Redox regulation of glutathione S-transferase induction by benzyl isothiocyanate: Correlation of enzyme induction with the formation of reactive oxygen intermediates

Cancer Research

Volumn 60, Issue 2, 2000, Pages 219-225

  Nakamura, Yoshimasa ^a   Ohigashi, Hajime ^a   Masuda, Seiji ^a   Murakami, Akira ^b   Morimitsu, Yasujiro ^d   Kawamoto, Yoshiyuki ^d   Osawa, Toshihiko ^d   Imagawa, Masayoshi ^c   Uchida, Koji ^a,d  

^a KYOTO UNIVERSITY   (Japan)

^b KINKI UNIVERSITY   (Japan)

^c OSAKA UNIVERSITY   (Japan)

^d NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BENZYL ISOTHIOCYANATE; GLUTATHIONE TRANSFERASE; ISOENZYME; MALEIC ACID DIETHYL ESTER; REACTIVE OXYGEN METABOLITE;

ANIMAL CELL; ANIMAL EXPERIMENT; ARTICLE; CHEMOPROPHYLAXIS; CONTROLLED STUDY; ENZYME ACTIVITY; ENZYME INDUCTION; FLUORESCENCE; GENE INDUCTION; IMMUNOBLOTTING; NONHUMAN; NORTHERN BLOTTING; OXIDATION REDUCTION REACTION; PRIORITY JOURNAL; RAT;

ANIMALS; CELL LINE; CHLORAMPHENICOL O-ACETYLTRANSFERASE; DNA PROBES; ENZYME INDUCTION; GLUTATHIONE TRANSFERASE; ISOTHIOCYANATES; KINETICS; LIVER; OXIDATION-REDUCTION; RATS; REACTIVE OXYGEN SPECIES; RECOMBINANT FUSION PROTEINS; TRANSFECTION;

EID: 0034650803     PISSN: 00085472     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (51)

1. Wattenberg, L. W. Inhibition of carcinogen-induced neoplasia by sodium cyanate, tert-butyl isocyanate and benzyl isothiocyanate administered subsequent to carcinogen exposure. Cancer Res., 41: 2991-2994, 1981.
2. Wattenberg, L. W. Inhibitory effects of benzyl isothiocyanate administered shortly before diethylnitrosamine or benzo(a)pyrene on pulmonary and forestomach neoplasia in A/J mice. Carcinogenesis (Lond.), 8: 1971-1973, 1987.
3. Morse, M. A., Zu, H., Galati, A. J., Schmidt, C. J., and Stoner, G. D. Dose-related inhibition by dietary phenethylisothiocyanate of esophageal tumorigenesis and DNA methytation induced by N-nitrosomethylbenzylamine in rats. Cancer Lett., 72: 103-110, 1993.
4. Stoner, G. D., Morrissey, D. T., Heur, Y. H., Daniel, E. M., Galati, A. J., and Wagner, S. A. Inhibitory effects of phenethylisothiocyanate on N-nitrosobenzylmethylamine carcinogenesis in the rat esophagus. Cancer Res., 51: 2063-2068, 1991.
5. Hecht, S. S. Chemoprevention by isothiocyanates. J. Cell. Biochem. Suppl., 22: 195-209, 1995.
6. Talalay, P. Mechanisms of enzymes that protect against chemical carcinogenesis. Adv. Enzyme Regul., 28: 237-250, 1989.
7. Guo, Z., Smith, T. J., Wang, E., Eklind, K., Chung, F-L., and Yang, C. S. Structure-activity relationships of arylalkyl isothiocyanates for the inhibition of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone metabolism and the modulation of xenobiotic-metabolizing enzymes in rats and mice. Carcinogenesis (Lond.), 14: 1167-1173, 1993.
8. Morse, M. A., and Stoner, G. D. Cancer chemoprevention: principles and prospects. Carcinogenesis (Lond.), 14: 1737-1746, 1993.
9. Fukuda, A., Nakamura, Y., Ohigashi, H., Osawa, T., and Uchida, K. Cellular response to the redox active lipid peroxidation products: induction of glutathione S-transferase P by 4-hydroxy-2-nonenal. Biochem. Biophys. Res. Commun., 236: 505-509, 1997.
10. Uchida, K., Shiraishi, M., Naito, Y., Torii, Y., Nakamura, Y., and Osawa, T. Activation of stress signaling pathways by the end product of lipid peroxidation. 4-Hydroxy-2-nonenal is a potential inducer of intracellular peroxide production. J. Biol. Chem., 274; 2234-2242, 1999.
11. Pinkus, R., Weiner, L. M., and Daniel, V. Role of quinone-mediated generation of hydroxyl radicals in the induction of glutathione S-transferase gene expression. Biochemistry, 34: 81-88, 1995.
12. Pinkus, R., Weiner, L. M., and Daniel, V. Role of oxidants and antioxidants in the induction of AP-1, NF-κB, and glutathione S-transferase gene expression. J. Biol. Chem., 271: 13422-13429, 1996.
13. Chen, Y-R., Wang, W., Kong, A-N. T., and Tan, T-H. Molecular mechanisms of c-Jun N-terminal kinase-mediated apoptosis induced by anticarcinogenic isothiocyanates. J. Biol. Chem., 273: 1769-1775, 1998.
14. Yamada, M., Okigaki, T., and Awai, M. Adhesion and growth of rat liver epithelial cells on an extracellular matrix with proteins from fibroblast conditioned medium. Cell Struct. Funct., 12: 53-62, 1987.
15. Habig, W. H., Pabst, M. J., and Jakoby, W. B. Glutathione S-transferase. The first enzymatic step in mercapturic acid formation. J. Biol. Chem., 249: 7130-7139, 1974.
16. Laemmuli, U. K. Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature (Lond.), 227: 680-685, 1970.
17. Sugioka, Y., Fujii-Kuriyama, Y., Kitagawa, T., and Muramatsu, M. Cloning and the nucleotide sequence of rat glutathione S-transferase P cDNA. Nucleic Acids Res., 13: 6049-6057, 1985.
18. Fukuda, A., Osawa, T., Oda, H., Toyokuni, S., Satoh, K., and Uchida, K. Oxidative stress response in iron-induced renal carcinogenesis: acute nephrotoxicity mediates the enhanced expression of glutathione S-transferase Yp isozyme. Arch. Biochem. Biophys., 329: 39-46, 1996.
19. Bass, D. A., Parce, J. W., Dechatelet, L. R., Szejda, P., Seeds, M. C., and Thomas, M. Flow cytometric studies of oxidative product formation by neutrophils: a graded response to membrane stimulation. J. Immunol., 130: 1910-1917, 1983.
20. Nakamura, Y., Murakami, A., Ohto, Y., Torikai, K., Tanaka, T., and Ohigashi, H. Suppression of tumor promoter-induced oxidative stress and inflammatory responses in mouse skin by a superoxide generation inhibitor 1′-acetoxychavicol acetate. Cancer Res., 58: 4832-4839, 1998.
21. Sakai, M., Okuda, A., and Muramatsu, M. Multiple regulatory elements and phorbol 12-O-tetradecanoale 13-acetate responsiveness of the rat placental glutathione transferase gene. Proc. Natl. Acad. Sci. USA, 85: 9456-9460, 1988.
22. Chen, C., and Okayama, H. High-efficiency transformation of mammalian cells by plasmid DNA. Mol. Cell. Biol., 7: 2745-2752, 1987.
23. Sparnins, V. L., and Wattenberg, L. W. Enhancement of glutathione S-transferase activity of the mouse forestomach by inhibitors of benzo(a)pyrene-induced neoplasia of the forestomach. J. Natl. Cancer Inst., 66: 769-772, 1981.
24. Vos, R. M. E., Snoek, M. C., van Berkel, W. J. H., Mueller, F., and van Bladeren, P. J. Differential induction of rat hepatic glutathione S-transferase isoenzymes by hexachlorobenzene and benzyl isothiocyanate: comparison with induction by phenobarbital and 3-methylcholanthrene. Biochem. Pharmacol., 37: 1077-1082, 1988.
25. Henderson, C. J., Smith, A. G., Ure, J., Brown, K., Bacon, E. J., and Wolf, C. R. Increased skin tumorigenesis in mice lacking pi class glutathione S-transferases. Proc. Natl. Acad. Sci. USA, 95: 5275-5280, 1998.
26. Shi, M. M., Kugelman, A., Iwamoto, T., Tian, L., and Forman, H. J. Quinone-induced oxidative stress elevates glutathione and induces γ-glutamylcysteine synthetase activity in rat lung epithelial L2 cells. J. Biol. Chem., 269: 26512-26517, 1994.
27. Lautier, D., Luscher, P., and Tyrrell, R. M. Endogenous glutathione levels modulate both constitutive and UVA radiation-hydrogen peroxide inducible expression of the human heme oxygenase gene. Carcinogenesis (Lond.), 13: 227-232, 1992.
28. Fukuda, A., Osawa, T., Oda, H., Tanaka, T., Toyokuni, S., and Uchida, K. Oxidative stress response in iron-induced acute nephrotoxicity: enhanced expression of heat shock protein 90. Biochem. Biophys. Res. Commun., 219: 76-81, 1996.
29. Rosette, C., and Karin, M. Ultraviolet light and osmotic stress: activation of the JNK cascade through multiple growth factor and cytokine receptors. Science (Washington DC), 274: 1194-1197, 1996.
30. Galcheva-Gargova, Z., Derijard, B., Wu, J-H., and Davis, R. J. An osmosensing signal transduction pathway in mammalian cells. Science (Washington DC), 265: 806-808, 1994.
31. Kharbanda, S., Ren, R., Pandey, P., Shafman, T. D., Feller, S. T., Weichselbaum, R. R., and Kufe, D. W. Activation of the c-Abl tyrosine kinase in the stress response to DNA-damaging agents. Nature (Lond.), 376: 785-788, 1995.
32. Sluss, H. K., Barrett, T., Derijard, B., and Davis, R. J. Signal transduction by tumor necrosis factor mediated by JNK protein kinases. Mol. Cell. Biol., 14: 8376-8384, 1994.
33. Zhang, Y., and Talalay, P. Mechanism of differential potencies of isothiocyanates as inducers of anticarcinogenic phase 2 enzymes. Cancer Res., 58: 4632-4639, 1998.
34. Catheart, R., Schwiers, E., and Ames, B. N. Detection of picomole levels of hydroperoxides using a fluorescent dichlorofluorescein assay. Anal. Biochem., 134: 111-116, 1983.
35. Crow, J. P. Dichlorodihydrofluorescein and dihydrorhodamine 123 are sensitive indicators of peroxynitrite in vitro: implications for intracellular measurement of reactive nitrogen and oxygen species. Nitric Oxide. Biol. Chem., 1: 145-157, 1997.
36. Yamada, M., Okigaki, T., and Awai, M. Role of superoxide radicals in cytotoxic effects of Fe-NTA on cultured normal liver epithelial cells. Cell Struct. Funct. 12: 407-420, 1987.
37. McCord, J. M. Oxygen-derived free radicals in postischemic tissue injury. N. Engl. J. Med., 312: 159-163, 1985.
38. Reed, D. J. Glutathione: toxicological implications. Annu. Rev. Pharmacol. Toxicol., 30: 603-631, 1990.
39. Shrieve, D. C., Bump, E. A., and Rice, G. C. Heterogeneity of cellular glutathione among cells derived from a murine fibrosarcoma or a human renal cell carcinoma detected by flow cytometric analysis. J. Biol. Chem., 263: 14107-14114, 1988.
40. Cross, A. R., and Jones, O. T. G. The effect of the inhibitor diphenyleneiodonium on the superoxide-generating system of neutrophils: specific labeling of a component polypeptide of the oxidase. Biochem. J., 237: 111-116, 1986.
41. Li, Y., and Trush, M. A. Diphenyleneiodonium, an NAD(P)H oxidase inhibitor, also potently inhibits mitochondrial reactive oxygen species production. Biochem. Biophys. Res. Commun., 253: 295-299, 1998.
42. Livingstone, C., Patel, G., and Jones, N. ATF-2 contains a phosphorylation-dependent transcriptional activation domain. EMBO J., 14: 1785-1797, 1995.
43. Gupta, S., Campbell, D., Derijard, B., and Davis, R. J. Transcription factor ATF2 regulation by the JNK signal transduction pathway. Science (Washington DC), 267: 389-393, 1995.
44. Cavigelli, M., Dolfi, F., Claret, F-X., and Karin, M. Induction of c-fos expression through JNK-mediated TCF/Elk-1 phosphorylation. EMBO J., 14: 5957-5964, 1995.
45. Whitmarsh, A. J., Shore, P., Sharrocks, A. D., and Davis, R. J. Integration of MAP kinase signal transduction pathways at the serum response element. Science (Washington DC), 269: 403-407, 1995.
46. Adler, V., Yin, Z., Fuchs, S. Y., Benezra, M., Rosario, L., Tew, K. D., Pincus, M. R., Sardana, M., Henderson, C. J., Wolf, C. R., Davis, R. J., and Ronai, Z. Regulation of JNK signaling by GSTp. EMBO J., 18: 1321-1334, 1999.
47. Ogawa, K., Futakuchi, M., Hirose, M., Boonyaphiphat, P., Mizoguchi, Y., Miki, T., and Shirai, T. Stage and organ dependent effects of 1-O-hexyl-2,3,5-trimethylhydroquinone, ascorbic acid derivatives, N-heptadecane-8,10-dione and phenylethyl isothiocyanate in a rat multiorgan carcinogenesis model. Int. J. Cancer, 76: 851-856, 1998.
48. Hirose, M., Yamaguchi, T., Kimoto, N., Ogawa, K., Futakuchi, M., Sano, M., and Shirai, T. Strong promoting activity of phenylethyl isothiocyanate and benzyl isothiocyanate on urinary bladder carcinogenesis in F344 male rats. Int. J. Cancer, 77: 773-777, 1998.
49. Lee, M-S. Enzyme induction and comparative oxidative desulfuration of isothiocyanates to isocyanates. Chem. Res. Toxicol., 9: 1072-1078, 1996.
50. Caspary, W. J., and Myhr, B. Mutagenicity of methylisocyanate and its reaction products to cultured mammalian cells. Mutat. Res., 174: 285-293, 1986.
51. Bruggeman, I. M., Temmink, J. H. M., and van Bladeren, P. J. Glutathione- and cysteine-mediated cytotoxicity of allyl and benzyl isothiocyanate. Toxicol. Appl. Pharm., 83: 349-359, 1986.