early lesions in regard to dose--response studies. Oncology, 37, 255-258.
  • NEUMANN, H.-G. 1984a, Analysis of hemoglobin as a dose monitor for alkylating and arylating agents. Archives of Toxicology, 56, 1-6.
  • NEUMANN, H.-G., 1984b, Dosimetry and dose response relationships. In Monitoring Human Exposure to Carcinogenic and Mutagenic Agents, IARC Scientific Publications No. 59, edited by A. Berlin, M. Draper, K. Hemminki and H. Vainio (Lyon: International Agency for Research on Cancer), pp. 115-126.
  • NEUMANN, H.-G. 1986, Toxication mechanisms in drug metabolism. Advances in Drug Research, 15, 1-28.
  • NEUMANN H. G., BIRNER G., KOWALLIK P., SCHUTZE D. and ZWIRNER-BAIER I. 1993, Hemoglobin adducts of TV-substituted aryl compounds in exposure control and risk assessment. Environmental Health Perspectives, 99, 65-69.
  • NEUMEISTER, C. E. 1991, Analysis of urine to monitor exposures to benzidine, o-dianisidine, o-tolidine, and 4,4'-methylenedianiline. Applied Occupational and Environmental Hygiene, 6, 953-958.
  • NOVAK, M. and KENNEDY, S. A. 1998, Inhibitory effect of DNA structure on the efficiency of reaction of guanosine moieties with a nitrenium ion. Journal of Physical Organic Chemistry, 11, 71-76.
  • O'BRIEN, P. J. 2000, Peroxidases. Chemico-Biological Interactions, 129, 113-139.
  • O'BRIEN, P. J., WONG, W. C., SILVA, J. and KHAN, S. 1990, Toxicity of nitrobenzene compounds towards isolated hepatocytes: dependence on reduction potential. Xenobiotica, 20, 945-955.
  • ORZECHOWSKI, A., SCHRENK, D., BOCK-HENNIG, B. S. and BOCK, K. W. 1994, Glucuronidation of carcinogenic arylamines and their N-hydroxy derivatives by rat and human phenol UDP-glucuronosyltransferase of the UGT1 gene complex. Carcinogenesis, 15, 1549-1553.
  • OSORIO, A. M., CLAPP, D., WARD, E., WILSON, H. K. and COCKER, J. 1990, Biological monitoring of a worker acutely exposed to MBOCA. American Journal of Industrial Medicine, 18, 577-589.
  • PARKES, H. G. and EVANS, A. E. J. 1984, Epidemiology of aromatic amine cancers. In Chemical Carcinogens, ACS Monograph 182, edited by C. E. Searle (Washington, DC: American Chemical Society), pp. 277-301.
  • PASTORELLI, R., CATENACCI, G., GUANCI, M., FANELLI, R., VALOTI, E., MINOIA, C. and AIROLDI, L. 1998, 3,4-Dichloroaniline-haemoglobin adducts in humans: preliminary data on agricultural workers exposed to propanil. Biomarkers, 3, 227-233.
  • PATEL, D. J., MAO, B., GU, Z., HINGERTY, B. E., GORIN, A., BASU, A. K. and BROYDE, S. 1998, Nuclear magnetic resonance solution structures of covalent aromatic amine-DNA adducts and their mutagenic relevance. Chemical Research in Toxicology, 11, 391-407.
  • PATRIANAKOS, C. and HOFFMANN, D. 1979, Chemical studies on tobacco smoke. LXIV. On the analysis of aromatic amines in cigarette smoke. Journal of Analytical Toxicology, 3, 150-154.
  • PELUSO, M., AIROLDI, L., ARMELLE, M., MARIONE, T., CODA, R., MALAVEILLE, C., GIACOMELLI, G., TERRONE, C., CASETTA, G. and VINEIS, P. 1998, White blood cell DNA adducts, smoking, and NAT2 and GSTM1 genotypes in bladder cancer: a case-control study. Cancer Epidemiology, Biomarkers and Prevention, 7, 341-346.
  • PELUSO, M., AIROLDI, L., MAGAGNOTTI, C., FIORINI, L., MUNNIA, A., HAUTEFEUILLE, A., MALAVEILLE, C. and VINEIS P. 2000, White blood cell DNA adducts and fruit and vegetable consumption in bladder cancer. Carcinogenesis, 21, 183-187.
  • PEREIRA, M. A., LIN, L.-H. C. and CHANG, L. W. 1981, Doses-dependency of 2-acetylaminofluorene binding to liver DNA and haemoglobin in mice and rats. Toxicology and Applied Pharmacology, 60, 472-478.
  • PHILLIPS, D. H. and CASTEGMARO, M. 1999, Standardization and validation of DNA adduct postlabelling methods: report of inter-laboratory trials and production of recommended protocols. Mutagenesis, 14, 301-315.
  • PHILIPPS, D. H., FARMER, P. B., BELAND, F. A., NATH, R. H. G., POIRIER, M. C., REDDY, M. V. and TURTELTAUB, K. W. 2000, Methods of DNA adduct determination and their application to testing compounds for genotoxicity. Environmental and Molecular Mutagenesis, 35, 222-233.
  • PINORINI-GODLY, M. T. and MYERS, S. R. 1996, HPLC and GC/MS determination of 4-aminobiphenyl haemoglobin adducts in fetuses exposed to the tobacco smoke carcinogen in utero. Toxicology, 107, 209-217.
  • 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. Chemical Research in Toxicology, 5, 749-755.
  • 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.
  • PROBST-HENSCH, N. M., BELL, D. A., WATSON, M. A., SKIPPER, P. L., TANNENBAUM, S. R. CHAN, K. K., Ross, R. K. and YU, M. C. 2000, N-Acetyltransferase 2 phenotype but not NAT1*10 genotype affects aminobiphenyl hemoglobin adduct levels. Cancer Epidemiology, Biomarkers and Prevention, 9, 619-623.
  • PUROHIT, V. and BASU, A. K. 2000, Mutagenicity of nitroaromatic compounds. Chemical Research in Toxicology, 13, 673-692.
  • RAMSEIER, C., SCHUEPBACH, M. and SEQUIN, U. 1987, HPLC determination of organic impurities in synthetic food dyes. Mitteilungen auf dem Gebiete der Lebensmitteluntersuchungen und Hygiene, 78, 401-406.
  • RICKERT, D. E. 1985, Toxicity of Nitroaromatic Compounds (Washington: Hemispher Publishing Cooperation).
  • RICKERT, D. E. 1987, Metabolism of nitroaromatic compounds. Drug Metabolism Reviews, 18, 23-53.
  • RICKERT, D. E., BUTTERWORTH, B. E. and POPP, J. A. 1984, Dinitrotoluene: acute toxicity, oncogenicity, genotoxicity and metabolism. Critical Reviews in Toxicology, 13, 217-234.
  • RIEDEL, J., BIRNER, G., VAN DORP, C., NEUMANN, H. G. and DEKANT, W. 1999, Haemoglobin binding of a musk xylene metabolite in man. Xenobiotica, 29, 573-582.
  • RIETJENS, I. M. C. M., TYRAKOWSKA, B., VEEGER, C. and VERVOORT, J. 1990, Reaction pathways for biodehalogenation of fluorinated anilines. European Journal of Biochemistry, 194, 945-954.
  • RIFFELMANN, M., MÜLLER, G., SCHMIEDING, W., POPP, W. and NORPOTH, K. 1995, Biomonitoring of urinary aromatic amines and arylamine hemoglobin adducts in exposed workers and nonexposed control persons. International Archives of Occupational and Environmental Health, 68, 36-43.
  • RIMKUS, G., RIMKUS, B. and WOLF, M. 1994, Nitro musks in human adipose tissue and breast milk. Chemosphere, 28, 421-432.
  • 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. Chemical Research in Toxicology, 1, 22-24.
  • RITTER, J. K. 2000, Roles of glucuronidation and UDP-glucuronosyltransferases in xenobiotic bioactivation reactions. Chemico-Biological Interactions, 129, 171-193.
  • ROBERT, A., Ducos, P. and FRANCIN, J. M. 1999a, Biological monitoring of workers exposed to 4,4'-methylene-bis-(2-orthochloroaniline) (MOCA). I. A new and easy determination of 'free' and 'total' MOCA in urine. International Archives of Occupational and Environmental Health, 72, 223-228.
  • ROBERT, A., DUCOS, P. and FRANCIN, J. M. 1999b, Biological monitoring of workers exposed to 4,4'-methylene-bis-(2-orthochloroaniline) (MOCA). H. Comparative interest of 'free' and 'total' MOCA in the urine of exposed workers. International Archives of Occupational and Environmental Health, 72, 229-237.
  • 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 Research, 48, 6336-6342.
  • ROBERTS, D. W., BENSON, R. W., HINSON, J. A. and KADLUBAR, F. F. 1991, Critical considerations in the immunochemical detection and quantitation of antigenic biomarkers. Biomedical and Environmental Science, 4, 113-129.
  • ROMANO, G., MANCINI, R., FEDELE, P., CURIGLIANO, G., FLAMINI, G., GIOVAGNOLI, M. R., MALARA, N., BONINSEGNA, A., VECCHIONE, A., SANTELLA, R. M. and CITTADINI, A. 1997, Immunohistochemical analysis of 4-aminobiphenyl-DNA adducts in oral mucosal cells of smokers and nonsmokers. Anticancer Research, 17, 2827-2830.
  • ROMANO, G., GARAGNANI, L., BONINSEGNA, A., FERRARI, P., FLAMINI, G., DE GAETANI, C., SGAMBAIO, A., GIOVANNI, F., CURIGLIANO, G., FERRETTI, G., CITTADINI, A. and TRENTINI, G. 1999, Analysis of 4-aminobiphenyl-DNA adducts and p53 alterations in urinary bladder carcinoma. Anticancer Research, 19, 4571-4576.
  • ROSENBERG, C. and SAVOLAINEN, H. 1986, Determination of occupational exposure to toluene diisocyanate by biological monitoring. Journal of Chromatography, 367, 385-392.
  • ROSENBLATT, D. H., BURROWS, E. P., MITCHELL, W. R. and FARMER, D. L. 1991, Organic explosives and related compounds. In Handbook of Environmental Chemistry, edited by O. Hutzinger (Berlin, Heidelberg: Springer-Verlag).
  • ROTHMAN, N., BHATNAGAR, V. K., HAVES, R. B., ZENSER, T. V., KASHYAP, S. K., BUTLER, M. A., BELL, D. A., LAKSHMI, V., JAEGER, M., KASHYAP, R., HIRVONEN, A., SCHULTE, P. A., DOSEMECI, M., HSU, F., PARIKH, D. J., DAVIS, B. B. and TALASKA, G. 1996a, The impact of interindividual variation in NAT2 activity on benzidine urinary metabolites and urothelial DNA adducts in exposed workers. Proceedings of the National Academy of Sciences of the USA, 93, 5084-5089.
  • ROTHMAN, N., HAYBS, R. B., ZENSER, T. V., DEMARINI, D. M., BI, W., HIRVONEN, A., TALASKA, G., BHATNAGAR, V. K., CAPORASO, N. E., BROOKS, L. R., LAKSHMI, V. M., FENG, P., KASHYAP, S. K., YOU, X., EISCHBN, B. T., KASHYAP, R., SHELTON, M. L., HSU, F. F., JAEGER, M., PARIKH, D. J., DAVIS, B. B., YIN, S. and BELL, D. A. 1996b, The glutathione S-transferase M1 (GSTM1) null genotype and benzidine-associated bladder cancer, urine mutagenicity, and exfoliated urothelial cell DNA adducts. Cancer Epidemiology, Biomarkers and Prevention, 5, 979-983.
  • ROTHMAN, N., TALASKA, G., HAVES, R. B., BHATNAGAR, V. K., BELL, D. A., LAKSHMI, V. M., KASHYAP, S. K. DOSEMECI, M., KASHYAP, R., HSU, F. F., JAEGER, M., HIRVONEN, A., PARIKH, D. J., DAVIS, B. B. and ZENSER, T. V. 1997, Acidic urine pH is associated with elevated levels of free urinary benzidine and N-acetylbenzidine and urothelial cell DNA adducts in exposed workers. Cancer Epidemiology, Biomarkers and Prevention, 6, 1039-1042.
  • SABBIONI, G. 1992, Quantitative structure activity relationship of the N-oxidation of aromatic amines. Chemico-Biological Interactions, 81, 91-117.
  • SABBIONI, G. 1994a, Hemoglobin binding of arylamines and nitroarenes: molecular dosimetry and quantitative structure activity relationships. Environmental Health Perspectives, 102, Supplement 6, 61-67.
  • SABBIONI, G. 1994b, Hemoglobin binding of nitroarenes and quantitative structure-activity relationships. Chemical Research in Toxicology, 7, 267-274.
  • SABBIONI, G. and BEYERBACH, A. 1995, Determination of hemoglobin adducts of arylamines in humans. Journal of Chromatography B, 667, 75-83.
  • SABBIONI, G. and BEYERBACH, A. 2000, Hemoglobin adducts of aromatic amines: diamines and polyaromatic amines. Journal of Chromatography B, 744, 377-387.
  • SABBIONI, G. and NEUMANN, H.-G. 1990a, Quantification of haemoglobin binding of 4,4'-methylenebis(2-chloroaniline) (MOCA) in rats. Archives of Toxicology, 64, 451-458.
  • SABBIONI, G. and NEUMANN, H.-G. 1990b, Biomonitoring of arylamines: hemoglobin adducts of urea and carbamate pesticides. Carcinogenesis, 11, 111-115.
  • SABBIONI, G. and SCHÜTZE, D. 1998, Hemoglobin binding of bicyclic aromatic amines. Chemical Research in Toxicology, 11, 471-483.
  • SABBIONI, G. and SEPAI, O. 1995, Comparison of hemoglobin binding, mutagenicity and carcinogenicity of arylamines and nitroarenes. Chimia, 49, 374-380.
  • SABBIONI, G., WEI, J. and LIU, Y.-Y. 1996, Determination of hemoglobin adducts in workers exposed to 2,4,6-trinitrotoluene. Journal of Chromatography B, 682, 243-248.
  • SAGELSDORFF, P., HAENGGI, R., HEUBERGER, B., JOPPICH-KUHN, R., JUNG, R., WEIDELI, H. J. and JOPPICH, M. 1996, Lack of bioavailability of dichlorobenzidine form diarylide azo pigments: molecular dosimetry for hemoglobin and DNA adducts. Carcinogenesis, 17, 507-514.
  • SANTELLA, R. M. 1999, Immunological methods for detection of carcinogen-DNA damage in humans. Cancer Epidemiology, Biomarkers and Prevention, 8, 733-739.
  • SCHEEPERS, P. T. J., VELDERS, D. D., STRAETEMANS, M. M. E., OUWERKERK, J. C., VAN VLIET, L. A. and Bos. R. P. 1993, Solid-phase extraction and gas chromatographic-mass spectrometric determination after hydrolysis of 2-aminofluorene Hb adducts in blood of rats. Journal of Chromatography B, 619, 215-221.
  • SCHEEPERS, P. T. J., VELDERS, D. D., STEENWINKEL, M.-J. S. T., VAN DELFT, J. H. M., DRIESSEN, W., STOAETEMANS, M. M. E., BAAN, R. A., KOOPMAN, J. P., NOORDHOEK, J. and Bos, R. P. 1994, Role of the intestinal microflora in the formation of DNA and hemoglobin adducts in rats treated with 2-nitrofluorene and 2-aminofluorene by gavage. Carcinogenesis, 15, 1433-1441.
  • SCHÜTZE, D., SEPAI, O., J. LEWALTER, L. MIKSCHE, D. HENSCHLER and SABBIONI, G. 1995, Biomonitoring of workers exposed to 4,4'-methylenedianiline or 4,4'-methylenediphenyl diisocyanate. Carcinogenesis, 16, 573-582.
  • SCHUTTE, D., SAGELSDORFF, P., SEPAI, O. and SABBIONI, G. 1996, Synthesis and quantification of DNA adducts of 4,4'-methylenedianiline. Chemical Research in Toxicology, 9, 1103-1112.
  • SCHWENECKE, H. and MAYER, D. 1985, Benzidine and benzidine derivatives. In Ullmann's Encyclopedia of Industrial Chemistry, 5th edition, Vol. A3 (Weinheim: Wiley-VCH), pp. 539-554.
  • SEGERBACK, D. and KADLUBAR, F. F. 1992, Characterization of 4,4'-methylenebis(2-chloroaniline)-DNA adducts formed in vivo and in vitro. Carcinogenesis, 13, 1587-1592.
  • SEPAI, O., HBNSCHLER, D., CZECH, S., ECKERT, P. and SABBIONI, G. 1995a, Exposure to toluene diamines from polyurethane-coated breast implants. Toxicology Letters, 77, 371-378.
  • SEPAI, O., HENSCHLER, D. and SABBIONI, G. 1995b, Albumin adducts, hemoglobin adducts and urinary metabolites in workers exposed to 4,4'-methylenediphenyl diisocyanate. Carcinogenesis, 16, 2583-2587.
  • SHAPIRO, R., STEPHEN, E., HINGERTY, B. E. and BROYDE, S. 1998, Effect of ring size on conformations of aromatic amine-DNA adducts: the aniline-C8 guanine adduct resides in the B-DNA major groove. Chemical Research in Toxicology, 11, 335-341.
  • SILK, N. A., LAY, J. O. JR and MARTIN, C. N. 1989, Covalent binding of 4,4'-methylenebis-(2-chloroaniline) to rat liver DNA in vivo and of its N-hydroxylated derivative to DNA in vitro. Biochemical Pharmacology, 38, 279-287.
  • SKIPPER, P. L. 1996, Influence of tertiary structure on nucleophilic substitution reactions of proteins. Chemical Research in Toxicology, 9, 918-923.
  • SKIPPER, P. L. and GROOPMAN, J. D. (editors) 1991, Molecular Dosimetry of Human Cancer: Epidemiological, Analytical and Social Considerations (London: CRC Press), pp. 263-280.
  • SKIPPER, P. L. and STILLWELL, W. G. 1994, Aromatic-amine Hb adducts. Methods in Enzymology, 231, 643-649.
  • SKIPPER, P. L. and TANNENBAUM, S. R. 1990, Protein adducts in molecular dosimetry of chemical carcinogens. Carcinogenesis, 11, 507-518.
  • SKIPPER, P. L. and TANNENBAUM, S. R. 1994, Molecular dosimetry of aromatic amines in human populations. Environmental Health Perspectives, 102, Supplement 6, 17-21.
  • SKIPPER, P. L., GREEN, L. G., BRYANT, M. S. and TANNENBAUM, S. R. 1984, Monitoring exposure to 4-aminobiphenyl via blood protein adducts. In Monitoring Human Exposure to Carcinogenic and Mutagenic Agents, IARC Scientific Publications No. 59, edited by A. Berlin, M. Draper, K. Hemminki and H. Vainio (Lyon: International Agency for Research on Cancer), pp. 115-126.
  • SKIPPER, P. L., OBIEDZINSKI, M. W., TANNENBAUM, S. R., MILLER, D. W., MITCHCM, R. K. and KADLUBAR, F. F. 1985, Identification of the major serum albumin adduct formed by 4-aminobiphenyl in vivo in rats. Cancer Research, 45, 5122-5127.
  • SKIPPER, P. L., BRYANT, M. S. and TANNENBAUM, S. R. 1988, Determination of human exposure to carcinogenic aromatic amines from hemoglobin adducts in selected population groups. In Carcinogenic Mutagenic Responses to Aromatic Amines and Nitroarenes, edited by C. M. King, L. J. Romano and D. Schuetzle (New York: Elsevier), pp. 65-71.
  • SOGLIA, J. R., TURESKY, R. J., PAEHLER, A. and VOUROS, P. 2001, Quantification of the heterocyclic aromatic amine DNA adduct N-(deoxyguanosin-8-yl)-2-amino-3-methylimidazo[4,5-fJquinoline in livers of rats using capillary liquid chromatography/microelectrospray mass spectrometry: a dose-response study. Analytical Chemistry, 73, 2819-2827.
  • SORLIE, T., MARTEL-PLANCHE, G., HAINALT, P., LEWALTER, J., HOLM, R., BORRESEN-DALE, A. L. and MONTESANO, R. 1998, Analysis of p53, p16MTS, p21WAF1 and H-ras in archived bladder tumours from workers exposed to aromatic amines. British Journal of Cancer, 77, 1573-1579.
  • STAUTMAN, E. R. 1990, Covalent modification reactions are marking steps in protein turnover. Biochemistry, 29, 6323-6331.
  • STANTON, C. A., CHOW, F. L., PHILIPS, D. H., GROVER, P. L., GARNER, R. C. and MARTIN, C. N. 1985, Evidence for N-(deoxyguanosin-8-yl)-1-aminopyrene as a major DNA adduct in female rats treated with 1-nitropyrene. Carcinogenesis, 6, 535-538.
  • STILLWELL, W. G., BRYANT, M. S. and WISHNOK, J. S. 1987, GC/MS analysis of biologically important aromatic amines. Application to human dosimetry. Biomedical and Environmental Mass Spectrometry, 14, 221-227.
  • SUZUKI, J., MECURO, S.-I., MORITA, O., HIRAYAMA, S. and SUZUKI, S. 1989, Comparison of in vivo binding and amino compounds to rat hemoglobin. Biochemical Pharmacology, 38, 3511-3519.
  • TALASKA, G., DOOLEY, K. L. and KADLUBAR, F. F. 1990, Detection and characterization of carcinogen-DNA adducts in exfoliated urothelial cells from 4-aminobiphenyl-treated dogs by 32P-postlabelling and subsequent thin-layer and high-pressure liquid chromatography. Carcinogenesis, 11, 639-646.
  • TALASKA, G., AL-JUBURI, A. Z. S. S. and KADLUBAR, F. F. 1991a, Smoking related carcinogen-DNA adducts in biopsy samples of human urinary bladder: identification of n-(deoxyguanosin-S-yl)4-aminobiphenyl as a major adduct. Proceedings of the National Academy of Sciences of the USA, 88, 5350-5354.
  • TALASKA, G., SCHAMER, M., SKIPPER, P., TANNENBAUM, S., CAPORASO, N., UNRUH, L., KADLUBAR, F. F., BARTSCH, H., MAIAVEILLE, C. and VINEIS, P. 1991b, Detection of carcinogen-DNA adducts in exfoliated urothelial cells of cigarette smokers: association with smoking, hemoglobin adducts, and urinary mutagenicity. Cancer Epidemiology, Biomarkers and Prevention, 1, 61-66.
  • TALASKA, G., ROH, J. H. and GETEK, T. 1992, 32P-postlabelling and mass spectrometric methods for analysis of bulky, polyaromatic carcinogen-DNA adducts in humans. Journal of Chromatography, 580, 293-323.
  • TALASKA, G., SCHAMER, M., SKIPPER, P., TANNENBAUM, S., CAPORASO, N., KADLUBAR, F., BARTSCH, H. and VINEIS, P. 1993, Carcinogen-DNA adducts in exfoliated urothelial cells: techniques for noninvasive human monitoring. Environmental Health Perspectives, 99, 289-291.
  • TALASKA, G., SCHAMER, M., CASETTA, G., TIZZANI, A. and VINEIS, P. 1994, Carcinogen-DNA adducts in bladder biopsies and urothelial cells: a risk assessment exercise. Cancer Letters, 84, 93-97.
  • TANG, D., WARBURTON, D., TANNENBAUM, S. R., SKIPPER, P., SANTELLA, R. M., CEREIJIDO, G. S., CRAWFORD, F. G. and PERERA, F. P. 1999, Molecular and genetic damage from environmental tobacco smoke in young children. Cancer Epidemiology, Biomarkers and Prevention, 8, 427-431.
  • TANNENBAUM, S. R., BRYANT, M. S., SKIPPER, P. L. and MACLURE, M. 1986, Hemoglobin adducts of tobacco-related aromatic amines: application to molecular epidemiology. Banbury Report, 26, 63-75.
  • TARPLEY, W. G., MILLER, J. A. and MILLER, E. C. 1980, Adducts from the reaction of N-benzoyloxy-N-methyl-4-aminobenzene with deoxyguanosine or DNA in vitro and from hepatic DNA of mice treated with N-methyl- or N,N-dimethyl-4-aminoazobenzene. Cancer Research, 40, 2493-2499.
  • THOMPSON, P. A., SEYEDI, F., LANG, N. P., MACLEOD, S. L., WOGAN, G. N., ANDERSON, K. E., TANG, Y.-M., COLES, B. and KADLUBAR, F. F. 1999, Comparison of DNA adduct levels associated with exogenous and endogenous exposures in human pancreas in relation to metabolic genotype. Mutation Research, 424, 263-274.
  • TIMBRELL, J. A. 1998, Biomarkers in toxicology. Toxicology, 129, 1-12.
  • TROESTER, M. A., KUPPER, L. L. and RAPPAPORT, S. M. 2001, Comparison of non-linear and linear models for estimating haemoglobin adduct stability. Biomarkers, 6, 251-261.
  • TSURATA, Y., SUBRAHMANYAN, V. V., MARSHALL, W. and O'BRIEN, P. J. 1985, Peroxidase-mediated irreversible binding of arylamine carcinogens to DNA in intact polymorphonuclear leukocytes activated by a tumor promoter. Chemico-Biological Interactions, 53, 1618-1622.
  • TUKEY, R. H. and STRASSBURG, C. P. 2000, Human UDP-glucuronosyltransferase: metabolism, expression, and disease. Annual Review of Pharmacology and Toxicology, 40, 581-616.
  • TULLIS, D. L., STOAUB, K. M. and KADLUBAR, F. F. 1981, A comparison of the carcinogen-DNA adducts formed in rat liver in vivo after administration of a single or multiple doses of N-methyl4-aminoazobenzene. Chemico-Biological Interactions, 38, 15-27.
  • TULLIS, D. L., DOOLEY, K. L., MILLER, D. W., BAETCKE, K. P. and KADLUBAR, F. F. 1987, Characterization and properties of the DNA adducts formed from N-methyl-4-aminoazobenzene in rats during a carcinogenic treatment regimen. Carcinogenesis, 8, 577-583.
  • TURNER, M. J. JR, LEVINE, R. J., NYSTROM, D. D., CRUME, Y. S. and RICKERT, D. E. 1985, Identification and quantification of urinary metabolites of dinitrotoluenes in occupationally exposed humans. Toxicology and Applied Pharmacology, 80, 166-174.
  • VAN BEKKUM, Y. M., VAN DEN BROEK, P. H. H., SCHEEPERS, P. T. J., NORDHOEK, J. and Bos, R. P. 1999, Biological fate of [14C]-1-nitropyrene in rats following intragastric administration. Chemico- Biological Interactions, 117, 15-33.
  • VAN DE POLL, M. L. M., TIJDENS, R. B., VONDRACEK, P., BRUINS, A. P., MEIJER, D. K. F. and MEERMAN, J. H. N. 1989, The role of sulfation in the metabolic activation of N-hydroxy-4-fluoro-4-acetylaminobiphenyl. Carcinogenesis, 10, 2285-2291.
  • VAN DE POLL, M. L. M., VENIZELOS, V. and MEERMAN, J. H. N. 1990, Sulfation-dependent formation of N-acetylated and deacetylated DNA adducts of N-hydroxy-4-acetylaminobiphenyl in male rat liver in vivo and in isolated hepatocytes. Carcinogenesis, 11, 1775-1781.
  • VAUGHAN, G. T. and KENYON, R. S. 1996, Monitoring for occupational exposure to 4,4'-methylenebis(2-chloroaniline) by gas chromatographic-mass spectrometric analysis of haemoglobin adducts, blood, plasma and urine. Journal of Chromatography B, 678, 197-204.
  • VERMEULEN, N. P., BESSEMS, J. G. and VAN DE STRAAT, R. 1992, Molecular aspects of paracetamol-induced hepatotoxicity and its mechanism-based prevention. Drug Metabolism Reviews, 24, 367-407.
  • VINEIS, P. 1997, Sources of variation in biomarkers. In Application of Biomarkers in Cancer Epidemiology, IARC Scientific Publications No. 142, edited by P. Toniolo, P. Boffetta, D. E. G. Shuker, N. Rothman, B. Hulka and N. Pearce (Lyon: International Agency for Research on Cancer), pp. 59-72.
  • VINEIS, P. and MARTONE, T. 1996, Molecular epidemiology of bladder cancer. Annali dell' Istituto Superiors di Sanitd, 32, 21-27.
  • VINEIS, P., CAPORASO, N., TANNENBAUM, S. R., SKIPPER, P. L., GLOGOWSKI, J., BARTSCH, H., CODA, M., TALASKA, G. and KADLUBAR, F. 1990, Acetylation phenotype, carcinogen-hemoglobin adducts, and cigarette smoking. Cancer Research, 50, 3002-3004.
  • VINEIS, P. TALASKA, G., MALAVEILLE, C., BARTSCH, H., MARIONE, T., SITHISARANKUL, P. and STRICKLAND, P. 1996, DNA adducts in urothelial cells: relationship with biomarkers of exposure to arylamines and polycyclic aromatic hydrocarbons from tobacco smoke. International Journal of Cancer, 65, 314-316.
  • VINEIS, P., KOGEVINAS, M., SIMONATO, L., BRENNAN, P. and BOFKBTTA, P. 2000, Levelling-off of the risk of lung and bladder cancer in heavy smokers: an analysis based on multicentric case-control studies and a metabolic interpretation. Mutation Research, 463, 103-110.
  • VOGT, P. F. and GERULIUS, J. J. 1985, Amines, aromatic. In Ullmann's Encyclopedia of Industrial Chemistry, 5th edition, Vol. A2 (Weinheim: Wiley-VCH), pp. 37-53.
  • WARD, E. M. 1997, Comments to: Biological monitoring of aromatic amine exposures at a chemical plant with a known bladder excess. Journal of the National Cancer Institute, 89, 734-736.
  • WARD, E., CLAPP, D., TOLOS, W. and GROTH, D. 1986, Efficacy of urinary monitoring for 4,4'-methylenebis(2-chloroaniline). Journal of Occupational Medicine, 28, 637-642.
  • WARU, E., SMITH, A. B. and HALPERIN, W. 1987, 4,4'-Methylenebis(2-chloroaniline): an unregulated carcinogen. American Journal of Industrial Medicine, 12, 537-549.
  • WARD, E. M., SABBIONI, G., DEBORD, D. G., TEASS, A. W., BROWN, K., TALASKA, G., ROBERTS, D., RUDER, A. and STREICHER, R. P. 1996, Biological monitoring of aromatic amine exposures at a chemical plant with a known bladder excess. Journal of the National Cancer Institute, 88, 1040-1052.
  • 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 Research, 51, 5219-5223.
  • WESTRA, J. G., KRIEK W. and HITTENHAUSEN, H. 1976, Identification of the persistently bound form of the carcinogen N-acetyl-2-aminofluorene to rat liver in vivo. Chemico-Biological Interactions, 15, 149-164.
  • WESTRA, J. G., FLAMMANG, T. J., FULLERTON, N. F. BELAND, F. A., WEIS, C. C. and KADLUBAR, F. F. 1985, Formation of DNA adducts in vivo in rat liver and intestinal epithelium after administration of the carcinogen 3,2-dimethyl-4-aminobiphenyl and its hydroxamic acid. Carcinogenesis, 6, 37-44.
  • WHETSTINE, J. R. YUEH, M.-F., HOPP, K. A., MCCARVER, D. G., WILLIAMS, D. E., PARK, C.-S., KANG, J. H. CHA, Y.-N., DOLPHIN, C. T., SHEPHARD, E. A., PHILLIPS, I. R. and HINES, R. N. 2000, Ethnic differences in human flavin-containing monooxygenase 2 (FMO2) polymorphisms: detection of expressed protein in African-Americans. Toxicology and Applied Pharmacology, 168, 216-224.
  • WHYSNER, J., VERNA, L. and WILLIAMS, G. M. 1996, Benzidine mechanistic data and risk assessment: species- and organ-specific metabolic activation. Pharmacology and Therapeutics, 71, 107-126.
  • WIESE, F. W., THOMPSON, P. A. and KADLUBAR, F. F. 2001, Carcinogen substrate specificity of human COX-1 and COX-2. Carcinogenesis, 22, 5-10.
  • WILLIAMS, J. A. 2001, Single nucleotide polymorphisms, metabolic activation and environmental Carcinogenesis: why molecular epidemiologists should think about enzyme expression. Carcinogenesis, 22, 209-214.
  • WILLIAMS, J. A. and PHILLIPS, D. H. 2000, Mammary expression of xenobiotic metabolizing enzymes and their potential role in breast cancer. Cancer Research, 60, 4667-4677.
  • WILSON, P. M., QUE HEE, S. S. and FROINES, J. R. 1995, Determination of hemoglobin adduct levels of the carcinogen 2,4-diaminotoluene using gas chromatography-electron impact positive-ion mass spectrometry. Journal of Chromatography B, 667, 166-172.
  • WILSON, P. M., LA, D. K. and FROINES, J. R. 1996, Hemoglobin and DNA adduct formation in Fischer-344 rats exposed to 2,4- and 2,6-toluene diamine. Archives of Toxicology, 70, 591-598.
  • WOOLLEN, B. H., HALL, M. G., CRAIG, R. and STEEL, G. T. 1985, Dinitrotoluene: an assessment of occupational absorption during the manufacture of blasting explosives. International Archives of Occupational and Environmental Health, 55, 319-330.
  • WORMHOUDT, L. W., COMMANDEUR, J. N. M. and VERMEULEN, N. P. E. 1999, Genetic polymorphisms of human N-acetyltransferase, cytochrome P450, glutathione-S-transferase, and epoxide hydrolase enzymes: relevance to xenobiotic metabolism and toxicity. Critical Reviews in Toxicology, 29, 59-154.
  • YAMAZOE, Y., MILLER, D. W., WEIS, C. C., DOOLEY, K. L., ZENSER, T. V., BELAND, F. A. and KADLUBAR, F. F. 1985, DNA adducts formed by ring-oxidation of the carcinogen 2-naphthylamine with prostaglandin H synthase in vitro and in the dog urothelium in vivo. Carcinogenesis, 6, 1379-1387.
  • YAMAZOE, Y., ROTH, R. W. and KADLUBAR, F. F. 1986, Reactivity of benzidine diimine with DNA to form N-(deoxyguanosin-8-yl)-benzidine. Carcinogenesis, 7, 179-182.
  • YAMAZOE, Y., ZENSER, T. V., MILLER, D. W. and KADLUBAR, F. F. 1988, Mechanism of formation and structural characterization of DNA adducts derived from peroxidative activation of benzidine. Carcinogenesis, 9, 1635-1641.
  • YINON, J. 1990, Toxicity and Metabolism of Explosives (Boca Raton: CRC Press).
  • YINON, J. and HWANG, D. G. 1986, Detection of TNT and its metabolites in body fluids of laboratory animals and in occupationally exposed humans. Journal of Energy Material, 4, 305-313.
  • YOSHIDA, T., TABUCHI, T. and ANDOH, K. 1993, Pharmacokinetic study p-chloronitrobenzene in humans suffering from acute poisoning. Drug Metabolism and Disposition, 21, 1142-1146.
  • YU, M. C., Ross, R. K., CHAN, K. K., HENDERSON, B. E., SKIPPER, P. L., TANNENBAUM, S. R. and COETZEE, G. A. 1995, Glutathione S-transferase Ml genotype affects aminobiphenyl-hemoglobin adduct levels in white, black and Asian smokers and nonsmokers. Cancer Epidemiology, Biomarkers and Prevention, 4, 861-864.
  • YUN, C. H., SHIMADA, T. and GUENGERICH, F. P. 1992, Contributions of human liver cytochrome P450 enzymes to the N-oxidation of 4,4'-methylene-bis(2-chloroaniline). Carcinogenesis, 13, 217-222.
  • ZENSER, T. V., LAKSHMI, V. M., RUSTAN, T. D., DOLL, M. A., DEITZ., A. C., DAVIS, B. B. and HEIN, D. W. 1996, Human N-acetylation of benzidine: role of NAT1 and NAT2. Cancer Research, 56, 3941-3947.
  • ZHOU, Q., TALASKA, G., JAEGER, M., BHATNAGAR, V. K., HAVES, R. B., ZENZER, T. V., KASHYAP, S. K., LAKSHMI, V. M., KASHYAP, R., DOSEMECI, M., HSU, F. F., PARIKH, D. J., DAVIS, B. and ROTHMAN, N. 1997, Benzidine-DNA adduct levels in human peripheral white blood cells significantly correlate with levels in exfoliated urothelial cells. Mutation Research, 393, 199-205.
  • ZIEGLER, D. M. 1993, Recent studies on the structure and function of multisubstrate flavin-containing monooxygenases. Annual Review of Pharmacology and Toxicology, 33, 179-199.
  • ZIEGLER, D. M., ANSHER, S. S., NAGATA, T., KAULUBAR, F. F. and JAKOBY, W. B. 1988, N-Methylation: potential mechanism for metabolic activation of carcinogenic primary arylamines. Proceedings of the National Academy of Sciences of the USA, 85, 2514-2517.
  • ZCIOEMA, J., HILBERS-MODDERMAN, E. S. and MERKUS, F. W. 1986, Clinical pharmacokinetics of dapsone. Clinical Pharmacokinetics, 11, 299-315.
  • ZWIRNER-BAIER, I. and NEUMANN, H.-G. 1994, Biomonitoring of aromatic amines. IV: Use of Hb adducts to demonstrate the bioavailability of cleavage products from diarylide azo pigments in vivo. Archives of Toxicology, 68, 8-14.
  • ZWIRNER-BAIER, I. and NEUMANN, H. G. 1998, Biomonitoring of aromatic amines. V: Acetylation and deacetylation in the metabolic activation of aromatic amines as determined by Hb binding. Archives of Toxicology, 72, 499-504.
  • ZWIRNER-BAIER, I. and NEUMANN, H.-G. 1999, Polycyclic nitroarenes (nitro-PAHs) as biomarkers of exposure to diesel exhaust. Mutation Research, 441, 135-144.
  • ZWIRNER-BAIER, I., KORDOWICH, F.-J. and NEUMANN, H.-G. 1994, Hydrolyzable hemoglobin adducts of polyfunctional monocyclic N-substituted arenes as dosimeters of exposure and markers of metabolism. Environmental Health Perspectives, 102, Supplement 6, 43-45.

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