Mutagenicity of cytochrome P450 2E1 substrates in the Ames test with the metabolic competent S. typhimurium strain YG7108pin3ERb5

Toxicology

Volumn 228, Issue 1, 2006, Pages 66-76

  Emmert, Birgit ^a   Bünger, Jürgen ^b   Keuch, Kristian ^a   Müller, Michael ^a   Emmert, Steffen ^a   Hallier, Ernst ^a   Westphal, Götz A ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

^b INSTITUT DER RUHR UNIVERSITÄT BOCHUM IPA   (Germany)

Author keywords

Allyl chloride; Cytochrome P450 2E1; Salmonella microsome assay

Indexed keywords

2 AMINOANTHRACENE; 2 FLUORENYLAMINE; ACETAMIDE; ACRYLAMIDE; ACRYLIC ACID ETHYL ESTER; ACRYLONITRILE; ALLYL CHLORIDE; AROMATIC AMINE; BENZO[A]PYRENE; CYTOCHROME B5; CYTOCHROME P450 2E1; CYTOCHROME P450 REDUCTASE; DIETHYLNITROSAMINE; HETEROCYCLIC AMINE; METHACRYLIC ACID METHYL ESTER; METHYLTRANSFERASE; N NITROSOPYRROLIDINE; PLASMID DNA; POLYCYCLIC AROMATIC HYDROCARBON; PROPYLENE OXIDE; STABILIZING AGENT; TETRACHLOROETHYLENE; TRICHLOROETHYLENE; URETHAN; VINYL ACETATE; WATER;

ALKYLATION; AMES TEST; ARTICLE; BACTERIAL STRAIN; BACTERIUM TRANSFORMATION; CONCENTRATION RESPONSE; CONTROLLED STUDY; DISSOLUTION; ELECTRON TRANSPORT; ENZYME DEFICIENCY; ENZYME SUBSTRATE; FALSE NEGATIVE RESULT; GENETIC TRANSFECTION; GENOTOXICITY; METABOLIC ACTIVATION; MOLECULAR WEIGHT; MUTAGENICITY; NONHUMAN; PRIORITY JOURNAL; SALMONELLA TYPHIMURIUM; SENSITIVITY ANALYSIS; SOLUBILITY;

CYTOCHROME P-450 CYP2E1; DNA, BACTERIAL; DOSE-RESPONSE RELATIONSHIP, DRUG; MUTAGENICITY TESTS; MUTAGENS; PLASMIDS; SALMONELLA TYPHIMURIUM; SPECIES SPECIFICITY; SUBSTRATE SPECIFICITY; TRANSFECTION; XENOBIOTICS;

BACTERIA (MICROORGANISMS);

EID: 33749589444     PISSN: 0300483X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tox.2006.08.013     Document Type: Article

References (71)

1. Albert R.E. Allergic contact sensitizing chemicals as environmental Carcinogens. Environ. Health. Perspect. 105 (1997) 940-948
2. Baum M., Fauth E., Fritzen S., Herrmann A., Mertes P., Merz K., Rudolphi M., Zankl H., and Eisenbrand G. Acrylamide and glycidamide: genotoxic effects in V79-cells and human blood. Mutat. Res. 580 (2005) 61-69
3. Benson R.W., and Beland F.A. Modulation of urethane (ethyl carbamate) carcinogenicity by ethyl alcohol: a review. Int. J. Toxicol. 16 (1997) 521-544
4. Bignami M., Conti G., Conti L., Crebelli R., Misuraca F., Puglia A.M., Randazzo R., Sciandrello G., and Carere A. Mutagenicity of halogenated aliphatic hydrocarbons in Salmonella typhimurium, Streptomyces coelicolor and Aspergillus nidulans. Chem. Biol. Interact. 30 (1980) 9-23
5. Bootman J., Lodge D.C., and Whally H.E. Mutagenic activity of propylene oxide in bacterial and mammalian systems. Mutat. Res. 67 (1979) 101-112
6. Birnboim H.C., and Doly J. A rapid alkaline extraction procedure for screening recombinant plasmid DNA. Nucl. Acids Res. 7 (1979) 1513-1523
7. Burke D.A., Wedd D.J., Herriott D., Bayliss M.K., Spalding D.J.M., and Wilcox P. Evaluation of pyrazole and ethanol fraction in bacterial mutagenicity testing. Mutat. Res. 9 (1994) 23-29
8. Bull R.J., Robinson M., Laurie R.D., Stoner G.D., Greisiger E., Meier J.R., and Stober J. Carcinogenic effects of acrylamide in sencar and A/J mice. Cancer Res. 44 (1984) 107-111
9. Cooper M.T., and Porter T.D. Mutagenicity of nitrosamines in methyltransferase-deficient strains of Salmonella typhimurium coexpressing human cytochrome P450 2E1 and reductase. Mutat. Res. 454 (2000) 45-52
10. Cooper M.T., and Porter T.D. Cytochrome b(5) coexpression increases the CYP2E1-dependent mutagenicity of dialkylnitrosamines in methyltransferase-deficient strains of Salmonella typhimurium. Mutat. Res. 484 (2001) 61-68
11. Dean B.J., Brooks T.M., Hodson-Walker G., and Hutson D.H. Genetic toxicology testing of 41 industrial chemicals. Mutat. Res. 153 (1985) 57-77
12. DeFlora S., Zanacchi P., Camoirano A., Bennicelli C., and Badolati G.S. Genotoxic activity and potency of 135 compounds in the Ames reversion test and in a bacterial DNA-repair test. Mutat. Res. 133 (1984) 161-198
13. DFG. Allyl chloride. In: Greim H. (Ed). Occupational toxicants. Critical evaluation for the MAK values and classification of carcinogens (2002), Wiley/VCH, Weinheim, Germany 1-18
14. Dreeßen B., Westphal G., Hallier E., and Müller M. Mutagenicity of the glutathione and cysteine S-conjugates of the haloalkenes1,1,2-trichloro-3,3,3-trifluoro-1-propene and trichlorofluoroethene in the Ames test in comparison with the tetrachloroethene-analogues. Mutat. Res. 539 (2003) 157-166
15. Dybing E., Soderlund E.J., Gordon W.P., Holme J.A., Christensen T., Becher G., Rivedal E., and Thorgeirsson S.S. Studies on the mechanism of acetamide hepatocarcinogenicity. Pharmacol. Toxicol. 60 (1987) 9-16
16. Eder E., Neudecker T., Lutz D., and Henschler D. Mutagenic potential of allyl and allylic compounds. Structure-activity relationship as determined by alkylating and direct in vitro mutagenic properties. Biochem. Pharmacol. 29 (1980) 993-998
17. Eder E., Neudecker T., Lutz D., and Henschler D. Correlation of alkylating and mutagenic activities of allyl and allylic compounds: standard alkylation test vs. kinetic investigation. Chem. Biol. Interact. 38 (1982) 303-315
18. Eder E., Lutz D., and Jorns M. Allylic compounds bind directly to DNA: investigations of the binding mechanisms in vitro. Chem. Biol. Interact. 61 (1987) 97-108
19. Eder E., and Zugelder J.P. DNA-binding studies with allyl chloride and allyl bromide using the isolated rat liver technique. Toxicol. in Vitro 4 (1990) 661-665
20. El Hadri L., Chanas B., and Ghanayem B.I. Comparative metabolism of methacrylonitrile and acrylonitrile to cyanide using cytochrome P4502E1 and microsomal epoxide hydrolase-null mice. Toxicol. Appl. Pharmacol. 205 (2005) 116-125
21. Friedman M.A., Dulak L.H., and Stedham M.A. A lifetime oncogenicity study in rats with acrylamide. Fundam. Appl. Toxicol. 27 (1995) 95-105
22. Fujita K., and Kamataki T. Predicting the mutagenicity of tobacco-related N-nitrosamines in humans using 11 strains of Salmonella typhimurium YG7108, each coexpressing a form of human cytochrome P450 along with NADPH-cytochrome P450 reductase. Environ. Mol. Mutagen. 38 (2001) 339-346
23. Gatehouse D., Haworth S., Cebula T., Gocke E., Kier L., Matsushima T., Melcion C., Nohmi T., Ohta T., Venitt S., et al. Recommendations for the performance of bacterial mutation assays. Mutat. Res. 312 (1994) 217-233
24. 6-alkylguanine-DNA alkyltransferases. J. Biol. Chem. 272 (1997) 8332-8339
25. Guengerich F.P., Kim D.H., and Iwasaki M. Role of human cytochrome P-450 2E1 in the oxidation of many low molecular weight cancer suspects. Chem. Res. Toxicol. 4 (1991) 168-179
26. Gupta R., and Dani H.M. In vitro formation of organ-specific ultimate carcinogens of 4-dimethylaminoazobenzene and urethan by microsomes. Toxicol. Lett. 45 (1989) 49-54
27. Hanahan D. Studies on the transformation of Escherichia coli with plasmids. J. Mol. Biol. 166 (1983) 557-580
28. Hashimoto K., and Tanii H. Mutagenicity of acrylamide and its analogues in Salmonella typhimurium. Mutat. Res. 158 (1985) 129-133
29. Hengstler J.G., Bogdanffy M.S., Bolt H.M., and Oesch F. Challenging dogma: thresholds for genotoxic carcinogens? The case of vinyl acetate. Annu. Rev. Pharmacol. Toxicol. 43 (2003) 485-520
30. Henschler D. Metabolism of chlorinated alkenes and alkanes as related to toxicity. J. Environ. Pathol. Toxicol. 1 (1977) 125-133
31. Hübner P., Groux P.M., Weibel B., Sengstag C., Horlbeck J., Leong-Morgenthaler P.M., and Luthy J. Genotoxicity of ethyl carbamate (urethane) in Salmonella, yeast and human lymphoblastoid cells. Mutat. Res. 390 (1997) 11-19
32. IARC. Monogr. Eval. Carcinog. Risks Hum.: Acetamide 71 (1999) 1211-1221
33. IARC. Monogr. Eval. Carcinog. Risks Hum.: Acrylonitrile 71 (1999) 43-108
34. Johnson K.A., Gorzinski S.J., Bodner K.M., Campbell R.A., Wolf C.H., Friedman M.A., and Mast R.W. Chronic toxicity and oncogenicity study on acrylamide incorporated in the drinking water of Fischer 344 rats. Toxicol. Appl. Pharmacol. 85 (1986) 154-168
35. Josephy P.D., DeBruin L.S., Lord H.L., Oak J.N., Evans D.H., Guo Z., Dong M.S., and Guengerich F.P. Bioactivation of aromatic amines by recombinant human cytochrome P4501A2 expressed in Ames tester strain bacteria: a substitute for activation by mammalian tissue preparations. Cancer Res. 55 (1995) 799-802
36. Josephy P.D., Evans D.H., Parikh A., and Guengerich F.P. Metabolic activation of aromatic amine mutagens by simultaneous expression of human cytochrome P450 1A2, NADPH-cytochrome P450 reductase, and N-acetyltransferase in Escherichia coli. Chem. Res. Toxicol. 11 (1998) 70-74
37. Josephy P.D. Genetically-engineered bacteria expressing human enzymes and their use in the study of mutagens and mutagenesis. Toxicology 181/182 (2002) 255-260
38. Kranendonk M., Laires A., Rueff J., Estabrook W.R., and Vermeulen N.P. Heterologous expression of xenobiotic mammalian-metabolizing enzymes in mutagenicity tester bacteria: an update and practical considerations. Crit. Rev. Toxicol. 30 (2000) 287-306
39. Kushida H., Fujita K., Suzuki A., Yamada M., Endo T., Nohmi T., and Kamataki T. Metabolic activation of N-alkylnitrosamines in genetically engineered Salmonella typhimurium expressing CYP2E1 or CYP2A6 together with human NADPH-cytochrome P450 reductase. Carcinogenesis 21 (2000) 1227-1232
40. Lee R.P., and Forkert P.G. Inactivation of cytochrome P-450 (CYP2E1) and carboxylesterase (hydrolase A) enzymes by vinyl carbamate in murine pulmonary microsomes. Drug Metab. Dispos. 27 (1999) 233-239
41. 6-ethenoadenosine formation, mutagenicity and murine tumor induction as indicators of the generation of an electrophilic epoxide metabolite of the closely related carcinogens ethyl carbamate (urethane) and vinyl carbamate. Carcinogenesis 11 (1990) 463-473
42. Maron D.M., and Ames B.N. Revised methods for the Salmonella mutagenicity test. Mutat. Res. 113 (1983) 173-215
43. McCann J., Choi E., Yamasaky E., and Ames B. Detection of carcinogens as mutagens in the Salmonella/microsome test: assay of 300 chemicals. Proc. Natl. Acad. Sci. U.S.A. 72 (1975) 5135-5139
44. McCoy E.C., Burrows L., and Rosenkranz H.S. Genetic activity of allyl chloride. Mutat. Res. 57 (1978) 11-15
45. McGregor, D.B., 1981. Tier II mutagenic screening of 13 NIOSH priority compounds. Individual compound report: 3-Chloroprene. Juli 1981, NTIS PB 86-239845. Inveresk Research International Ltd., Musselburgh, Scotland; NIOSH, Cincinnati, OH.
46. Moore M.M., Amtower A., Doerr C.L., Brock K.H., and Dearfield K.L. Genotoxicity of acrylic acid, methyl acrylate, ethyl acrylate, methyl methacrylate, and ethyl methacrylate in L5178Y mouse lymphoma cells. Environ. Mol. Mutagen. 11 (1988) 49-63
47. Moore M.M., and Harrington-Brock K.H. Mutagenicity of trichloroethylene and its metabolites: implications for the risk assessment of trichloroethylene. Envrion. Health. Persp. 108 Suppl. (2000)
48. 6-alkylguanine-DNA alkyltransferases from rat liver and E. coli. Carcinogenesis 6 (1985) 1027-1031
49. NCI, 1978. Bioassay of allyl chloride for possible carcinogenicity. NCI-CG-Tr-73. National Cancer Institute Technical Report Series No. 73, DHEW Publication No. (NIH) 78-1323. US Department of Health Service, NIH.
50. Neudecker T., and Henschler D. Mutagenicity of chloro-olefines in the Salmonella/mammalian microsome test. Mutat. Res. 157 (1985) 145-148
51. Neudecker T., Lutz D., Eder E., and Henschler D. Structure-activity relationship in halogen and alkyl substituted allyl and allylic compounds: correlation of alkylating and mutagenic properties. Biochem. Pharmacol. 29 (1980) 2611-2617
52. NTP. Toxicology and carcinogenesis studies of acrylonitrile (CAS No. 107-13-1) in B6C3F1 mice (gavage studies). Natl. Toxicol. Program. Tech. Rep. Ser. 506 (2001) 1-201
53. Okochi E., Namai E., Ito K., and Mochizuki M. Activation of N-nitrosodialkylamines to mutagens by a metalloporphyrin/oxidant model system for cytochrome P450. Biol. Pharm. Bull. 18 (1995) 49-52
54. Ong T., Mukhtar M., Wolf C.R., and Zeiger E. Differential effects of cytochrome P450-inducers on promutagenactivation capabilities and enzymatic activities of S-9 from ratliver. J. Environ. Pathol. Toxicol. 4 (1980) 55-65
55. Peiler D., Rustemeyer T., Pflug B., and Frosch P. Allergic contact dermatitis in dental laboratory technicians. Part II: Major allergens and their clinical relevance. Dermatosen Beruf Umwelt 48 (2000) 48-54
56. Schiffmann D., Eder E., Neudecker T., and Henschler D. Induction of unscheduled DNA synthesis in HeLa cells by allylic compounds. Cancer Lett. 20 (1983) 263-269
57. Schweikl H., Schmalz G., and Rackebrandt K. The mutagenic activity of unpolymerized resin monomers in Salmonella typhimurium and V79 cells. Mutat. Res. 415 (1998) 119-130
58. 14C]acrylamide. Carcinogenesis 16 (1995) 1161-1165
59. (5) enzymes. Arch. Biochem. Biophys. 435 (2005) 207-216
60. Sumner S.C., Fennell T.R., Moore T.A., Chanas B., Gonzalez F., and Ghanayem B.I. Role of cytochrome P450 2E1 in the metabolism of acrylamide and acrylonitrile in mice. Chem. Res. Toxicol. 12 (1999) 1110-1116
61. Tareke E., Rydberg P., Karlsson P., Eriksson S., and Törnqvist M. Acrylamide: a cooking carcinogen?. Chem. Res. Toxicol. 13 (2000) 517-522
62. Thilly W.G. Dead cells don't form mutant colonies: a serious source of bias in mutation assays. Environ. Mutagen. 7 (1985) 255-258
63. Tomenson J.A., Carpenter A.V., and Pemberton M.A. Critical review of the epidemiology literature on the potential cancer risks of methyl methacrylate. Int. Arch. Occup. Environ. Health. 78 (2005) 603-612
64. Vamvakas S., Herkenhoff M., Dekant W., and Henschler D. Mutagenicity of tetrachloroethene in the Ames test-metabolic activation by conjugation with glutathione. J. Biochem. Toxicol. 4 (1989) 21-27
65. Waegemaekers T.H., and Bensink M.P. Non-mutagenicity of 27 aliphatic acrylate esters in the Salmonella-microsome test. Mutat. Res. 137 (1984) 95-102
66. Wang H., Chanas B., and Ghanayem B.I. Cytochrome P450 2E1 (CYP2E1) is essential for acrylonitrile metabolism to cyanide: comparative studies using CYP2E1-null and wild-type mice. Drug. Metab. Dispos. 30 (2002) 911-917
67. Westphal G.A., Blaszkewicz M., Leutbecher M., Müller A., Hallier E., and Bolt H.M. Bacterial mutagenicity of 2-chloro-1,3-butadiene (chloroprene) caused by decomposition products. Arch. Toxicol. 68 (1994) 79-84
68. Westphal G.A., Bünger J., Schulz T., Müller M., and Hallier E. Mutagenicity of N-nitrosodiethylamine in the Ames test with S. typhimurium TA1535 is due to volatile metabolites and not dependent on cytochrome P450 2E1 induction. Arch. Toxicol. 74 (2000) 638-641
69. 6-methylguanidine. J. Bacteriol. 177 (1995) 1511-1519
70. Zeiger E., Anderson B., Haworth S., Lawlor T., and Mortelmans K. Salmonella mutagenicity tests. IV. Results from the testing of 300 chemicals. Environ. Mol. Mutagen. 11 Suppl. 12 (1988) 1-158
71. Zeiger E., Haseman J.K., Shelby M.D., Margolin B.H., and Tennant R.W. Evaluation of four in vitro genetic toxicity tests for predicting rodent carcinogenicity: confirmation of earlier results with 41 additional chemicals. Environ. Mol. Mutagen. 16 Suppl. 18 (1990) 1-14