Cytotoxicity of 1,2-epoxynaphthalene is correlated with protein binding and in situ glutathione depletion in cytochrome P4501A1 expressing SF-21 cells

Toxicological Sciences

Volumn 53, Issue 2, 2000, Pages 352-360

  Greene, Jessica F ^a   Zheng, Jiang ^b   Grant, David F ^c   Hammock, Bruce D ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b NORTHEASTERN UNIVERSITY   (United States)

^c UNIVERSITY OF ARKANSAS FOR MEDICAL SCIENCES   (United States)

Author keywords

1,2 epoxynaphthalene; Alkaline permethylation; CYP1A1; Ethyl ester glutathione; Glutathione; Naphthalene; Sf 21

Indexed keywords

CYTOCHROME P450; GLUTATHIONE DERIVATIVE; GLUTATHIONE PEROXIDASE; NAPHTHALENE DERIVATIVE; PROTEIN; THIOL GROUP; UNSPECIFIC MONOOXYGENASE; XENOBIOTIC AGENT;

ANIMAL CELL; ARTICLE; CONTROLLED STUDY; CYTOTOXICITY; DOSE RESPONSE; GAS CHROMATOGRAPHY; IMMUNOBLOTTING; LEPIDOPTERA; MASS SPECTROMETRY; METHYLATION; NONHUMAN; POLYACRYLAMIDE GEL ELECTROPHORESIS; PROTEIN BINDING;

EID: 0033963899     PISSN: 10966080     EISSN: None     Source Type: Journal    
DOI: 10.1093/toxsci/53.2.352     Document Type: Article

References (53)

1. Arey, J., Zielinska, B., Atkinson, T., and Winer, A. (1987). Polycyclic aromatic hydrocarbon and nitroarene concentrations in ambient air during a wintertime high NOx episode in the Los Angeles basin. Atmos. Environ. 21, 1437-1444.
2. Bartolone, J. B., Birge, R. B., Bulera, S. J., Bruno, M. K., Nishanian, E. V., Cohen, S. D., and Khairallah, E. A. (1992). Purification, antibody production, and partial amino acid sequence of the 58-kDa acetaminophen-binding liver proteins. Toxicol. Appl. Pharmacol. 113, 19-29.
3. Bieniek, G. (1994). The presence of 1-naphthol in the urine of industrial workers exposed to naphthalene. Occup. Environ. Med. 51, 357-359.
4. Booth, J., Boyland, E., Sato, T., and Sims, P. (1960). Metabolism of polycyclic compounds: 17. The reaction of 1,2-dihydronaphthalene and 1,2-epoxy-1,2,3,4-tetrahydroxynaphthalene with glutathione catalyzed by tissue preparations. Biochem. J. 77, 182-186.
5. Bourne, M. C., and Young, L. (1934). The metabolism of naphthalene in rabbits. Biochem. J. 28, 803-808.
6. Boyland, E., and Sims, P. (1960). Metabolism of polycyclic compounds: 16. The metabolism of 1,2-dihydronaphthalene and 1,2-epoxy-1,2,3.4-tetrahydroxynaphthalene. Biochem. J. 77, 175-181.
7. Buckpitt, A., Buonarati, M., Avey, L. B., Chang, A. M., Morin, D., and Plopper, C. G. (1992). Relationship of cytochrome P450 activity to Clara cell cytotoxicity: II. Comparison of stereoselectivity of naphthalene epoxidation in lung and nasal mucosa of mouse, hamster, rat, and rhesus monkey. J. Pharmacol Exp. Ther. 261, 364-72.
8. Buckpitt, A., Chang, A. M., Weir, A., Van Winkle, L., Duan, X., Philpot, R., and Plopper, C. (1995). Relationship of cytochrome P450 activity to Clara cell cytotoxicity: IV. Metabolism of naphthalene and naphthalene oxide in microdissected airways from mice, rats, and hamsters. Mol. Pharmacol. 47, 74-81.
9. Buckpitt, A. R., Smart, G., and Baker, B. (1982). Pulmonary bronchiolar damage of naphthalene administered by inhalation. Fed. Proc. 41, 7997-7999.
10. Buckpitt, A. R., and Warren, D. L. (1983). Evidence for hepatic formation, export, and covalent binding of reactive naphthalene metabolites in extrahepatic tissues in vivo. J. Pharmacol. Exp. Ther. 226, 8-16.
11. Bulera, S. J., Birge, R. B., Cohen, S. D., and Khairallah, E. A. (1995). Identification of the mouse liver 44-kDa acetaminophen-binding protein as a subunit of glutamine synthetase. Toxicol. Appl. Pharmacol. 134, 313-320.
12. Burke, M. D., and Mayer, R. T. (1974). Ethoxyresorufin: Direct fluorimetric assay of a microsomal O-dealkylation, which is preferentially inducible by 3-methylcholanthrene. Drug Metab. Disp. 2, 583-588.
13. Charles, J.-P., Wojtasek, H., Lentz, A. J., Thomas, B. A., Bonning, B. C., Palli, S. R., Parker, A. G., Dorman, G., Hammock, B. D., Prestwich, G. D., and Riddiford, L. M. (1996). Purification and reassessment of ligand binding by the recombinant, putative juvenile hormone receptor of the tobacco hornworm, Manduca sexta. Arch. Insect Biochem. Physiol. 31, 371-393.
14. Chichester, C. H., Buckpitt, A. R., Chang, A., and Plopper, C. G. (1994). Metabolism and cytotoxicity of naphthalene and its metabolites in isolated murine Clara cells. Mol Pharmacol. 45, 664-672.
15. Cho, M., Chichester, C., Morin, D., Plopper, C., and Buckpitt, A. (1994a). Covalent interactions of reactive naphthalene metabolites with proteins. J. Pharmacol. Exp. Ther. 269, 881-889.
16. Cho, M., Jedrychowski, R., Hammock, B., and Buckpitt, A. (1994b). Reactive naphthalene metabolite binding to hemoglobin and albumin. Fundam. Appl. Toxicol. 22, 26-33.
17. Cohen, S. D., Pumford, N. R., Khairallah, E. A., Boekelheide, K., Pohl, L. R., Amouzadeh, H. R., and Hinson, J. A. (1997). Selective protein covalent binding and target organ toxicity. Toxicol. Appl. Pharmacol. 143, 1-12.
18. Delescluse, C., Ledirac, N., de Sousa, G., Pralavorio, M., Lesca, P., and Rahmani, R. (1998). Cytotoxic effects and induction of cytochromes P450 1A1/2 by insecticides, in hepatic or epidermal cells: Binding capability to the Ah receptor. Toxicol. Lett. 96, 33-39.
19. Ellman, G. L. (1959). Tissue sulfhydryl groups. Arch. Biochem. Biophys. 82, 70-77.
20. Fahey, R., and Newton, G. (1987). Determination of low-molecular-weight thiols using monobromobimane fluorescent labeling and high performance liquid chromatography. Methods Enzymol. 143, 85-96.
21. Forkert, P.G. (1997). Conjugation of glutathione with the reactive metabolites of 1, 1-dichlorocthylene in murine lung and liver. Microsc. Res. Tech. 36, 234-242.
22. Gonzalez, F. J., Kimura, S., Tamura, S., and Gelboin, H. V. (1991). Expression of mammalian cytochromes P450 using baculovirus. Methods Enzymol. 206, 93-99.
23. Grant, D. F., Bender, D. M. and Hammock, B. D. (1989). Quantitative kinetic assays for glutathione S-transferases and general esterase in individual mosquitoes using an EIA reader. Insect Biochem. 19, 741-751.
24. Grant, D. F., Greene, J. F., Pinot, F., Borhan, B., Moghaddam, M. F., Hammock, B. D., McCutchen, B., Ohkawa, H., Luo, G., and Guenthner, T. M. (1996). Development of an in situ toxicity assay system using recombinant baculoviruses. Biochem. Pharmacol. 51, 503-515.
25. Griffin, K. A., Johnson, C. B., Breger, R. K., and Franklin, R. B. (1983). Toxicity of 2-methylnaphthalene with observations on the hepatic and pulmonary formation of isomeric dihydrodiols inDBA/2J mice. Toxicologist 26, 213-230.
26. Gupta, P., Harger, W. P., and Arey, J. (1996). The contribution of nitro-and methylnitronaphthalenes to the vapor-phase mutagenicity of ambient air samples. Atmos. Environ. 30, 3157-3166.
27. Hill, R. H., Jr., Head, S. L., Baker, S., Gregg, M., Shealy, D. B., Bailey, S. L., Williams, C. C., Sampson, E. J., and Needham, L. L. (1995). Pesticide residues in urine of adults living in the United States: Reference range concentrations. Environ. Res. 71, 99-108.
28. Iverson, S. L., Hu, L. Q., Vukomanovic, V., and Bolton, J. L. (1995). The influence of the p-alkyl substituent on the isomerization of o-quinones to p-quinone methides: Potential bioactivation mechanism for catechols. Chem. Res. Toxicol. 8, 537-544.
29. Juchau, M. R., Boutelet-Bochan, H., and Huang, Y. (1998). Cytochrome-P450-dependent biotransformation of xenobiotics in human and rodent embryonic tissues. Drug Metab. Rev. 30, 541-568.
30. Kirk, R. and Othmer, D. (1981). Naphthalene. In Kirk-Othmer Encyclopedia of Chemical Technology, pp. 698-719. Wiley, New York.
31. Laemmli, U. K. (1970). Cleavage of structural proteins during the assembling of the head of bacteriophage T4. Nature 227, 680-685.
32. Landin, J. S., Cohen, S. D., and Khairallah, E. A. (1996). Identification of a 54-kDa mitochondrial acetaminophen-binding protein as aldehyde dehydrogenase. Toxicol. Appl. Pharmacol. 141, 299-307.
33. Marco, M. P., Nasiri, M., Kurth, M. J., and Hammock, B. D. (1993). Enzyme-linked immunosorbent assay for the specific detection of the mercapturic acid metabolites of naphthalene. Chem. Res. Toxicol. 6, 284-293.
34. McLemore, T. L., Adelberg, S., and Liu, M. C. (1990). Expression of CYP1A1 gene in patients with lung cancer: Evidence for cigarette smoke-induced gene expression in normal lung tissue and for altered gene regulation in primary pulmonary carcinomas. J. Natl. Cancer Inst. 82, 1333-1339.
35. Mumford, J. L., Harris, D. B., Williams, K., Chuang, J. C., and Cooke, M. (1987). Indoor air sampling and mutagenicity studies of emissions from unvented coal combustion. Environ. Sci. Technol. 21, 308-311.
36. Murty, V. S., and Penning, T. M. (1992). Polycyclic aromatic hydrocarbon (PAH) ortho-quinone conjugate chemistry: Kinetics of thiol addition to PAH ortho-quinones and structures of thioether adducts of naphthalene-1,2-dione. Chem. Biol. Interact. 84, 169-188.
37. Nguyen, N., and Tukey, R. (1997). Baculovirus-directed expression of rabbit UDP-glucuronosyltransferases in Spodoptera frugiperda cells. Drug Metab. Disp. 25, 745-749.
38. Nishida, K., Ohta, Y., Ito, M., Nagamura, Y., Kitahara, S., Fujii, K., and Ishiguro, I. (1996). Conversion of gamma-glutamylcysteinylethyl ester to glutathione in rat hepatocytes. Biochim. Biophys. Acta 1313, 47-53.
39. Nishioka, M. C., Petersen, B. A., and Lewtas, J. (1982). Comparison of nitroaromatic content and direct-acting mutagenicity of diesel emissions. In Polynuclear Aromatic Hydrocarbons: Physical and Biological Chemistry. (M. Cooke, A. J. Dennis, and G. L. Fisher, Eds.), pp. 603-613. Battelle Press, Columbus, OH.
40. Omiecinski, C. J., Redlich, C. A., and Costa, P. (1990). Induction and developmental expression of cytochrome P4501A1 messenger RNA in rat and human tissues: Detection by the polymerase chain reaction. Cancer 50, 4315-4321.
41. Papac, D. I., and Franklin, M. R. (1988). N-Benzylimidazole, a high magnitude inducer of rat hepatic cytochrome P-450 exhibiting both polycyclic aromatic hydrocarbon-and phenobarbital-type induction of phase I and phase II drug-metabolizing enzymes. Drug. Metab. Disp. 16, 259-264.
42. Pumford, N. R., Martin, B. M., and Hinson, J. A. (1992). A metabolite of acetaminophen covalently binds to the 56 kDa selenium-binding protein. Biochem. Biophys. Res. Commun. 182, 1348-1355.
43. Schmeltz, I., Tosk, J., and Hoffman, D. (1976). Formation and determination of naphthalenes in cigarette smoke. Anal. Chem. 48, 645-650.
44. Slaughter, D. E., and Hanzlik, R. P. (1991). Identification of epoxide-and quinone-derived bromobenzene adducts to protein sulfur nucleophiles. Chem. Res.Toxicol. 4, 349-359.
45. Slaughter, D. E., Zheng, J., Harriman, S., and Hanzlik, R. P. (1993). Identification of covalent adducts to protein sulfur nucleophiles by alkaline permethylation. Anal. Biochem. 208, 288-295.
46. Stephen, F. D., Drahushuk, A. T., and Olson, J. R. (1997). Cytochrome P450 1A1 induction in rat lymphoid tissues following in viva and in vitro exposure to 2,3,7,8-tetrachlorodibenzo-p-dioxin requires protein kinase C. Toxicology 124, 39-51.
47. Tingle, M. D., Pirmohamed, M., Templeton, E., Wilson, A. S., Madden, S., Kitteringham, N. R., and Park, B. K. (1993). An investigation of the formation of cytotoxic, genotoxic, protein-reactive, and stable metabolites from naphthalene by human liver microsomes. Biochem. Pharmacol. 46, 1529-1538.
48. Van Winkle, L. S., Buckpitt, A. R., and Plopper, C. G. (1996). Maintenance of differentiated murine Clara cells in microdissected airway cultures. Am. J. Respir. Cell. Mol. Biol. 14, 586-598.
49. Warner, M., Hellmold, H., Magnusson, M., Rylander, T., Hedlund, E., and Gustafsson, J. (1998). Extrahepatic cytochrome P450: Role in in situ toxicity and cell-specific hormone sensitivity. Arch. Toxicol. 20(Suppl.), 455-463.
50. Wilson, A. S., Davis, C. D., Williams, D. P., Buckpitt, A. R., Pirmohamed, M., and Park, B. K. (1996). Characterization of the toxic metabolite(s) of naphthalene [published erratum appears in Toxicology 1997 120(1), 75]. Toxicology 114, 233-242.
51. Witschi, H. R., and Last, J. A. (1996). Toxic responses of the respiratory system. In Casarett & Doull's Toxicology: The Basic Science of Poisons (C. D. Klaassen, Ed.), pp. 443-462. McGraw-Hill, New York.
52. Young, L. (1947). The metabolic conversion of naphthalene to 1,2-dihydronaphthalene-1,2-diol. Biochem. J. 41, 417-422.
53. Zheng, J., Cho, M., Jones, A. D., and Hammock, B. D. (1997). Evidence of quinone metabolites of naphthalene covalently bound to sulfur nucleophiles of proteins of murine Clara cells after exposure to naphthalene. Chem. Res. Toxicol. 10, 1008-1014.