In vitro metabolism and covalent binding of ethylbenzene to microsomal protein as a possible mechanism of ethylbenzene-induced mouse lung tumorigenesis

Regulatory Toxicology and Pharmacology

Volumn 57, Issue 2-3, 2010, Pages 129-135

  Saghir, Shakil A ^a   Zhang, Fagen ^a   Rick, David L ^a   Kan, Lynn ^a   Bus, James S ^a   Bartels, Michael J ^a  

^a DOW CHEMICAL COMPANY   (United States)

Author keywords

Ethylbenzene; Liver and lung microsomes; Protein binding; Rat, mouse and human microsomal metabolism; Reactive metabolites of EB

Indexed keywords

5 PHENYL 1 PENTYNE; CELL PROTEIN; CYTOCHROME P450; CYTOCHROME P450 2E1; CYTOCHROME P450 2F2; CYTOCHROME P450 INHIBITOR; DIETHYLDITHIOCARBAMIC ACID; ETHYLBENZENE; ISOENZYME; MICROSOME PROTEIN; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; UNCLASSIFIED DRUG;

ADOLESCENT; ADULT; AGED; ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; BINDING ASSAY; CHILD; CONTROLLED STUDY; COVALENT BOND; ENZYME ACTIVITY; FEMALE; HUMAN; HUMAN CELL; HUMAN TISSUE; IN VITRO STUDY; LIVER MICROSOME; LUNG CANCER; LUNG CARCINOGENESIS; LUNG MICROSOME; MALE; METABOLITE; MICROSOME; MOUSE; NONHUMAN; PRIORITY JOURNAL; PROTEIN BINDING; RAT; TOXICOKINETICS;

ANIMALS; BENZENE DERIVATIVES; CYTOCHROME P-450 CYP1A1; CYTOCHROME P-450 CYP2B1; CYTOCHROME P-450 CYP2E1; CYTOCHROME P-450 ENZYME SYSTEM; ENVIRONMENTAL POLLUTANTS; ENZYME INHIBITORS; FEMALE; HUMANS; LUNG; LUNG NEOPLASMS; MALE; MICE; MICE, INBRED STRAINS; MICROSOMES; MICROSOMES, LIVER; PROTEIN BINDING; RATS; RATS, INBRED F344; SPECIES SPECIFICITY;

RATTUS;

EID: 77953360710     PISSN: 02732300     EISSN: 10960295     Source Type: Journal    
DOI: 10.1016/j.yrtph.2010.01.003     Document Type: Article

References (40)

1. Baillie T.A. Future of toxicology-metabolic activation and drug design: challenges and opportunities in chemical toxicology. Chem. Res. Toxicol. 2006, 19:889-893.
2. Cappaert N.L., Klis S.F., Muijser H., Kulig B.M., Ravensberg L.C., Smoorenburg G.F. Differential susceptibility of rats and guinea pigs to the ototoxic effects of ethyl benzene. Neurotoxicol. Teratol. 2002, 24:503-510.
3. Carlson G.P., Perez Rivera A.A., Mantick N.A. Metabolism of the styrene metabolite 4-vinylphenol by rat and mouse liver and lung. J. Toxicol. Environ. Health 2001, 63:541-551.
4. Charest-Tardif G., Tardif R., Krishnan K. Inhalation pharmacokinetics of ethylbenzene in B6C3F1 mice. Toxicol. Appl. Pharmacol. 2006, 210:63-69.
5. Cavalieri E.L., Li K.M., Balu N., Saeed M., Devanesan P., Higginbotham S., Zhao J., Gross M.L., Rogan E.G. Catechol ortho-quinones: the electrophilic compounds that form depurinating DNA adducts and could initiate cancer and other diseases. Carcinogenesis 2002, 23:1071-1077.
6. Dean B.J., Brooks T.M., Walker G.H., Hutson D.H. Genetic toxicity testing of 41 industrial chemicals. Mutat. Res. 1985, 153:57-77.
7. DeCaprio A.P. The toxicology of hydroquinone - relevance to occupational and environmental exposure. Crit. Rev. Toxicol. 1999, 29:283-330.
8. Devereux T.R., Domin B.A., Philpot R.M. Xenobiotic metabolism by isolated pulmonary cells. Pharmacol. Ther. 1989, 41:243-256.
9. Engstrom K.M. Metabolism of inhaled ethylbenzene in rats. Scand. J. Work Environ. Health 1984, 10:83-87.
10. Evans D.C., Watt A.P., Nicoll-Griffith D.A., Baillie T.A. Drug-protein adducts: an industry perspective on minimizing the potential for drug bioactivation in drug discovery and development. Chem. Res. Toxicol. 2004, 17:3-16.
11. Faber W.D., Roberts L.S., Stump D.G., Tardif R., Krishnan K., Tort M., Dimond S., Dutton D., Moran E., Lawrence W. Two generation reproduction study of ethylbenzene by inhalation in Crl-CD rats. Birth Defects Res. B Dev. Reprod. Toxicol. 2006, 77:10-21.
12. Fishbein L. An overview of environmental and toxicological aspects of aromatic hydrocarbons. IV. Ethylbenzene. Sci. Total Environ. 1985, 44:269-287.
13. Fuciarelli, A.F., 2000. Ethylbenzene: Two Week Repeated Dose Inhalation Study Report. NTP Task Number CHEMO2477, Battelle, Richland, WA.
14. Fustinoni S., Buratti M., Giampiccolo R., Colombi A. Biological and environmental monitoring of exposure to airborne benzene and other aromatic hydrocarbons in Milan traffic wardens. Toxicol. Lett. 1995, 77:387-392.
15. Green T., Toghill A., Foster J.R. The role of cytochromes P-450 in styrene induced pulmonary toxicity and carcinogenicity. SIRC Rev. 2003, 9:62-72.
16. Hellmold H., Overvik E., Stromstedt M., Gustafsson J.-A. Cytochrome P450 forms in the rodent lung involved in the metabolic activation of food-derived heterocyclic amines. Carcinogenesis 1993, 14:1751-1757.
17. Holz O., Scherer G., Brodtmeier S. Determination of low level exposure to volatile aromatic hydrocarbons and genotoxic effects in workers to styrene at a styrene plant. Environ. Med. 1995, 52:420-428.
18. IARC (International Agency of Research in Cancer) 2000. Working Group, Ethylbenzene. In: IARC Monographs on the Evaluation of Carcinogenic Risks to Humans, vol. 77. IARC Press, Lyon, pp. 227-266.
19. Kawai T., Yasugi T., Mizunuma K., Horiguchi S., Iguchi H., Uchida Y., Iwami O., Ikeda M. Comparative evaluation of urinalysis and blood analysis as means of detecting exposure to organic solvents at low concentrations. Int. Arch. Occup. Environ. Health 1992, 64:223-234.
20. Keith I.M., Olson E.B., Wilson N.M., Jefcoate C.R. Immunological identification and effects of 3-methylcholanthrene and phenobarbital on rat pulmonary cytochrome P-450. Cancer Res. 1987, 47:1878-1882.
21. Kennedy S.W., Jones S.P. Simultaneous measurement of cytochrome P4501A catalytic activity and total protein concentration with a fluorescence plate reader. Anal. Biochem. 1994, 222:217-223.
22. MacGregor D.B., Brown A., Cattanach P., Edwards I., McBride D., Riach C., Caspary W.J. Responses of the L5178Y/tk+/tk- mouse lymphoma cell forward mutation assay: III. 72 coded chemicals. Environ. Mol. Mutagen. 1988, 12:85-154.
23. Maltoni C., Conti B., Cotti G., Belpoggi F. Experimental studies on benzene carcinogenicity at the Bologna Institute of Oncology: current results and ongoing research. Am. J. Ind. Med. 1985, 7:415-446.
24. Midorikawa K., Uchidab T., Okamotob Y., Todab C., Sakaib Y., Uedab K., Hirakua Y., Murataa M., Kawanishia S., Kojimab N. Metabolic activation of carcinogenic ethylbenzene leads to oxidative DNA damage. Chem. Biol. Interact. 2004, 150:271-281.
25. National Toxicology Program (NTP) 1992. Toxicity Studies of Ethylbenzene in F344/N Rats and B6C3F1 Mice (Inhalation Studies). Toxicity Study Report Series No. 10. NIH Publications No. 92-3129. U.S. DHHS, PHS, NIH, Research Triangle Park, North Carolina.
26. National Toxicology Program (NTP) 1999. Toxicology and Carcinogenesis Studies of Ethylbenzene (CAS No. 100-41-4) in F344/N Rats and B6C3F1 Mice (Inhalation Studies). NTP TR 466, NIH Publications No. 96-3956.
27. Nestmann E.R., Lee E.G.-H., Matula T.I., Douglas G.R., Mueller J.C. Mutagenicity of constituents identified in pulp and paper mill effluents using the Salmonella/mammalian-microsome assay. Mutat. Res. 1980, 79:203-212.
28. Norppa H., Vainio H. Induction of sister-chromatid exchanges by styrene analogues in cultured human lymphocytes. Mutat. Res. 1983, 116:379-387.
29. Pohl L.R., Branchflower R.V. Covalent binding of electrophilic metabolites to macromolecules. Methods Enzymol. 1981, 77:43-50.
30. Reinke L.A., Moyer M.J. A microsomal oxidation which is highly inducible by ethanol. Drug Metab. 1985, 13:548-552.
31. Saghir S.A., Rick D.L., McClymont E.L., Zhang F., Bartels M.J., Bus J.S. Mechanism of ethylbenzene-induced mouse-specific lung tumor: metabolism of ethylbenzene by rat, mouse and human liver and lung microsomes. Toxicol. Sci. 2009, 107:352-366.
32. Smith G.B.J., Harper P.A., Wong J.M.Y., Lam M.S.M., Reid K.R., Petsikas D., Massey T.E. Human lung microsomal cytochrome P4501A1 (CYP1A1) activities: impact of smoking status and CYP1A1, aryl hydrocarbon receptor, and glutathione S-transferase M1 genetic polymorphisms. Cancer Epidemiol. Biomarkers Prev. 2001, 10:839-853.
33. Stott W.T., Johnson K.A., Day S.J., McGuirk R.J. Ethylbenzene: Mechanism of Tumorigenicity in Fischer 344 Rats and B6C3F1 Mice. Report of Toxicology & Environmental Research and Consulting 1999, The Dow Chemical Company, Midland, Michigan.
34. Stott W.T., Johnson K.A., Day S.J., McGuirk R.J. Ethylbenzene: Four-Week Mechanism of Tumorigenicity Study in Fischer 344 Rats and B6C3F1 Mice. Report of Toxicology & Environmental Research and Consulting 2001, The Dow Chemical Company, Midland, Michigan.
35. Thompson J.A., Bolton J.L., Malkinson A.M. Relationship between the metabolism of butylated hydroxytoluene (BHT) and lung tumor promotion in mice. Exp. Lung Res. 1991, 17:439-453.
36. van Kleef R.G.D.M., Viverberg H.P.M., Westerink R.H.S. Selective inhibition of human heteromeric α9α10 nicotinic acetylcholine receptors at a low agonist concentration by low concentrations of ototoxic organic solvents. Toxicol. In Vitro 2008, 22:1568-1572.
37. Wheeler C.W., Guenthner T.M. Cytochrome P-450-dependent metabolism of xenobiotics in human lung. J. Biochem. Toxicol. 1991, 6:163-169.
38. Zahid M., Saeed M., Rogan E.G., Cavalieri E.L. Benzene and dopamine catechol quinones could initiate cancer or neurogenic disease. Free Radic. Biol. Med. 2010, 48:318-324.
39. Zeiger E., Anderson B., Haworth S., Lawlor T., Mortelmans K. Salmonella mutagenicity tests: V. Results from the testing of 311 chemicals. Environ. Mol. Mutagen. 1992, 19(Suppl. 21):2-141.
40. Zhang F., Yao D., Hua Y., van Breemen R.B., Bolton J.L. Synthesis and reactivity of the catechol metabolites from the equine estrogen, 8,9-dehydroestrone. Chem. Res. Toxicol. 2001, 14:754-763.