Mechanism of differential potencies of isothiocyanates as inducers of anticarcinogenic Phase 2 enzymes

Cancer Research

Volumn 58, Issue 20, 1998, Pages 4632-4639

  Zhang, Yuesheng ^a   Talalay, Paul ^a  

^a JOHNS HOPKINS UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 BENZENEDITHIOL ESTER; ANTINEOPLASTIC AGENT; BENZENE DERIVATIVE; BUTHIONINE SULFOXIMINE; CARCINOGEN; DITHIOCARBAMIC ACID; GLUTATHIONE; GLUTATHIONE TRANSFERASE; ISOTHIOCYANIC ACID DERIVATIVE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE DEHYDROGENASE (QUINONE); UNCLASSIFIED DRUG;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; AREA UNDER THE CURVE; ARTICLE; CELL VOLUME; CHEMICAL CARCINOGENESIS; CONTROLLED STUDY; DRUG ACCUMULATION; DRUG MECHANISM; DRUG POTENCY; DRUG STRUCTURE; DRUG UPTAKE; ENZYME INDUCTION; HEPATOMA CELL; HUMAN; HUMAN CELL; MOUSE; NONHUMAN; PRIORITY JOURNAL; RAT; TEMPERATURE DEPENDENCE;

ANIMALS; ANTICARCINOGENIC AGENTS; ENZYME INDUCTION; GLUCURONOSYLTRANSFERASE; GLUTATHIONE; GLUTATHIONE TRANSFERASE; ISOTHIOCYANATES; MICE; NAD(P)H DEHYDROGENASE (QUINONE); TUMOR CELLS, CULTURED;

EID: 0032532317     PISSN: 00085472     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (44)

1. Zhang, Y., and Talalay, P. Anticarcinogenic activities of organic isothiocyanates: chemistry and mechanisms. Cancer Res., 54 (Suppl.): 1976s-1981s, 1994.
2. Hecht, S. S. Chemoprevention by isothiocyanates. J. Cell Biochem. Suppl., 22: 195-209, 1995.
3. Prestera, T., Holtzclaw, W. D., Zhang, Y., and Talalay, P. Chemical and molecular regulation of enzymes that detoxify carcinogens. Proc. Natl. Acad. Sci. USA, 90: 2965-2969, 1993.
4. Smith, T. J., Hong, J. Y., Wang, Z. Y., and Yang, C. S. How can carcinogenesis be inhibited? Ann. NY Acad. Sci., 768: 82-90, 1995.
5. Primiano, T., Sutter, T. R., and Kensler, T. W. Antioxidant-inducible genes. Advan. Pharmacol., 38: 293-328, 1997.
6. Hecht, S. S. Approaches to cancer prevention based on an understanding of N-nitrosamine carcinogenesis. Proc. Soc. Exp. Biol. Med., 216: 181-191, 1997.
7. Kensler, T. W. Chemoprevention by inducers of carcinogen detoxification enzymes. Environ. Health Perspect., 105 (Suppl.): 964-970, 1997.
8. Yu, R., Mandlekar, S., Harvey, K. J., Ucker, D. S., and Kong, A-N. T. Chemopreventive isothiocyanates induce apoptosis and caspase-3-Iike activity. Cancer Res., 58: 402-408, 1998.
9. 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.
10. Milford, G. F. J., and Evans, E. F. Factors causing variation in glucosinolates in oil seed rape. Outlook Agric., 20: 31-37, 1991.
11. Mullin, W. J., and Sahasrabudhe, H. R. An estimate of the average daily intake of glucosinolates. Nutr. Rep. Int., 18: 273-279, 1978.
12. Fenwick, G. R., Heaney, P. K., and Mullin, W. J. Glucosinolates and their breakdown products in food and food plants. CRC Crit. Rev. Food Sci. Nutr., 18: 123-201, 1983.
13. Zhang, Y., Talalay, P., Cho, C-G., and Posner, G. H. A major inducer of anticarcinogenic protective enzymes from broccoli: isolation and elucidation of structure. Proc. Natl. Acad. Sci. USA, 89: 2399-2403, 1992.
14. Posner, G. H., Cho, C-G., Green, J. V., Zhang, Y., and Talalay, P. Design and synthesis of bifunctional isothiocyanate analogs of sulforaphane: correlation between structure and potency as inducers of anticarcinogenic detoxication enzymes. J. Med. Chem., 37: 170-176, 1994.
15. Kashfi, K., Zhang, Y., Yang, E. K., Talalay, P., and Dannenberg, A. J. Anticarcinogenic organic isothiocyanates induce UDP-glucuronosyltransferase. FASEB J., 9: A868, 1995.
16. Fahey, J. W., Zhang, Y., and Talalay, P. Broccoli sprouts: an exceptionally rich source of inducers of enzymes that protect against chemical carcinogens. Proc. Natl. Acad. Sci. USA, 94: 10367-10372, 1997.
17. Horoszewicz, J. S., Leong, S. S., Kawinski, E., Karr, J. P., Rosenthal, H., Chu, T. M., Mirand, E. A., and Murphy, G. P. LNCaP model of human prostatic carcinoma. Cancer Res., 43: 1809-1818, 1983.
18. Arbiser, J. L., Moses, M. A., Fernandez, C. A., Ghiso, N., Cao, Y., Klauber, N., Frank, D., Brownlee, M., Flynn, E., Parangi, S., Byers, H. R., and Folkman, J. Oncogenic H-ras stimulates tumor angiogenesis by two distinct pathways. Proc. Natl. Acad. Sci. USA, 94: 861-866, 1997.
19. Shantz, L. M., Talalay, P., and Gordon, G. B. Mechanism of inhibition of growth of 3T3-L1 fibroblasts and their differentiation to adipocytes by dehydroepiandrosterone and related steroids: role of glucose-6-phosphate dehydrogenase. Proc. Natl. Acad. Sci. USA, 86: 3852-3856, 1989.
20. Richler, C., and Yaffe, D. The in vitro cultivation and differentiation capacities of myogenic cell lines. Dev. Biol., 23: 1-22, 1970.
21. Hollenberg, M. D., and Cuatrecasas, P. Principles and techniques for the study of plasma membrane receptors related to hormone action. In: H. Busch (ed.), Methods in Cancer Res., Vol. XII, pp. 317-366. New York: Academic Press, 1976.
22. Zhang, Y., Cho, C-G., Posner, G. H., and Talalay, P. Spectroscopic quantitation of organic isothiocyanates by cyclocondensation with vicinal dithiols. Anal. Biochem., 205: 100-107, 1992.
23. Zhang, Y., Wade, K. L., Prestera, T., and Talalay, P. Quantitative determination of isothiocyanates, dithiocarbamates, carbon disulfide, and related thiocarbonyl compounds by cyclocondensation with 1,2-benzenedithiol. Anal. Biochem., 239: 160-167, 1996.
24. Smith, P. K., Krohn, R. I., Hermanson, G. T., Mallia, A. K., Gratner, F. H., Provenzano, M. D., Fujimoto, E. K., Goeke, N. M., Olson, B. J., and Klenk, D. C. Measurement of protein using bicinchoninic acid. Anal. Biochem., 150: 76-85, 1985.
25. Rocci, M. L., and Jusko, W. J. LAGRAN program for area and moments in pharmacokinetic analysis. Comput. Programs Biomed., 16: 203-216, 1983.
26. Ediss, C., and Tam, Y. K. An interactive computer program for determining areas bounded by drug concentration curves using Lagrange interpolation. J. Pharmacol. Toxicol. Methods, 34: 165-168, 1995.
27. Prochaska, H. J., and Santamaria, A. B. Direct measurement of NAD(P)H: quinone reductase from cells cultured in microtiter wells: a screening assay for anticarcinogenic enzyme inducers. Anal. Biochem., 169: 328-336, 1988.
28. Bradford, M. M. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem., 72: 248-254, 1976.
29. Hissin, P. J., and Hilf, R. Fluorometric method for determination of oxidized and reduced glutathione in tissues. Anal. Biochem. 74: 214-226, 1976.
30. Zhang, Y., Kolm, R. H., Mannervik, B., and Talalay, P. Reversible conjugation of isothiocyanates with glutathione catalyzed by human glutathione transferases. Biochem. Biophys. Res. Commun. 206: 748-755, 1995.
31. Kolm, R. H., Danielson, U. H., Zhang, Y., Talalay, P., and Mannervik, B. Isothiocyanates as substrates for human glutathione transferases: structure-activity studies. Biochem. J., 311: 453-459, 1995.
32. Meyer, D. J., Grease, D. J., and Ketterer, B. Forward and reverse catalysis and product sequestration by human glutathione S-transferases in the reaction of GSH with dietary aralkyl isothiocyanates. Biochem. J., J., 306: 565-569, 1995.
33. Bergelson, S., Pinkus, R., and Daniel, V. Intracellular glutathione levels regulate Fos/Jun induction and activation of glutathione S-transferase gene expression. Cancer Res., 54: 36-40, 1994.
34. 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.
35. 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.
36. Putzer, P. R., Zhang, Y., Prestera, T., Holtzclaw, W. D., Wade, K. L., and Talalay, P. Mercurials and dimercaptans: synergism in the induction of chemoprotective enzymes. Chem. Res. Toxicol., 8: 103-110, 1994.
37. Griffith, O. W., and Meister, A. Potent and specific inhibition of glutathione synthesis by buthionine sulfoximine (S-n-butyl homocysteine sulfoximine). J. Biol. Chem., 254: 7558-7560, 1979.
38. Anderson, M. E., Powrie, F., Puri, R. N., and Meister, A. Glutathione monoethyl ester: preparation, uptake by tissues, and conversion to glutathione. Arch. Biochem. Biophys., 239: 538-548, 1985.
39. Morse, M. A., Eklind, K. I., Hecht, S. S., Jordan, K. G., Choi, C-I., Desai, D. H., Amin, S. G., and Chung, F-L. Structure-activity relationship for inhibition of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone lung tumorigenesis by arylalkyl isothiocyanates in A/J mice. Cancer Res., 51: 1846-1850, 1991.
40. Zhang, Y., Kensler, T. W., Cho, C-G., Posner, G. H., and Talalay, P. Anticarcinogenic activities of sulforaphane and structurally related synthetic norbornyl isothiocyanates. Proc. Natl. Acad. Sci. USA, 91: 3147-3150, 1994.
41. Jiao, D., Eklind, K. I., Choi, C. I., Desai, D. H., Amin, S. G., and Chung, F-L. Structure-activity relationships of isothiocyanates as mechanism-based inhibitors of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone-induced lung tumorigenesis in A/J mice. Cancer Res., 54: 4327-4333, 1994.
42. Wilkinson, J. T., Morse, M. A., Kresty, L. A., and Stoner, G. D. Effect of alkyl chain length on inhibition of N-nitromethylbenzylamine-induced esophageal tumorigenesis and DNA methylation by isothiocyanates. Carcinogenesis (Lond.), 16: 1011-1015, 1995.
43. Ishikawa, T. The ATP-dependent glutathione S-conjugate export pump. Trends Biochem. Sci., 17: 463-468, 1992.
44. Jedlitschky, G., Leier, I., Buchholz, U., Barnouin, K., Kurz, G., and Keppler, D. Transport of glutathione, glucuronate, and sulfate conjugates by MRP gene-encoded conjugate export pump. Cancer Res., 56: 988-994, 1996.