47
Views
14
CrossRef citations to date
0
Altmetric
Research Article

The Tissue Distribution and the Tissue Specificity of Bioactivation of Some Tobacco-Specific and Some Other N-Nitrosamines

Pages 265-294 | Published online: 25 Sep 2008

References

  • Hoffmann D., Brunnemann K. D., Adams J. D., Hecht S. S. Formation and analysis of N-nitrosamines in tobacco products and their endogenous formation in consumers. N-Nitroso Compounds: Occurrence, Biological Effects and Relevance to Human Cancer, I. K. O'Neill, R. C. von Borstel, C. T. Miller, J. Long, H. Bartsch. International Agency for Research on Cancer, Lyon 1984; 743
  • Preussmann R., Stewart B. W. N-Nitroso carcinogens. Chemical Carcinogens, C. E. Searle, 1984; 643
  • Chen C. B., Hecht S. S., Hoffmann D. Metabolic α-hydroxylation of the tobacco-specific carcinogen N'-nitrosonomicotine. Cancer Res. 1978; 38: 3639
  • Hecht S. S., Young R., Chen C. B. Metabolism in the F344 rat of 4-(N-methyl-N-nitrosamino)-1-(3-pyridyl)-1-butanone, a tobacco speciñc carcinogen. Cancer Res. 1980; 40: 4144
  • Hecht S. S., Castonguay A., Chung F.-L., Hoffmann D. Carcinogenicity and metabolic activation of tobacco-specific nitrosamines: current status and future prospects. N-Nitroso Compounds: Occurrence, Biological Effects and Relevance to Human Cancer, I. K. O'Neill, R. C. von Borstel, C. T. Miller, J. Long, H. Bartsch. International Agency for Research on Cancer, Lyon 1984; 763
  • Hecht S. S., Spratt T. E., Trushin N. Evidence for 4-(3-pyridyl)-4-oxobutylation of DNA in F344 rats treated with the tobacco-specific nitrosamines 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone and N'-nitrosonomicotine. Carcinogenesis 1988; 9: 161
  • Morse M. A., Wang C.-H., Stoner G. D., Mandal S., Conran P. B., Anita S. G., Hecht S. S., Chung F.-L. Inhibition of 4-(methyuiitrosamino)-1-(3-pyridyl)-1-butanone-induced DNA adduct formation and tumorigenicity in the lung of F344 rats by dietary phenethyl isothiocyanate. Cancer Res. 1989; 49: 549
  • Castonguay A., Lin D., Stoner G. D., Radok P., Furuya K., Hecht S. S., Schut H. A. J., Klaunig J. E. Comparative carcinogenicity in A/J mice and metabolism by cultured mouse peripheral lung of N'-nitrosonornicotine, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone, and their analogues. Cancer Res. 1983; 43: 1223
  • Rrvenson A., Hoffmann D., Prokopcyk B., Amin S., Hecht S. S. Induction of lung and exocrine pancreas tumors in F344 rats by tobacco-specific and Areca-derived N-nitrosamines. Cancer Res. 1988; 48: 6912
  • Lai D. Y., Arcos J. C., Argus M. F. Factors influencing the microsome-and mitochondria-catalyzedin vitro binding of diethylnitrosamine and N-nitrosopiperidine to deoxyribonucleic acid. Biochem. Pharmacol. 1979; 28: 3545
  • Appel K. E., Ruf H. H., Mohr B., Schwarz M., Rickart R., Kunz W. Binding of nitrosamines to cytochrome P-450 of liver microsomes. Chem.-Biol. Interact 1979; 28: 17
  • Yang C. S., Yityoong Y. T., Koop D. R., Coon M. J. Metabolism of nitrosamines by purified liver cytochrome P-450 isozymes. Cancer Res. 1985; 45: 1140
  • Lee M., Ishlzaki H., Brady J. F., Yang C. S. Substrate specificity and alkyl group selectivity in the metabolism of N-nitrosodialkylamines. Cancer Res. 1989; 49: 1470
  • Johansson E. B., Tjälve H. The distribution of (14C)dimethylnitrosamine in mice: autoradiographic studies in mice with inhibited and non-inhibited dimethylnitrosamine metabolism and a comparison with the distribution of (14C)formaldehyde. Toxicol. Appl. Pharmacol. 1978; 45: 565
  • Johansson-Brittebo E., Tjälve H. Studies on the tissue-disposition and fate of N-(14C)ethyl-N-nitrosourea in mice. Toxicology 1979; 13: 275
  • Magee P. N. Toxic liver injury: the metabolism of dimethylnitrosamine. Biochem. J. 1956; 64: 767
  • Barnes J. M., Magee P. N. Some toxic properties of dimethylnitrosamine. Br. J. Ind. Med. 1954; 11: 167
  • Brittebo E. B., Löfberg B., Tjälve H. Sites of metabolism of N-nitrosodiethylamine in mice. Chem.-Biol. Interact 1981; 34: 209
  • Brittebo E. B., Lindgren A., Tjälve H. Foetal distribution and metabolism of N-nitrosodiethylamine in mice. Acta Pharmacol. Toxicol. 1981; 48: 355
  • Löfberg B., Tjälve H. The disposition and metabolism of N-nitrosodiethylamine in adult, infant and foetal tissues of the Syrian golden hamster. Acta Pharmacol. Toxicol. 1984; 54: 104
  • Brittebo E. B., Tjälve H. Tissue-specificity of N-nitrosodi-butylamine metabolism in Sprague-Dawley rats. Chem.-Biol. Interact 1982; 38: 231
  • Johansson-Brittebo E., Tjälve H. Studies on the distribution and metabolism of N-(14C)-nitrosopyrrolidine in mice. Chem.-Biol. Interact 1979; 25: 243
  • Löfberg B., Tjälve H. Tissue-specificity of N-nitrosomor-pholine metabolism in Sprague-Dawley rats. Food Chem. Toxicol. 1985; 23: 647
  • Löfberg B., Tjälve H. Autoradiography of (14C)-N-nitroso-diethanolamine in Sprague-Dawley rats. Cancer Lett. 1985; 31: 153
  • Kraft P. L., Tannenbaum S. R. Distribution of N-nitroso-methylbenzylamine evaluated by whole-body autoradiography. Cancer Res. 1980; 40: 1921
  • Hodgson R. M., Wiessler M., Kleihues P. Preferential methylation of target organ DNA by the oesophageal carcinogen N-nitrosomethylbenzylamine. Carcinogenesis 1980; 1: 861
  • Brittebo E., Tjälve H. Autoradiographic observations on the distribution and metabolism of N'-(14C)-nitrosonornicotine in mice. J. Cancer Res. Clin. Oncol. 1980; 98: 233
  • Brittebo E., Tjälve H. Formation of tissue-bound N'-nitro-sonornicotine metabolites by the target tissues of Sprague-Dawley and Fischer rats. Carcinogenesis 1981; 2: 959
  • Castonguay A., Tjälve H., Hecht S. S. Tissue-distribution of the tobacco-specific carcinogen 4-(meraylnitrosamino)-1-(3-pyridyl)-1-butanone and its metabolites in F344 rats. Cancer Res. 1983; 43: 630
  • Castonguay A., Tjälve H., Trusbin N., Hecht S. S. Perinatal metabolism of the tobacco-specific cacinogen 4-(methylnitro-samino)-1-(3-pyridyl)-1-butanone in C57BI mice. JNCI 1984; 72: 1117
  • Tjälve H., Castonguay A. The in vivo tissue disposition andin vitro target-tissue metabolism of the tobacco-specific carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in Syrian golden hamsters. Carcinogenesis 1983; 4: 1259
  • Castonguay A., Tjälve H., Tnishin N., d'Argy R., Sperber G. Metabolism and tissue-distribution of tobacco-specific N-nitrosamines in the marmoset monkey. (Callithrix jacchus), Carcinogenesis 1985; 11: 1543
  • Domeliöf L., Andersson M., Tjälve H., Veals S., Trushin S., Hecht S. S. Distribution and metabolism of N'-nitrosonomicotine in the miniature pig. Carcinogenesis 1987; 8: 1741
  • Shore P. A., Brodie B. B., Hogben C. A. M. The gastric secretion of drugs: a pH partition hypothesis. J. Pharmacol. Exp. Ther. 1957; 119: 361
  • Larsson B., Tjälve H. Studies on the mechanism of drug-binding to melanin. Biochem. Pharmacol. 1979; 28: 1181
  • Putney J. W., Jr., Borzelleca J. F. On the mechanism of14C-nicotine distribution in rat submaxillary gland in vitro. J. Pharmacol. Exp. Ther. 1971; 178: 180
  • Janzowski C., Jacob D., Hen I., Zankl H., Poole-Zobel B. L., Eisenbrand G. Investigations on organ-specific metabolism and genotoxic effects of the urinary bladder carcinogen N-nitrosobutyl-3-carboxypropylamine (BCPN) and its analogs N-nitro-sodibutylamine (NDBA) and N-nitrosobutyl-4-hydroxybutylamine (4-OH-NDBA). Toxicology 1989; 59: 195
  • Airoldi L., Magagnotti C., Bonfanti M., Fanelli R. Alpha-oxidative metabolism of the bladder carcinogens N-nitrosobutyl(4-hydroxybutyl)amine and N-nitrosobutyl(3-carboxypropyl)amine within the rat isolated bladder. Carcinogenesis 1990; 11: 1437
  • Löfberg B., Brittebo E. G., Tjälve H. Localization and binding of N'-nitrosonomicotine metabolites in the nasal region and in some other tissues of Sprague-Dawley rats. Cancer Res. 1982; 42: 2877
  • Tjälve H., Castonguay A. Localization of bound metabolites in the respiratory tissues and oesophagus by high-resolution microautoradiography in Fischer 344 rats treated with N'-nitrosonornicotine. Relevance of N-Nitroso Compounds to Human Cancers: Exposures and Mechanism, H. Bartsch, I. K. O'Neill, R. Schulte-Hermann. International Agency for Research on Cancer, Lyon 1987; 434
  • Hecht S. S., Reiss B., Lin D., Williams G. M. Metabolism of N'-nitrosonornicotine by cultured rat esophagus. Carcinogenesis 1982; 3: 453
  • Brittebo E. B., Castonguay A., Furuya K., Hecht S. S. Metabolism of tobacco-specific nitrosarnines by cultured rat nasal mucosa. Cancer Res. 1983; 43: 4343
  • Murphy S. E., Heiblum R., Trushin N. Comparative metabolism of N'-nitrosonomicotine and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone by cultured F344 rat oral tissue and esophagus. Cancer Res. 1990; 50: 4685
  • Belinsky S. A., White C. M., Trushin N., Hecht S. S. Cell specificity for the pulmonary metabolism of tobacco-specific nitrosarnines in the Fischer rat. Carcinogenesis 1989; 10: 2269
  • Hoffmann D., Raineri R., Hecht S. S., Maronpot R. R. Effects of N′-nitrosonomicotine and N′-nitrosoanabasine in rats. JNCI 1975; 55: 977
  • Singer G. M., Taylor H. W. Carcinogenicity of N'-nitrosonornicotine in Sprague-Dawley rats. JNCI 1976; 57: 1275
  • Hecht S. S., Chen C. B., Ohmori T., Hoffmann D. Comparative Carcinogenicity in F-344 rats of the tobacco-specific nitrosarnines N'-nitrosonomicotine and 4-(N-methyl-N-nitrosamino)-1-(3-pyridyl)-1-butanone. Cancer Res. 1980; 40: 298
  • Hecht S. S., Rivenson A., Braley J., Di Belio J., Adams J. D., Hoffmann D. Induction of oral cavity tumors in F344 rats by tobacco-specific nitrosarnines and snuff. Cancer Res. 1986; 46: 4162
  • Boyland E., Roe F. J. C., Gorrod J. W. Induction of pulmonary tumours by nitrosonornicotine. Nature 1964; 202: 1126
  • Hecht S. S., Chen C. B., Hirota N., Ornaf R. M., Tso T. C., Hoffmann D. Tobacco-specific nitrosarnines: formation from nicotinein vitro and during tobacco curing and Carcinogenicity in strain A mice. JNCI 1978; 60: 819
  • McCoy G. D., Katayama S., Young R., Wyatt M., Hecht S. S. Influence of chronic ethanol consumption on the metabolism and Carcinogenicity of tobacco-related carcinogens. N-Nitroso Compounds: Occurrence and Biological Effects, H. Bartsch, I. K. O'Neill, M. Castenaro, M. Okada. International Agency for Research on Cancer, Lyon 1982; 635
  • Hoffmann D., Castonguay A., Rivenson A., Hecht S. S. Comparative Carcinogenicity and metabolism of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone and N'-nitrosonornicotine in Syrian golden hamsters. Cancer Res. 1981; 41: 2386
  • Belinsky S. A., White C. M., Devereux T. R., Swenberg J. A., Anderson M. W. Cell selective alkylation of DNA in rat lung following low dose exposure to the tobacco specific carcinogen 4-(N-methyl-N-nitrosammo)-1-(3-pyridyl)-1-butanone. Cancer Res. 1987; 47: 1143
  • Belinsky S. A., Walker V. E., Maronpot R. R., Swenberg J. A., Anderson M. W. Molecular dosimetry of DNA adduct formation and eel! toxicity in rat nasal mucosa following exposure to the tobacco specific nitrosamine 4-(N-methyl-N-nitrosamino)-1-(3-pyridyl)-1-butanone and their relationship to induction of neoplasia. Cancer Res. 1987; 47: 6058
  • Tjälve H., Castonguay A., Rivenson A. Microautoradiographic localization of bound metabolites in the nasal cavities of F344 rats treated with the tobacco-specific carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone. JNCI 1985; 74: 185
  • Castonguay A., Foiles P. G., Trushin N., Hecht S. S. A study of DNA methylation by tobacco-specific N-nitrosamines. Environ. Health Perspect 1985; 62: 197
  • Hecht S. S., Trushin N., Castonguay A., Rivenson A. Comparative carcinogenicity and DNA methylation in F344 rats by 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone and N-nitrosodimethylamine. Cancer Res. 1986; 46: 498
  • Belinsky S. A., White C. M., Boucheron J. A., Richardson F. C., Swenberg J. A., Anderson M. Accumulation and persistence of DNA adducts in respiratory tissue of rats following multiple administrations of the tobacco specific carcinogen 4-(N-methyl-N-nitrosamino)-1-(3-pyridyl)-1-butanone. Cancer Res. 1986; 46: 1280
  • Hecht S. S., Hoffmann D. Tobacco-specific nitrosamines, an important group of carcinogens in tobacco and tobacco smoke. Car-anagenesis 1988; 9: 875
  • Devereux T. R., Anderson M. W., Belinsky S. A. Factors regulating activation and DNA alkylation by 4-(N-methyl-N-nitrosamino)-1-(3-pyridyl)-1-butanone and nitrosodimethylamine in rat lung and isolated lung cells, and their relationship to carcinogenicity. Cancer Res. 1988; 48: 4215
  • Prokopczyk G., Adams J. D., LaVoie E. J., Hoffmann D. Effect of snuff and nicotine on DNA methylation by 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone. Carcinogenesis 1987; 8: 1395
  • van Ben them J., Wilmer J. W. G. M., Winterwerp H. H. K., Leeman W. R., Scherer E., den Engelse L. Immunocy-tochemical study of formation and repair of NNK-induced DNA adducts in nasal epithelium. Nasal Carcinogenesis in Rodents: Relevance to Human Health Risk, V. J. Feron, M. C. Bosland. Pudoc, WageningenThe Netherlands 1989; 152
  • van Benthem J., Wilmer J. W. G.M., Leeman W. R., Winterwerp H. H. K., den Engelse L., Scherer E. Immuno-cytochemical study of DNA adduct formation by the tobacco-specific nitrosamine 4-(N-methyl-N-m'trosamino)-1-(3-pyridyl)-1-butanone (NNK) in rat and hamster. Tobacco and Cancer: Perspectives in Preventive Research, A. P. Maskens, R. Molimard, R. Preussmann, J. W. Wolmer. Excerpta Medica, Amsterdam 1989; 49
  • Belinsky S. A., Foley J. F., White C. M., Anderson M. W., Maronpot R. R. Dose-response relationship between O6-meth-ylguanine formation in Clara cells and induction of pulmonary neoplasia in the rat by 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone. Cancer Res. 1990; 50: 3772
  • Belinsky S. A., Devereux T. R., Maronpot R. R., Stoner G. D., Anderson M. W. Relationship between the formation of promutagenic adducts and the activation of the K-ras protooncogene in lung tumors from A/J mice treated with nitrosamines. Cancer Res. 1989; 49: 5305
  • Hecht S. S., Morse M. A., Amin S., Stoner G. D., Jordan K. G., Choi C.-I., Chung F.-L. Rapid single-dose model for lung tumor induction in A/J mice by 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone and the effect of diet. Carcinogenesis 1989; 10: 1901
  • Anderson L. M., Hecht S. S., Dixon D. E., Dove L. F., Kovatch R. M., Amin S., Hoffmann D., Rice J. M. Evaluation of the transplacental tumorigenicity of the tobacco-specific carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in mice. Cancer Res. 1989; 49: 3770
  • LaVoie E. J., Prokopczyk G., Rigotty J., Czech A., Rivenson A., Adams J. D. Tumorigenic activity of the tobacco-specific nitrosamines 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK), 4-(methylnitrosamino)-4-(3-pyridyl)-1-butanol (iso-NNAL) and N'-nitrosonomicotine (NNN) on topical application to SENCAR mice. Cancer Lett. 1987; 37: 277
  • Alaoui-Jamal M. A., Massey T. E., Douglas A., Rossignol G., Castonguay A. In vitro metabolism of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone by lung cells isolated from Syrian golden hamster. Cancer Lett. 1990; 52: 49
  • Castonguay A., Allaire L., Charest M., Rossignol G., Boutet M. Metabolism of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone by hamster respiratory tissues cultured with ellagic acid. Cancer Lett. 1989; 46: 93
  • Hecht S. S., Adams J. D., Numoto S., Hoffmann D. Induction of respiratory tract tumors in Syrian golden hamsters by a single dose of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) and the effect of inhalation. Carcinogenesis 1983; 4: 1287
  • Schüller H. M., Witschi H.-P., Nylen E., Joshi P. A., Correa E., Becker K. L. Pathobiology of lung tumors induced in hamsters by 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone and the modulating effect of hyperoxia. Cancer Res. 1990; 50: 1960
  • Brittebo E., Lofberg B., Tjälve H. Extrahepatic sites of metabolism of N-nitrosopyrrolidine in mice and rats. Xenobiotica 1981; 11: 619
  • Hecht S. S., Chen C.-H. B., McCoy G. D., Hoffmann D. α-Hydroxylation of N-mtrosopyrrolidine and N'-nitrosonorni-cotine by human liver microsomes. Cancer Lett. 1979; 8: 35
  • Lijinsky W., Taylor H. W. The effect of substituents on the carcinogenicity of N-nitrosopyrrolidine in Sprague-Dawley rats. Cancer Res. 1976; 36: 1988
  • Greenblatt M., Lijinsky W. Failure to induce tumors in Swiss mice after concurrent administration of amino acids and sodium nitrite. JNCI 1972; 48: 1389
  • Some N-nitroso compounds. IARC Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. International Agency for Research on Cancer, Lyon 1980; Vol. 17
  • Herrold K. M., Dunham L. J. Induction of tumors in the Syrian hamster with diethylnitrosamine (N-nitrosodiethylamine). Cancer Res. 1963; 23: 773
  • Lofberg B., Tjälve H. Perinatal metabolism of N-nitrosodibutylamine in Syrian golden hamsters. Cancer Lett. 1986; 31: 153
  • Rogers A. E., Sanchez O., Feinsod F. M., Newberne P. M. Dietary enhancement of nitrosamine Carcinogenesis. Cancer Res. 1974; 34: 96
  • Hecht S. S., Young R. Metabolic α-hydroxylation of N-nitrosomorpholine and 3,3,5,5-tetradeutero-N-nitrosomorpholine in the F344 rat. Cancer Res. 1981; 41: 5039
  • Druckrey H., Preussmann R., Ivankovic S., Schmähl D. Organotrope carcinogene Wirkungen bei 65 verschiedenen N-nitroso-Verbindungen an BD-Ratten. Z. Krebsforsch. 1967; 69: 103
  • Garcia H., Lyinsky W. Tumorigenicity of five cyclic nitrosamines in MRC rats. Z. Krebsforsch. 1972; 77: 257
  • Lyinsky W., Kovatch R. M., Riggs C. W., Walters P. T. Dose response study with N-nitrosomorpholine in drinking water of F-344 rats. Cancer Res. 1988; 48: 2089
  • Preussmann R., Habs H., Schmähl D. Carcinogenicity of N-nitrosodiethanolamine in rats at five different dose levels. Cancer Res. 1982; 42: 5167
  • Denkel E., Sterzel W., Eisenbrand G. In vivo activation of N-nitrosodiethanolamine and other N-nitroso-2-hydroxyalkylamines by alcohol dehydrogenase and sulfotransferase. The Relevance of N-Nitroso Compounds to Human Cancer: Exposures and Mechanisms, H. Bartsch, I. K. O'Neill, R. Schulte-Hermann. International Agency for Research on Cancer, Lyon 1987; 83
  • Harris C. C., Autrup H., Stoner G. D., Trump B. F., Hillman E., Schafer P. W., Jeffrey A. M. Metabolism of benzo(a)pyrene, N-nitrosodimethylamine, and N-nitrosopyrrolidine and identification of the major carcinogen-DNA adducts formed in cultured human esophagus. Cancer Res. 1979; 39: 4401
  • Yoo J.-S. H., Guengerich F. P., Yang C. S. Metabolism of N-nitrosodialkylamines by human liver microsomes. Cancer Res. 1988; 88: 1499
  • Castonguay A., Stoner G. D., Schut H. A., Hecht S. S. Metabolism of tobacco-specific N-nitrosamines by cultured human tissues. Proc. Natl Acad. Sci. U.S.A. 1990; 80: 694
  • Tjälve H., Löfberg B. Extrahepatic sites of metabolism of carbon tetrachloride in rats. Chem.-Biol. Interact 1983; 46: 299
  • Löfberg B., Tjälve H. Tracing tissues with chloroform-metabolizing capacity in rats. Toxicology 1986; 39: 13
  • Ghantous H., Löfberg B., Tjälve H., Danielsson B. R.G., Dencker L. Extrahepatic sites of metabolism of halothane in the rat. Toxicology 1988; 62: 135
  • Brittebo E. B., Kowalski B., Ghantous H., Brandt I. Epithelial binding of 1,2-dichloroethane in mice. Toxicology 1989; 56: 35
  • Brittebo E. B., Tjälve H. Metabolism of N-nitrosamines by the nasal mucosa. Nasal Tumors in Animals and Man: Experimental Nasal Carcinogenesis, G. Reznik, S. F. Stinson. CRC Press, Inc., Boca Raton, FL 1983; Vol. 3: 233
  • Dahi A. R., Hadley W. M., Hahn F. F., Benson J. M., McClellan R. O. Cytochrome P-450-dependent monooxygenases in the olfactory epithelium of dogs: possible role in tumourigenicity. Science 1982; 216: 57
  • Reed C. J., Lock E. A., De Matteis F. Olfactory cytochrome P-450: studies with suicide substrates of the haemoprotein. Biochem. J. 1988; 253: 569
  • Ding X., Coon M. J. Purification and characterization of two unique forms of cytochrome P-450 from rabbit nasal microsomes. Biochemistry 1988; 27: 8330
  • Nef P., Larabee T. M., Kagtanoto K., Meyer U. A. Olfactory-specific cytochrome P-450 (P-450olfl; IIG1): gene structure and developmental regulation. J. Biol. Chem. 1990; 265: 2903
  • Voigt J. M., Guengerich P., Baron J. Localization of a cytochrome P-450 isozyme (cytochrome P-450 PB-B) and NADPH-cytochrome P-450 reductase in rat nasal mucosa. Cancer Lett. 1985; 27: 241
  • Jones K. G., Holland J. F., Foureman G. L., Bend J. R., Fonts J. R. Xenobiotic metabolism in Clara cells and alveolar type II cells isolated from lungs of rats treated with β-naphthoflavone. J. Pharmacol. Exp. Ther. 1983; 225: 316
  • Domin B. A., Devereux T. R., Philpot R. M. The cytochrome P-450 monooxygenase system of rabbit lung: enzyme components, activities, and induction in the nonciliated bronchiolar epithelial (Clara) cell, alveolar type II cell, and alveolar macrophage. Mol. Pharmacol. 1986; 30: 296
  • Baron J., Voigt J. M., Whitter T. B., Kawabata T. T., Knapp S. A., Guengerich F. P., Jakoby W. B. Identification of intratissue sites for xenobiotic activation and detoxication. Biological Reactive Intermediates III, Mechanisms of Action in Animal Models and Human Disease, J. J. Kocsis, D. J. Jollow, C. M. Witmer, J. O. Nelson, R. Snyder. Plenum Press, New York 1986; 119
  • Azzopardi A., Thurlbeck W. M. Oxidative enzyme pattern of the bronchial mucous glands. Am. Rev. Resp. Dis. 1968; 97: 1038
  • Reznik-Schüller H. Pathogenesis of diethylnitrosamine-induced tumours in the trachea of the Syrian golden hamster. Pathol. Res. Pract. 1980; 168: 185
  • Reznik-Schüller H. M., Hague B. F., Jr. Autoradiographic study of the distribution of bound radioactivity in the respiratory tract of Syrian hamsters given N-3H/nitrosodiethylamine. Cancer Res. 1981; 41: 2147
  • Lijinsky W. Structure-activity relations in carcinogenesis by N-nitroso compounds. Cancer Metastatis Rev. 1987; 6: 301
  • Labuc G. E., Archer M. C. Esophageal and hepatic microsomal metabolism of N'-nitrosomethylbenzylamine and N-nitrosodimethylamine in the rat. Cancer Res. 1982; 42: 3181
  • Mirvish S. S., Ji C., Rosinsky S. Hydroxy metabolites of methyl-n-amylnitrosamine produced by esophagus, stomach, liver, and other tissues of the neonatal to adult rat and hamster. Cancer Res. 1988; 48: 5663
  • Koenigsmann M., Schmerold I., Jeltsch W., Ludeke B., Kleihues P., Wiessler M. Organ and cell specificity of DNA methylation by N-nitrosomethylamylamine in rats. Cancer Res. 1988; 48: 5482
  • Wiestler O. D., von Deimling A., von Hofe E., Schmerold I., Wiestler E., Kleihues P. Interorgan shift of nitrosamine metabolism by dietary ethanol. Arch. Toxicol. 1987; 53, Suppl. 11
  • Van Benthem J., Wild C. P., Vermuelen E., Winterwerp H. H. K., Den Engelse L., Scherer E. Immunocytochemical localization of DNA adducts in rat tissues following treatment with N-nitrosomethylbenzylamine. Methods for Detecting DNA Damaging Agents in Humans: Applications in Cancer Epidemiology and Prevention, H. Bartsch, K. Hemminki, I. K. O'Neill. International Agency for Research on Cancer, Lyon 1988; 102
  • Endou H. Cytochrome P-450 monooxygenase system in the rabbit kidney: its intranephron localization and its induction. Jpn. J. Pharmacol 1983; 33: 423
  • Mangino M. M., Scarpelli D. G., Kokkinakis D. M. Metabolism and activation of the pancreatic carcinogen N-nitrosobis(2-oxopropyl)amine by isolated hepatocytes and pancreatic cells of the Syrian hamster. Carcinogenesis 1990; 11: 625
  • Bax J., Schippers-GUIisen C., Woutersen R. A., Scherer E. Immunocytochemical detection of O6-methylguanine after in vivo application of N-nitrosobis(2-oxopropyl)amine. Proc. Am. Assoc. Cancer Res. 1987; 28: 126
  • Nebert D. W., Adesnik M., Coon M. J., Estabrook R. W., Gonzalez F. J., Guengerich F. P., Gunsahis I. C., Johnson E. F., Kemper B., Levin W., Phillips I. R., Sato R., Waterman M. R. The P450 gene superfamily: recommended nomenclature. DNA 1987; 6: 1
  • Ayrton A. D., Smith J. N., Ioannides C. Bioactivation of N-nitrosopiperidine to mutagens: role of hepatic cytochrome P-450 proteins and contribution of cytosolic fraction. Carcinogenesis 1987; 8: 1691
  • Mohr U., Reznik-Schüller H., Reznik G., Hilfrich J. Transplacental effects of diethylnitrosamine in Syrian hamsters related to different days of administration during pregnancy. JNCI 1975; 55: 681
  • Althoff J., Pour R., Grandjean C., Eagan M. Transpla-cental effects of mtrosamines in Syrian hamsters. I. Dibutylnitrosamine and nitrosohexamethyleneimine. Z. Krebsforsch. 1976; 86: 69
  • Mohr U., Althoff J. Carcinogenic activity of aliphatic nitrosamines via mother's milk in the offspring of Syrian golden hamsters. Proc. Soc. Exp Biol. Med. 1971; 136: 1007
  • Mohr U., Althoff J., Emminger A., Bresch H., Splelhoff R. Effects of nitrosammes in nursing Syrian golden hamsters and their offspring. Z. Krebsforsch. 1972; 78: 73
  • Mohr U., Atthoff J. Die diplacentare Wirkung des Cancer-ogens Diäihylnitrosamin bei der Maus. Z. Krebsforsch. 1965; 67: 152
  • Johansson-Brittebo E., Tjälve H. Studies on the distribution and metabolism of14C-dimethylnitrosamine in foetal and young mice. Acta Pharmacol. Toxicol. 1979; 45: 73
  • Anderson L. M., Hagiwara A., Kovatch R. M., Rehm S., Rice J. M. Transplacental initiation of liver, lung, neurogenic, and connective tissue tumors by N-nitroso compounds in mice. Fund. Appl. Toxicol. 1989; 12: 604
  • Tjälve H., Löfberg B., Castonguay A., Trushln N., Hecht S. S. Perinatal disposition and metabolism in mice and hamsters of some N-nitrosamines present in tobacco and tobacco smoke. Mechanisms in Tobacco Carcinogenesis, D. Hoffmann, C. C. Harris. Cold Spring Harbor Laboratory, Cold Spring Harbor, New York 1986; 179, Banbury Report 23
  • Castonguay A., Rivenson A., Tjälve H. Cancérogénèse de la fumée de tabac: une etude chez le hamster doré. Interface 1985; 6: 16
  • Rossignol G., Alaoui-Jamall M. A., Castonguay A., Schüller H. M. Metabolism and DNA damage induced by 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in fetal tissues of the Syrian golden hamster. Cancer Res. 1989; 49: 5671
  • Correa E., Joshi P. A., Castonguay A., Schuller H. M. The tobacco-specific nitrosamine 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone is an active transplacental carcinogen in Syrian golden hamsters. Cancer Res. 1990; 50: 3435
  • Schuller H. M., Cote R. Regulation of cell proliferation of β-adrenergic receptors in a human lung adenocarcinoma cell line. Carcinogenesis 1989; 10: 1753
  • Schuller H. M. Cell type specific, receptor-mediated modulation of growth kinetics in human lung cancer cell lines by nicotine and tobacco-relatednitrosamines. Biochem. Pharmacol. 1989; 38: 3439
  • Richardson F. C., Dyroff M. C., Boucheron J. A., Swenberg J. A. Differential repair of O4-alkylthymidine following exposure to methylating and ethylating hepatocarcinogens. Carcinogenesis 1985; 6: 625
  • Suzuki E., Osabe M., Okada M., Ishlzaka T., Suzuki T. Urinary metabolites of N-nitrosodibutylamine in the rat: identification of N-aceryl-S-butyl-L-cystein derivatives. The Relevance of N-Nitroso Compounds to Human Cancer: Exposures and Mechanisms, H. Bartsch, I. K. O'Neill, R. Schulte-Hermann. International Agency for Research on Cancer, Lyon 1987; 153
  • Wiessler M., Rossnagel G. α-Glucuronides of N-nitroso-methylbenzylamine. The Relevance of N-Nitroso Compounds to Human Cancer: Exposures and Mechanisms, H. Bartsch, I. K. O'Neill, R. Schulte-Hermann. International Agency for Research on Cancer, Lyon 1987; 170
  • Wiench K., Schroth P., Frei E., Wiessler M. Glucuron-idation of N-nitrosodiethylamine in rat hepatocytes. J. Cancer Res, Clin. Oncol., 116(Suppl.)90, 190, [Part 1])
  • Morse M. A., Ekiind K. I., Amto S. G., Hecht S. S., Chung F.-L. Effects of alkyl chain length on the inhibition of NNK-induced lung neoplasia in A/J mice by arylalkyl isothiocyanates. Carcinogenesis 1989; 10: 1757
  • Barch D. H., Fox C. C. Selective inhibition of methylbenzylnitrosamine-induced formation of esophageal O6-methylguanine by dietary ellagic acid in rats. Cancer Res. 1988; 48: 7088

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.