Mechanisms of lung tumorigenesis by ethyl carbamate and vinyl carbamate

References

• Aldridge, W. N. (1953). Serum esterases. I. Two types of esterases (A and B) hydrolyzing p-nitrophenylacetate propionate and butyrate and a method of their determination. Biochem. J. 53:110–117.
   PubMed Web of Science ®Google Scholar
• Barbin, A., Bartsch, H. (1986). Mutagenic and promutagenic properties of DNA adducts formed by vinyl chloride metabolites. In: Singer, B., Bartsch, A. ( Eds.), The role of cyclic nucleic acid adducts in carcinogenesis and mutagenesis (pp 345–358). Lyon, France: IARC Scientific Publications No. 70, International Agency for Research on Cancer.
   Google Scholar
• Barbin, A. (2000). Etheno-adduct forming chemicals: from mutagenicity testing to tumor mutation spectra. Mutat Res 462:462–455.
   Google Scholar
• Bartsch, H., Barbin, A., Marion, M. J., Nair, J., Guichard, Y. (1994). Formation, detection, and role in carcinogenesis of ethenobases in DNA. Drug Metab Rev 26:349–371.
   PubMed Web of Science ®Google Scholar
• Basu, A. K., Wood, M. L., Neidernhofer, L. J., Ramos, L. A., Essigmann, J. M. (1993). Mutagenic and genotoxic effects of three vinyl chloride-induced DNA lesions: 1,N6-ethenoadenine, 3,N4-ethenocytosine, and 4-amino-5-(imidazol-2-yl)imidazole. Biochemistry 32:12793–12801.
   PubMed Web of Science ®Google Scholar
• Black, G. P., Collins, K. S., Blacquiere, D. P., Forkert, P. G. (2006). Formation of N-alkylprotoporphyrin IX from metabolism of diallyl sulfone in lung and liver. Drug Metab Dispos 34:895–900.
   PubMed Web of Science ®Google Scholar
• Boyland, E., Rhoden, E. (1949). The distribution of urethane in animal tissue, as determined by a microdiffusion method, and the effect of urethane treatment on enzymes. Biochem J 44:528–531.
   PubMed Web of Science ®Google Scholar
• Bryan, C. E., Skipper, H. E., White, L. (1949). Carbamates in the chemotherapy of leukemic. IV. The distribution of radioactivity in tissues of mice following injection of carbonyl-labeled urethane. J Biol Chem 177:941–950.
   PubMed Web of Science ®Google Scholar
• Cariello, N. F., Piegorsch, W. W., Adams, W. T., Skopek, T. R. (1994). Computer program for the analysis of mutational spectra: application to p53 mutations. Carcinogenesis 15:2281–2285.
   PubMed Web of Science ®Google Scholar
• Cosentino, L., Heddle, J. A. (1996). A test for neutrality of mutations of the lacZ transgene. Environ Mol Mutagen 28:313–316.
   PubMed Web of Science ®Google Scholar
• Dahl, G. A., Miller, E. C., Miller, J. A. (1980). Comparative carcinogenicities and mutagenicities of vinyl carbamate, ethyl carbamate, and ethyl N-hydroxycarbamate. Cancer Res 40:1194–1203.
   PubMed Web of Science ®Google Scholar
• Dahl, G. A., Miller, J. A., Miller, E. C. (1978). Vinyl carbamate as a promutagen and a more carcinogenic analog of ethyl carbamate. Cancer Res 38:3793–3804.
   PubMed Web of Science ®Google Scholar
• Der, C. J., Pan, B. T., Cooper, G. M. (1986). rasH mutants deficient in GTP binding. Mol Cell Biol 6:3291–3294.
   PubMed Web of Science ®Google Scholar
• Dixon, D., Horton, J., Haseman, J. K., Talley, F., Greenwell, A., Nettesheim, P., et al. (1991). Histomorphology and ultrastructure of spontaneous pulmonary neoplasms in strain A mice. Exp Lung Res 17: 131–155.
   PubMed Web of Science ®Google Scholar
• Douglas, G. R., Jiao, J., Gingerich, J. D., Soper, L. M., Gossen, J. A. (1996). Temporal and molecular characteristics of lacZ mutations in somatic transgenic mice. Environ Mol Mutagen 28:317–324.
   PubMed Web of Science ®Google Scholar
• Fernando, R. C., Nair, J., Barbin, A., Miller, J. A., Bartsch, H. (1996). Detection of 1,N6-ethenodeoxyadenosine and 3,N4-ethenocytidine by immunoaffinity/32P-postlabelling in liver and lung DNA of mice treated with ethyl carbamate (urethane) or its metabolites. Carcinogenesis 17:1711–1718.
   PubMed Web of Science ®Google Scholar
• Forkert, P. G. (1995). CYP2E1 is preferentially expressed in Clara cells of murine lung: localization by in situ hybridization and immunohistochemical methods. Am J Resp Cell Mol Biol 12:589–596.
   PubMed Web of Science ®Google Scholar
• Forkert, P. G., Kaufmann, M., Black, G., Bowers, R., Chen, H., Collins, K., et al. (2007). Oxidation of vinyl carbamate and formation of 1,N6-ethenodeoxyadenosine in murine lung. Drug Metab Dispos 35:713–720.
   PubMed Web of Science ®Google Scholar
• Forkert, P. G, Lee, R. P. (1997). Metabolism of ethyl carbamate by pulmonary cytochrome P450 and carboxylesterase isozymes: involvement of CYP2E1 and hydrolase A. Toxicol Appl Pharmacol 146:245–254.
   PubMed Web of Science ®Google Scholar
• Forkert, P. G., Lee, R. P., Dowsley, T. F., Hong, J.-Y., Ulreich, J. B. (1996). Protection from 1,1-dichloroethylene-induced Clara cell injury by diallyl sulfone, a derivative of garlic. J Pharmacol Exp Ther 277:1665–1671.
   PubMed Web of Science ®Google Scholar
• Forkert, P. G, Lee, R. P., Reid, K. (2001). Involvement of CYP2E1 and carboxylesterase enzymes in vinyl carbamate metabolism in human lung microsomes. Drug Metab Dispos 29:258–263.
   PubMed Web of Science ®Google Scholar
• Forkert, P. G., Premdas, P. D., Bowers, R. J. (2000). Epoxide formation from diallyl sulfone is associated with CYP2E1 inactivation in murine and human lungs. Am J Resp Cell Mol Biol 23:687–695.
   PubMed Web of Science ®Google Scholar
• Ghanayem, B. I. (2007). Inhibition of urethane-induced carcinogenicity in Cyp2e1-/- in comparison to Cyp2e1+/+ mice. Toxicol Sci 95:331–339.
   PubMed Web of Science ®Google Scholar
• Gossen, J. A., de Leeuw, W. J., Tan, C. H., Zwarthoff, E. C., Berends, F., Lohman, P. H., et al. (1989). Efficient rescue of integrated shuttle vectors from transgenic mice: a model for studying mutations in vivo. Proc Natl Acad Sci U S A 86:7971–7975.
   PubMed Web of Science ®Google Scholar
• Guengerich, F. P., Kim, D. H. (1991). Enzymatic oxidation of ethyl carbamate and its role as an intermediate in the formation of 1,N6-ethenoadenosine. Chem Res Toxicol 4:413–421.
   PubMed Web of Science ®Google Scholar
• Guengerich, F. P., Kim, D. H., Iwasaki, M. (1991). Role of human cytochrome P450IIE1 in the oxidation of many low molecular weight cancer suspects. Chem Res Toxicol 4:168–179.
   PubMed Web of Science ®Google Scholar
• Hakkola, J., Pasanen, R., Purkunen, R., Saarikoski, S., Pelkonen, O., Maenpaa, J., et al. (1994). Expression of xenobiotic-metabolizing cytochrome P-450 forms in human adult and fetal liver. Biochem Pharmacol 48:59–64.
   PubMed Web of Science ®Google Scholar
• Harbach, P. R., Zimmer, D. M., Filipunas, A. L., Mattes, W. B., Aaron, C. S. (1999). Spontaneous mutation spectrum at the lambda cII locus in liver, lung, and spleen tissue of Big Blue® transgenic mice. Environ Mol Mutagen 33:132–143.
   PubMed Web of Science ®Google Scholar
• Heddle, J. A., Martus, H. J., Douglas, G. R. (2003). Treatment and sampling protocols for transgenic mutation assays. Environ Mol Mutagen 41:1–6.
   PubMed Web of Science ®Google Scholar
• Heddle, J. A. (1999). Mutant manifestation: the time factor in somatic mutagenesis. Mutagenesis 14:1–3.
   PubMed Web of Science ®Google Scholar
• Hernandez, L. G., Forkert, P. G. (2007a). In vivo mutagenicity of vinyl carbamate and ethyl carbamate in lung and small intestine of F1 (Big Blue® × A/J) transgenic mice. Int J Cancer 120:1426–1433.
   PubMed Web of Science ®Google Scholar
• Hernandez, L. G., Forkert, P. G. (2007b). Inhibition of vinyl carbamate-induced mutagenicity and clastogenicity by the garlic constituent diallyl sulfone in F1 (Big Blue® × A/J) transgenic mice. Carcinogenesis 28:1824–1830.
   PubMed Web of Science ®Google Scholar
• Heymann, E., Junge, W., Krisch, K. (1972). Reaction with phenylmethylsulfonyl fluoride and detection of isoenzymes. Hoppe-Seyler′s Z Physiol Chem 353:576–588.
   PubMedGoogle Scholar
• Hoffler, U., El-Masri, H. A., Ghanayem, B. I. (2003). Cytochrome P450 2E1 (CYP2E1) is the principal enzyme responsible for urethane metabolism: comparative studies using CYP2E1-null and wild-type mice. J Pharmacol Exp Ther 305:557–564.
   PubMed Web of Science ®Google Scholar
• IARC. (2007). Alcoholic beverage consumption and ethyl carbamate (urethane), vol 96. Lyon, France: IARC.
   Google Scholar
• Jakubczak, J. L., Merlino, G., French, J. E., Muller, W. J., Paul, B., Adhya, S., et al. (1996). Analysis of genetic instability during mammary tumor progression using a novel-based assay for in vivo mutation in the bacteriophage λ transgene target. Proc Natl Acad Sci U S A 93:9073–9078.
   PubMed Web of Science ®Google Scholar
• Jackson, A. L., Loeb, L. A. (2001). The contribution of endogenous sources of DNA damage to the multiple mutations in cancer. Mutat Res 477:7–21.
   PubMed Web of Science ®Google Scholar
• Kaufman, S. L., Alexander, L., Sass, L. (1979). Histologic and ultrastructural features of the Clara cell adenoma of the mouse lung. Lab Invest 40:708–716.
   PubMed Web of Science ®Google Scholar
• Kaye, A. M. (1960). A study of the relationship between the rate of ethyl carbamate (urethan) catabolism and urethan carcinogenesis. Cancer Res 20:237–241.
   PubMed Web of Science ®Google Scholar
• Kemper, R. A., Myers, S. R., Hurst, H. E. (1995). Detoxification of vinyl carbamate epoxide by glutathione: evidence for participation of glutathione S-transferases in metabolism of ethyl carbamate. Toxicol Appl Pharmacol 135:110–118.
   PubMed Web of Science ®Google Scholar
• Kitz, R., Wilson, I. B. (1962). Esters of methanesulfonic acid as irreversible inhibitors of acetylcholinesterase. J Biol Chem 237:3245–3249.
   PubMed Web of Science ®Google Scholar
• Kohler, S. W., Provost, G. S., Fieck, A., Kretz, P. L., Bullock, W. O., Sorge, J. A., et al. (1991). Spectra of spontaneous and mutagen-induced mutations in the lacI gene in transgenic mice. Proc Natl Acad Sci U S A 88:7958–7962.
   PubMed Web of Science ®Google Scholar
• Lee, R. P., Forkert, P. G. (1999). Inactivation of cytochrome P-450 (CYP2E1) and carboxylesterase (hydrolase A) enzymes by vinyl carbamate in murine pulmonary microsomes. Drug Metab Dispos 27:233–239.
   PubMed Web of Science ®Google Scholar
• Leithauser, M. T., Liem, A., Stewart, B. C., Miller, E. C., Miller, J. A. (1990). 1,N6-ethenoadenosine formation, mutagenicity, and murine tumor as indicators of the generation of an electrophilic epoxide metabolite of the closely related carcinogens ethyl carbamate (urethane) and vinyl carbamate. Carcinogenesis 11:463–473.
   PubMed Web of Science ®Google Scholar
• Malkinson, A. M. (1991). Genetic studies on lung tumor susceptibility and histogenesis in mice. Environ Health Perspect 93:149–159.
   PubMed Web of Science ®Google Scholar
• Massey, T. E., Devereux, T. R., Maronpot, R. R., Foley, J. F., Anderson, M. W. (1995). High frequency of K-ras mutations in spontaneous and vinyl carbamate-induced lung tumors of relatively resistant B6CF1 (C57BL/6J × BALB/cJ) mice. Carcinogenesis 16:1065–1069.
   PubMed Web of Science ®Google Scholar
• McCracken, N. W., Blain, P. G., Williams, F. M. (1993). Nature and role of xenobiotic metabolizing esterases in rat liver, lung, skin, and blood. Biochem Pharmacol 45: 31–36.
   PubMed Web of Science ®Google Scholar
• Miller, J. A. (1991). The need for epidemiological studies of the medical exposures of Japanese patients to the carcinogen, ethyl carbamate (urethane), from 1950 to 1975. Jpn J Cancer Res 82:1323–1324.
   PubMedGoogle Scholar
• Miller, J. A. Miller, E. C. (1983). The metabolic activation and nucleic acid adducts of naturally occurring carcinogens: recent results with ethyl carbamate and the spice flavors, safrole and estragole. Br J Cancer 48:1–15.
   PubMed Web of Science ®Google Scholar
• Mirvish, S. S. (1968). The carcinogenic action and metabolism of urethan and N-hydroxyurethan. Adv Cancer Res 21:1–42.
   Google Scholar
• Mirvish, S. S., Kaye, A. M. (1964). The catabolism of urethane by mouse-liver homogenates. Biochem Biophys Acta 82:397–402.
   PubMed Web of Science ®Google Scholar
• Monteiro, F. F., Bisson, L. F. (1991). Amino acid utilization and urea formation during vinification fermentations. Am J Enol Vitic 42:199–208.
   Web of Science ®Google Scholar
• Morgan, E. W., Yan, B., Greenway, D., Petersen, D. R., Parkinson, A. (1994a). Purification and characterization of two rat liver microsomal carboxylesterases (hydrolase A and B). Arch Biochem Biophys 315:495–512.
   PubMed Web of Science ®Google Scholar
• Morgan, E. W., Yan, B., Greenway, D., Parkinson, A. (1994b). Regulation of two rat liver microsomal carboxylesterase isozymes: species differences, tissue distribution, and the effects of age, sex, and xenobiotic treatment of rats. Arch Biochem Biophys 315:513–526.
   PubMed Web of Science ®Google Scholar
• Moriya, M., Zhang, W., Johnson, F., Grollman, A. P. (1994). Mutagenic potency of exocyclic DNA adducts: marked differences between Escherichia coli and simian kidney cells. Proc Natl Acad Sci U S A 91:11899–11903.
   PubMed Web of Science ®Google Scholar
• Mostofi, F. K., Larsen, C. D. (1951). The histogenesis of pulmonary tumors induced in strain A mice by urethan. J Natl Cancer Inst 11:1187–1221.
   PubMed Web of Science ®Google Scholar
• Nettleship, A., Henshaw, P. S., Meyer, H. L. (1943). Induction of pulmonary tumors in mice with ethyl carbamate (urethane). J Natl Cancer 4:309–319.
   Google Scholar
• Nomier, A. A., Ioannou, Y. M., Sanders, J. M., Matthews, H. B. (1989). Comparative metabolism and disposition of ethyl carbamate (urethan) in male Fischer 344 rats and male B6C3F1 mice. Toxicol Appl Pharmacol 97:203–215.
   PubMed Web of Science ®Google Scholar
• Nomura, T. (1975). Urethane (ethyl carbamate) as a co-solvent of drugs commonly used parenterally in humans. Cancer Res 35:2895–2899.
   PubMed Web of Science ®Google Scholar
• Nuzum, E. O., Malkinson, A. M., Beer, D. G. (1990). Specific Ki-ras codon 61 mutations may determine the development of urethan-induced mouse lung adenomas or adenocarcinomas. Mol Carcinog 3:287–295.
   PubMed Web of Science ®Google Scholar
• Page, D. A., Carlson, G. P. (1994). The effect of pyridine on the in vitro and in vivo metabolism of ethyl carbamate (urethane) by rat and mouse. Carcinogenesis 15:2177–2181.
   PubMed Web of Science ®Google Scholar
• Pandya, G. A., Moriya, M. (1996). 1,N6-ethenoadenosine, a DNA adduct highly mutagenic in mammalian cells. J Agric Food Chem 24:323–328.
   Google Scholar
• Park, K. K., Surh, Y. J., Steward, B. C., Miller, J. A. (1990). Synthesis and properties of vinyl carbamate epoxide, a possible ultimate electrophilic and carcinogenic metabolite of vinyl carbamate and ethyl carbamate. Biochem Biophys Res Commun 169:1094–1098.
   PubMed Web of Science ®Google Scholar
• Park, K. K, Liem, A., Stewart, B. C., Miller, J. A. (1993). Vinyl carbamate epoxide, a major strong electrophilic, mutagenic, and carcinogenic metabolite of vinyl carbamate and ethyl carbamate (urethane). Carcinogenesis 14:441–450.
   PubMed Web of Science ®Google Scholar
• Ribovich, M. L, Miller, J. A., Miller, E. C., Timmins, L. G. (1982). Labeled 1,N6-ethenoadenosine and 3,N4-ethenocytidine in hepatic RNA of mice given [ethyl-1,2-3H] or [ethyl-1-14C]ethyl carbamate (urethan). Carcinogenesis 3:539–546.
   PubMed Web of Science ®Google Scholar
• Rideout, W. M., 3rd, Coetzee, G. A., Olumi, A. F., Jones, P. A. (1999). 5-methylcytosine as an endogenous mutagen in the human LDL receptor and p53 genes. Science 249:1288–1290.
   Google Scholar
• Salaman, M. H., Roe, F. J. C (1953). Incomplete carcinogens: ethyl carbamate (urethane) as an initiator of skin tumour formation in the mouse. Br J Cancer 7:472–481.
   PubMed Web of Science ®Google Scholar
• Salmon, A. G., Zeise, L. (1991). Carcinogenic effects. In: Salmon, A. G., Zeise, L. ( Eds.), Risks of carcinogenesis from urethane exposure (pp 48–77). Boca Raton, Florida, USA: CRC Press.
   Google Scholar
• Scherer, E., Winterwerp, H., Emmelot, P. (1986). Modification of DNA and metabolism of ethyl carbamate in vivo: formation of 7-(2-oxoethyl)-guanine and its sensitive determination by reductive tritiation using 3H sodium borohydride. In: Singer, B., Bartsch, H. ( Eds.), The role of cyclic nucleic acid adducts in carcinogenesis and mutagenesis (pp 109–125). Lyon, France: IARC Scientific Publications No. 70, International Agency for Research on Cancer.
   Google Scholar
• Schmeltz, I., Chiong, K. G., Hoffman, D. (1978). Formation and determination of ethyl carbamate in tobacco and tobacco smoke. J Anal Toxicol 2:265–268.
   Web of Science ®Google Scholar
• Shimkin, M. B. (1955). Pulmonary tumors in experimental animals. Adv Cancer Res 3:223–267.
   PubMed Web of Science ®Google Scholar
• Shimkin, M. B., Stoner, G. D. (1975). Lung tumors in mice: application to carcinogenesis bioassay. Adv Cancer Res 21:1–58.
   PubMedGoogle Scholar
• Shultz, M. A., Choudar, P. V., Buckpitt, A. R. (1999). Role of murine cytochrome P-450 2F2 in metabolic activation of naphthalene and metabolism of other xenobiotics. J Pharmacol Exp Ther 290:281–288.
   PubMed Web of Science ®Google Scholar
• Sills, R. C., Boorman, J. E., Neal, H. L., Hong, T. R. (1999). Mutations in ras genes in experimental tumours of rodents. IARC Sci Publ 55–86.
   PubMedGoogle Scholar
• Simmonds, A. C., Ghanayem, B. I., Sharma, A., Reilly, C. A., Millen, B., Yost, G., et al. (2004a). Bioactivation of 1,1-dichloroethylene by CYP2E1 and CYP2F2 in murine lung. J Pharmacol Exp Ther 310:855–864.
   PubMed Web of Science ®Google Scholar
• Simmonds, A. C., Reilly, C. A., Baldwin, R. M., Ghanayem, B. I., Lanza, D. L., Yost, G. S., et al. (2004b). Bioactivation of 1,1-dichloroethylene to its epoxide by CYP2E1 and CYP2F enzymes. Drug Metab Dispos 32:1032–1039.
   PubMed Web of Science ®Google Scholar
• Skipper, H. E., Bennett, L. L., Jr., Bryan, C. E., White, L., Jr., Newton, M. A., Simpson, L. (1951). Carbamates in the chemotherapy of leukemia: overall tracer studies on carbonyl-labeled urethan, methylene-labeled urethane, and methylene-labeled ethyl alcohol. Cancer Res 11:46–51.
   PubMed Web of Science ®Google Scholar
• Sun, B., Heddle, J. A. (1999). The relationship between mutant frequency and time in vivo: simple predictions for any tissue, cell type, mutagen. Mutat Res 425:179–183.
   PubMed Web of Science ®Google Scholar
• Swiger, R. R., Cosentino, L., Shima, N., Bielas, J. H., Cruz-Munoz, W., Heddle, J. A. (1999). The cII locus in MutaMouse. Environ Mol Mutagen 34:201–207.
   PubMed Web of Science ®Google Scholar
• Tannenbaum, A. (1964). Contribution of urethane studies to the understanding of carcinogenesis. Natl Cancer Inst Monogr 14:341–356.
   PubMedGoogle Scholar
• Tao, K. S., Urlando, C., Heddle, J. A. (1993). Comparison of somatic mutations in transgenic versus host locus. Proc Natl Acad Sci U S A 90:10681–10685.
   PubMed Web of Science ®Google Scholar
• Thaete, L. G., Gunning, W. T., Stoner, G. D., Malkinson, A. M. (1987). Cellular derivation of lung tumors in sensitive and resistant strains of mice: results at 28 and 56 weeks after urethan treatment. J Natl Cancer Inst 78:743–749.
   PubMed Web of Science ®Google Scholar
• Thorgeirsson, U. P., Dalgard, D. W., Reeves, J., Adamson, R. H. (1994). Tumor incidence in a chemical carcinogenesis study of nonhuman primates. Regul Toxicol Pharmacol 19:130–151.
   PubMed Web of Science ®Google Scholar
• Titis, A. P., Forkert, P. G. (2001). Strain-related differences in bioactivation of vinyl carbamate and formation of DNA adducts in lungs of A/J, CD-1, and C57BL/6 mice. Toxicol Sci 59:82–91.
   PubMed Web of Science ®Google Scholar
• Tomisawa, M., Suemizu, H., Ohnishi, Y., Maruyama, C., Urano, K., Usui, T. K., et al. (2003). Mutation analysis of vinyl carbamate or urethane induced lung tumors in rasH2 transgenic mice. Toxicol. Lett 142:111–117.
   Google Scholar
• Williams, C. V., Fletcher, K., Ashby, J. (1998). Mutagenicity of ethyl carbamate to lazZ− transgenic mice. Mutagenesis 13:133–137.
   PubMed Web of Science ®Google Scholar
• Yamamoto, T., Pierce, W. M., Jr., Hurst, H. E., Chen, D., Waddell, W. J. (1990). Ethyl carbamate metabolism: in vivo inhibitors and in vitro enzymatic systems. Drug Metab. Dispos. 18:276–280.
   PubMed Web of Science ®Google Scholar
• Yan, B., Yan, D., Brady, M., Parkinson, A. (1995). Rat testicular carboxylesterases: cloning, cellular localization, and relationship to liver hydrolase A. Arch Biochem Biophys 316:899–908.
   PubMed Web of Science ®Google Scholar
• Zimmerli, B., Schlatter, J. (1991). Ethyl carbamate: analytical methodology, occurrence, formation, biological activity, and risk assessment. Mutat Res 259:325–350.
   PubMed Web of Science ®Google Scholar