Metabolism of styrene to styrene oxide and vinylphenols in cytochrome P450 2F2- and P450 2E1-knockout mouse liver and lung microsomes

Chemical Research in Toxicology

Volumn 27, Issue 1, 2014, Pages 27-33

  Shen, Shuijie ^a   Li, Lei ^b   Ding, Xinxin ^b   Zheng, Jiang ^a,c,d  

^a SEATTLE CHILDREN S RESEARCH INSTITUTE   (United States)

^b STATE UNIVERSITY OF NEW YORK   (United States)

^c UNIVERSITY OF WASHINGTON SCHOOL OF MEDICINE   (United States)

^d SHENYANG PHARMACEUTICAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

4 VINYLPHENOL; CYTOCHROME P450; CYTOCHROME P450 2E1; CYTOCHROME P450 2F2; LACTATE DEHYDROGENASE; STYRENE DERIVATIVE; STYRENE OXIDE; UNCLASSIFIED DRUG; 4-VINYLPHENOL; EPOXIDE; PHENOL DERIVATIVE; STYRENE;

ANIMAL CELL; ANIMAL EXPERIMENT; ARTICLE; CELL COUNT; CONTROLLED STUDY; CORRELATION ANALYSIS; ENZYME ACTIVITY; EPOXIDATION; HYDROXYLATION; LIVER MICROSOME; LUNG ALVEOLUS CELL; LUNG LAVAGE; LUNG TOXICITY; MALE; METABOLIC ACTIVATION; MOUSE; NONHUMAN; PROTEIN EXPRESSION; ANIMAL; CHEMICAL STRUCTURE; CHEMISTRY; CYTOLOGY; DEFICIENCY; KNOCKOUT MOUSE; LUNG; METABOLISM; MICROSOME;

ANIMALS; CYTOCHROME P-450 ENZYME SYSTEM; EPOXY COMPOUNDS; LUNG; MICE; MICE, KNOCKOUT; MICROSOMES; MICROSOMES, LIVER; MOLECULAR STRUCTURE; PHENOLS; STYRENE;

EID: 84892885364     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx400305w     Document Type: Article

References (35)

1. Miller, R. R., Newhook, R., and Poole, A. (1994) Styrene production, use, and human exposure Crit. Rev. Toxicol. 24 (Suppl) S1-10
2. Hodgson, A. T., Wooley, J. D., and Daisey, J. M. (1993) Emissions of volatile organic compounds from new carpets measured in a large-scale environmental chamber Air Waste 43, 316-324
3. Fleming-Jones, M. E. and Smith, R. E. (2003) Volatile organic compounds in foods: a five year study J. Agric. Food Chem. 51, 8120-8127
4. Tang, W., Hemm, I., and Eisenbrand, G. (2000) Estimation of human exposure to styrene and ethylbenzene Toxicology 144, 39-50
5. Scott, D. and Preston, R. (1994) A critical review of the cytogenetic effects of styrene with an emphasis on human population monitoring: a synopsis Crit. Rev. Toxicol 24 (Suppl) S47-48
6. Leibman, K. C. (1975) Metabolism and toxicity of styrene Environ. Health Perspect. 11, 115-119
7. IARC (1994) IARC monographs on the evaluation of carcinogenic risks to humans: some industrial chemicals: some industrial chemicals IARC Monogr. Eval. Carcinog. Risks Hum. 233-246
8. IARC (2002) Some traditional herbal medicines, some mycotoxins, naphthalene and styrene IARC Monogr. Eval. Carcinog. Risks Hum. 1-556
9. Bond, J. (1989) Review of the toxicology of styrene Crit. Rev. Toxicol. 19, 227-249
10. Brown, N., Lamb, J., Brown, S., and Neal, B. (2000) A review of the developmental and reproductive toxicity of styrene Regul. Toxicol. Pharmacol. 32, 228-247
11. NTP.((2011) Report on Carcinogens, 12 th ed., U.S. Department of Health and Human Services: National Toxicology Program 383, Research Triangle Park, NC.
12. McConnell, E. and Swenberg, J. (1994) Review of styrene and styrene oxide long-term animal studies Crit. Rev. Toxicol. 24 (Suppl) S49-S55
13. Vodicka, P., Koskinen, M., Naccarati, A., Oesch-Bartlomowicz, B., Vodickova, L., Hemminki, K., and Oesch, F. (2006) Styrene metabolism, genotoxicity, and potential carcinogenicity Drug Metab. Rev. 38, 805-853
14. Sumner, S. J. and Fennell, T. R. (1994) Review of the metabolic fate of styrene Crit. Rev. Toxicol. 24 (Suppl) S11-S33
15. NTP. ((2011) Report on Carcinogens, 12 th ed., U.S. Department of Health and Human Services: National Toxicology Program 391, Research Triangle Park, NC.
16. Pantarotto, C., Fanelli, R., Bidoli, F., Morazzoni, P., Salmona, M., and Szczawinska, K. (1978) Arene oxides in styrene metabolism, a new perspective in styrene toxicity? Scand. J. Work Environ. Health 4 (Suppl 2) 67-77
17. Pfaffli, P., Hesso, A., Vainio, H., and Hyvonen, M. (1981) 4-Vinylphenol excretion suggestive of arene oxide formation in workers occupationally exposed to styrene Toxicol. Appl. Pharmacol. 60, 85-90
18. Watabe, T., Hiratsuka, A., Aizawa, T., Sawahata, T., Ozawa, N., Isobe, M., and Takabatake, E. (1982) Studies on metabolism and toxicity of styrene. IV. 1-Vinylbenzene 3,4-oxide, a potent mutagen formed as a possible intermediate in the metabolism in vivo of styrene to 4-vinylphenol Mutat. Res. 93, 45-55
19. Shen, S., Zhang, F., Gao, L., Zeng, S., and Zheng, J. (2010) Detection of phenolic metabolites of styrene in mouse liver and lung microsomal incubations Drug Metab. Dispos. 38, 1934-1943
20. Linhart, I., Mraz, J., Scharff, J., Krouzelka, J., Duskova, S., Nohova, H., and Vodickova, L. (2010) New urinary metabolites formed from ring-oxidized metabolic intermediates of styrene Chem. Res. Toxicol. 23, 251-257
21. Carlson, G. P., Ullman, M., Mantick, N. A., and Snyder, P. W. (2002) 4-Vinylphenol-induced pneumotoxicity and hepatotoxicity in mice Toxicol. Pathol. 30, 565-569
22. Harvilchuck, J. A. and Carlson, G. P. (2006) Comparison of styrene and its metabolites styrene oxide and 4-vinylphenol on cytotoxicity and glutathione depletion in Clara cells of mice and rats Toxicology 227, 165-172
23. Carlson, G. (2003) In vitro metabolism of styrene to styrene oxide in liver and lung of Cyp2E1 knockout mice J. Toxicol. Environ. Health A 66, 861-869
24. Zhang, F., Lowe, E. R., Rick, D. L., Qiu, X., Leibold, E., Cruzan, G., and Bartels, M. J. (2011) In vitro metabolism, glutathione conjugation, and CYP isoform specificity of epoxidation of 4-vinylphenol Xenobiotica 41, 6-23
25. Cruzan, G., Carlson, G., Johnson, K., Andrews, L., Banton, M., Bevan, C., and Cushman, J. (2002) Styrene respiratory tract toxicity and mouse lung tumors are mediated by CYP2F-generated metabolites Regul. Toxicol. Pharmacol. 35, 308-319
26. Choudhary, D., Jansson, I., Schenkman, J. B., Sarfarazi, M., and Stoilov, I. (2003) Comparative expression profiling of 40 mouse cytochrome P450 genes in embryonic and adult tissues Arch. Biochem. Biophys. 414, 91-100
27. Choudhary, D., Jansson, I., Stoilov, I., Sarfarazi, M., and Schenkman, J. B. (2005) Expression patterns of mouse and human CYP orthologs (families 1-4) during development and in different adult tissues Arch. Biochem. Biophys. 436, 50-61
28. Baldwin, R. M., Jewell, W. T., Fanucchi, M. V., Plopper, C. G., and Buckpitt, A. R. (2004) Comparison of pulmonary/nasal CYP2F expression levels in rodents and rhesus macaque J. Pharmacol. Exp. Ther. 309, 127-136
29. Cruzan, G., Bus, J., Banton, M., Gingell, R., and Carlson, G. (2009) Mouse specific lung tumors from CYP2F2-mediated cytotoxic metabolism: an endpoint/toxic response where data from multiple chemicals converge to support a mode of action Regul. Toxicol. Pharmacol. 55, 205-218
30. Carlson, G. (2004) Comparison of the susceptibility of wild-type and CYP2E1 knockout mice to the hepatotoxic and pneumotoxic effects of styrene and styrene oxide Toxicol. Lett. 150, 335-339
31. Simmonds, A. C., Ghanayem, B. I., Sharma, A., Reilly, C. A., Millen, B., Yost, G. S., and Forkert, P. G. (2004) Bioactivation of 1,1-dichloroethylene by CYP2E1 and CYP2F2 in murine lung J. Pharmacol. Exp. Ther. 310, 855-864
32. Forkert, P. G., Baldwin, R. M., Millen, B., Lash, L. H., Putt, D. A., Shultz, M. A., and Collins, K. S. (2005) Pulmonary bioactivation of trichloroethylene to chloral hydrate: relative contributions of CYP2E1, CYP2F, and CYP2B1 Drug Metab. Dispos. 33, 1429-1437
33. Shultz, M. A., Morin, D., Chang, A. M., and Buckpitt, A. (2001) Metabolic capabilities of CYP2F2 with various pulmonary toxicants and its relative abundance in mouse lung subcompartments J. Pharmacol. Exp. Ther. 296, 510-519
34. Cruzan, G., Bus, J., Hotchkiss, J., Harkema, J., Banton, M., and Sarang, S. (2012) CYP2F2-generated metabolites, not styrene oxide, are a key event mediating the mode of action of styrene-induced mouse lung tumors Regul. Toxicol. Pharmacol. 62, 214-220
35. Cruzan, G., Carlson, G. P., Johnson, K. A., Andrews, L. S., Banton, M. I., Bevan, C., and Cushman, J. R. (2002) Styrene respiratory tract toxicity and mouse lung tumors are mediated by CYP2F-generated metabolites Regul. Toxicol. Pharmacol. 35, 308-319