Evidence for cellular protein covalent binding derived from styrene metabolite

Chemico-Biological Interactions

Volumn 186, Issue 3, 2010, Pages 323-330

  Yuan, Wei ^a   Jin, Hua ^b   Chung, Jou Ku ^c   Zheng, Jiang ^b  

^a UNIVERSITY OF WASHINGTON   (United States)

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

^c Archemix Corporation   (United States)

Author keywords

Bioactivation; Protein adduction; Styrene; Styrene oxide

Indexed keywords

CELL PROTEIN; CYSTEINE; CYTOCHROME P450 2E1; DISULFIRAM; LACTATE DEHYDROGENASE; POLYCLONAL ANTIBODY; STYRENE; STYRENE OXIDE;

AIRWAY; ANIMAL CELL; ANIMAL CELL CULTURE; ANIMAL TISSUE; ARTICLE; CELL DEATH; CELL LINE; CHEMICAL STRUCTURE; CONTROLLED STUDY; CYTOTOXICITY; EXPOSURE; GENETIC TRANSFECTION; IMMUNOBLOTTING; LUNG PARENCHYMA; MALE; METABOLITE; MOUSE; NONHUMAN; PROTEIN BINDING; PROTEIN DETERMINATION; PROTEIN MODIFICATION; RADIOACTIVITY; SUPERNATANT; WESTERN BLOTTING; WILD TYPE;

ANIMALS; CELL LINE; CYTOCHROME P-450 CYP2E1; CYTOTOXINS; EPOXY COMPOUNDS; HUMANS; MALE; MICE; PROTEIN BINDING; PROTEINS; STYRENE;

ANIMALIA;

EID: 77954384175     PISSN: 00092797     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cbi.2010.05.004     Document Type: Article

References (52)

1. Bond J.A. Review of the toxicology of styrene. Crit. Rev. Toxicol. 1989, 19:227-249.
2. Lewis R.J., Tatken R.L. Registry of Toxic Effects of Chemical Substances 1980, vol. 2. U.S. Department of Health and Human Services, Cincinnati, OH.
3. Ohashi Y., Nakai Y., Ikeoka H., Koshimo H., Esaki Y., Horiguchi S., Teramoto K. Electron microscopic study of the respiratory toxicity of styrene. Osaka City Med. J. 1985, 31:11-21.
4. Ohashi Y., Nakai Y., Ikeoka H., Koshimo H., Nakata J., Esaki Y., Horiguchi S., Teramoto K. Degeneration and regeneration of respiratory mucosa of rats after exposure to styrene. J. Appl. Toxicol. 1986, 6:405-412.
5. Cruzan G., Cushman J.R., Andrews L.S., Granville G.C., Miller R.R., Hardy C.J., Coombs D.W., Mullins P.A. Subchronic inhalation studies of styrene in CD rats and CD-1 mice. Fundam. Appl. Toxicol. 1997, 35:152-165.
6. Cruzan G., Cushman J.R., Andrews L.S., Granville G.C., Johnson K.A., Hardy C.J., Coombs D.W., Mullins P.A., Brown W.R. Chronic toxicity/oncogenicity study of styrene in CD rats by inhalation exposure for 104 weeks. Toxicol. Sci. 1998, 46:266-281.
7. Cruzan G., Cushman J.R., Andrews L.S., Granville G.C., Johnson K.A., Bevan C., Hardy C.J., Coombs D.W., Mullins P.A., Brown W.R. Chronic toxicity/oncogenicity study of styrene in CD-1 mice by inhalation exposure for 104 weeks. J. Appl. Toxicol. 2001, 21:185-198.
8. Stewart R.D., Dodd H.C., Baretta E.D., Schaffer A.W. Human exposure to styrene vapor. Arch. Environ. Health 1968, 16:656-662.
9. Chmielewski J., Renke W. Clinical and experimental studies on the pathogenesis of toxic effects of styrene. II. The effect of styrene on the respiratory system. Bull. Inst. Marit. Trop. Med. Gdynia. 1975, 26:299-302.
10. Carlson G.P. Critical appraisal of the expression of cytochrome P450 enzymes in human lung and evaluation of the possibility that such expression provides evidence of potential styrene tumorigenicity in humans. Toxicology 2008, 254:1-10.
11. Phillips D.H., Farmer P.B. Evidence for DNA and protein binding by styrene and styrene oxide. Crit. Rev. Toxicol. 1994, 24(Suppl.):S35-46.
12. Fleig I., Thiess A.M. Mutagenicity study of workers employed in the styrene and polystyrene processing and manufacturing industry. Scand. J. Work Environ. Health 1978, 4(Suppl. 2):254-258.
13. Andersson H.C., Tranberg E.A., Uggla A.H., Zetterberg G. Chromosomal aberrations and sister-chromatid exchanges in lymphocytes of men occupationally exposed to styrene in a plastic-boat factory. Mutat. Res. 1980, 73:387-401.
14. Maki-Paakkanen J., Walles S., Osterman-Golkar S., Norppa H. Single-strand breaks, chromosome aberrations, sister-chromatid exchanges, and micronuclei in blood lymphocytes of workers exposed to styrene during the production of reinforced plastics. Environ. Mol. Mutagen. 1991, 17:27-31.
15. Johanson G., Ernstgard L., Gullstrand E., Lof A., Osterman-Golkar S., Williams C.C., Sumner S.C. Styrene oxide in blood, hemoglobin adducts, and urinary metabolites in human volunteers exposed to (13)C(8)-styrene vapors. Toxicol. Appl. Pharmacol. 2000, 168:36-49.
16. Osterman-Golkar S., Christakopoulos A., Zorcec V., Svensson K. Dosimetry of styrene 7,8-oxide in styrene- and styrene oxide-exposed mice and rats by quantification of haemoglobin adducts. Chem. Biol. Interact. 1995, 95:79-87.
17. Fustinoni S., Colosio C., Colombi A., Lastrucci L., Yeowell-O'Connell K., Rappaport S.M. Albumin and hemoglobin adducts as biomarkers of exposure to styrene in fiberglass-reinforced-plastics workers. Int. Arch. Occup. Environ. Health 1998, 71:35-41.
18. Vodicka P., Tvrdik T., Osterman-Golkar S., Vodickova L., Peterkova K., Soucek P., Sarmanova J., Farmer P.B., Granath F., Lambert B., Hemminki K. An evaluation of styrene genotoxicity using several biomarkers in a 3-year follow-up study of hand-lamination workers. Mutat. Res. 1999, 445:205-224.
19. Vodicka P., Koskinen M., Stetina R., Soucek P., Vodickova L., Matousu Z., Kuricova M., Hemminki K. The role of various biomarkers in the evaluation of styrene genotoxicity. Cancer Detect. Prev. 2003, 27:275-284.
20. Vodicka P., Soucek P., Tates A.D., Dusinska M., Sarmanova J., Zamecnikova M., Vodickova L., Koskinen M., de Zwart F.A., Natarajan A.T., Hemminki K. Association between genetic polymorphisms and biomarkers in styrene-exposed workers. Mutat. Res. 2001, 482:89-103.
21. Christakopoulos A., Bergmark E., Zorcec V., Norppa H., Maki-Paakkanen J., Osterman-Golkar S. Monitoring occupational exposure to styrene from hemoglobin adducts and metabolites in blood. Scand. J. Work Environ. Health 1993, 19:255-263.
22. Beaune P., Pessayre D., Dansette P., Mansuy D., Manns M. Autoantibodies against cytochromes P450: role in human diseases. Adv. Pharmacol. 1994, 30:199-245.
23. Pumford N.R., Halmes N.C. Protein targets of xenobiotic reactive intermediates. Annu. Rev. Pharmacol. Toxicol. 1997, 37:91-117.
24. Boelsterli U.A. Specific targets of covalent drug-protein interactions in hepatocytes and their toxicological significance in drug-induced liver injury. Drug Metab. Rev. 1993, 25:395-451.
25. Brodie B.B., Reid W.D., Cho A.K., Sipes G., Krishna G., Gillette J.R. Possible mechanism of liver necrosis caused by aromatic organic compounds. Proc. Natl. Acad. Sci. U.S.A. 1971, 68:160-164.
26. Yang X.X., Hu Z.P., Chan S.Y., Zhou S.F. Monitoring drug-protein interaction. Clin. Chim. Acta 2006, 365:9-29.
27. Zhou S., Chan E., Duan W., Huang M., Chen Y.Z. Drug bioactivation, covalent binding to target proteins and toxicity relevance. Drug Metab. Rev. 2005, 37:41-213.
28. Hanzlik R.P., Fang J., Koen Y.M. Filling and mining the reactive metabolite target protein database. Chem. Biol. Interact. 2009, 179:38-44.
29. Fang J., Koen Y.M., Hanzlik R.P. Bioinformatic analysis of xenobiotic reactive metabolite target proteins and their interacting partners. BMC Chem. Biol. 2009, 9:5.
30. Pumford N.R., Martin B.M., Hinson J.A. A metabolite of acetaminophen covalently binds to the 56kDa selenium binding protein. Biochem. Biophys. Res. Commun. 1992, 182:1348-1355.
31. Gupta S., Rogers L., Smith C. Inhibition of carbamyl phosphate synthetase I (CPS I) by hepatotoxic doses of acetaminophen (AP) in mice. Fundam. Appl. Toxicol. 1995, 15:153.
32. Landin J.S., Cohen S.D., Khairallah E.A. Identification of a 54-kDa mitochondrial acetaminophen-binding protein as aldehyde dehydrogenase. Toxicol. Appl. Pharmacol. 1996, 141:299-307.
33. Jollow D., Mitchell J., Potter W., Davis D., Gillette J., Brodie B. Acetaminophen-induced hepatic necrosis. II. Role of covalent binding in vivo. J. Pharmacol. Exp. Ther. 1973, 187:195-202.
34. Potter W., Davis D., Mitchell J., Jollow D., Gillette J., Brodie B. Acetaminophen-induced hepatic necrosis: 3. Cytochrome P-450 mediated covalent binding in vitro. J. Pharmacol. Exp. Ther. 1973, 187:203-210.
35. Potter W., Thorgeirsson S., Jollow D., Mitchell J. Acetaminophen-induced hepatic necrosis. V. Correlation of hepatic necrosis, covalent binding and glutathione depletion in hamsters. Pharmacology 1974, 12:129-143.
36. Satoh H., Martin B.M., Schulick A.H., Christ D.D., Kenna J.G., Pohl L.R. Human anti-endoplasmic reticulum antibodies in sera of patients with halothane-induced hepatitis are directed against a trifluoroacetylated carboxylesterase. Proc. Natl. Acad. Sci. U.S.A. 1989, 86:322-326.
37. Butler L.E., Thomassen D., Martin J.L., Martin B.M., Kenna J.G., Pohl L.R. The calcium-binding protein calreticulin is covalently modified in rat liver by a reactive metabolite of the inhalation anesthetic halothane. Chem. Res. Toxicol. 1992, 5:406-410.
38. Bourdi M., Chen W., Peter R.M., Martin J.L., Buters J.T., Nelson S.D., Pohl L.R. Human cytochrome P450 2E1 is a major autoantigen associated with halothane hepatitis. Chem. Res. Toxicol. 1996, 9:1159-1166.
39. Eliasson E., Kenna J.G. Cytochrome P450 2E1 is a cell surface autoantigen in halothane hepatitis. Mol. Pharmacol. 1996, 50:573-582.
40. Guengerich F.P., Kim D.H., Iwasaki M. Role of human cytochrome P-450 IIE1 in the oxidation of many low molecular weight cancer suspects. Chem. Res. Toxicol. 1991, 4:168-179.
41. Halmes N.C., McMillan D.C., Oatis J.E., Pumford N.R. Immunochemical detection of protein adducts in mice treated with trichloroethylene. Chem. Res. Toxicol. 1996, 9:451-456.
42. Halmes N.C., Samokyszyn V.M., Pumford N.R. Covalent binding and inhibition of cytochrome P4502E1 by trichloroethylene. Xenobiotica 1997, 27:101-110.
43. Alarie Y. Sensory irritation of the upper airways by airborne chemicals. Toxicol. Appl. Pharmacol. 1973, 24:279-297.
44. Lanosa M.J., Willis D.N., Jordt S., Morris J.B. Role of metabolic activation and the TRPA1 receptor in the sensory irritation response to styrene and naphthalene. Toxicol. Sci. 2010, (February). (Epub ahead of print).
45. Chung J.K., Yuan W., Liu G., Zheng J. Investigation of bioactivation and toxicity of styrene in CYP2E1 transgenic cells. Toxicology 2006, 226:99-106.
46. Yuan W., Chung J., Gee S., Hammock B.D., Zheng J. Development of polyclonal antibodies for the detection of styrene oxide modified proteins. Chem. Res. Toxicol. 2007, 20:316-321.
47. Van Winkle L.S., Buckpitt A.R., Plopper C.G. Maintenance of differentiated murine Clara cells in microdissected airway cultures. Am. J. Respir. Cell Mol. Biol. 1996, 14:586-598.
48. Jin H., Dai J., Chen X., Liu J., Zhong D., Gu Y., Zheng J. Pulmonary toxicity and metabolic activation of dauricine in CD-1 mice. J. Pharmacol. Exp. Ther. 2009.
49. Watt K.C., Morin D.M., Kurth M.J., Mercer R.S., Plopper C.G., Buckpitt A.R. Glutathione conjugation of electrophilic metabolites of 1-nitronaphthalene in rat tracheobronchial airways and liver: identification by mass spectrometry and proton nuclear magnetic resonance spectroscopy. Chem. Res. Toxicol. 1999, 12:831-839.
50. Hemminki K. Reactions of methylnitrosourea, epichlorohydrin, styrene oxide and acetoxyacetylaminofluorene with polyamino acids. Carcinogenesis 1983, 4:1-3.
51. Hemminki K. Binding of styrene oxide to amino acids, human serum proteins and hemoglobin. Arch. Toxicol. Suppl. 1986, 9:286-290.
52. Linhart I., Mraz J., Scharff J., Krouzelka J., Duskova S., Nohova H., Vodickova L. New urinary metabolites formed from ring-oxidized metabolic intermediates of styrene. Chem. Res. Toxicol. 2010, 23:251-257.