Inhibition of N-nitrosodimethylamine demethylase in rat and human liver microsomes by isothiocyanates and their glutathione, L-cysteine, and N- acetyl-L-cysteine conjugates

Chemical Research in Toxicology

Volumn 9, Issue 6, 1996, Pages 932-938

  Jiao, Ding ^a   Clifford Conaway, C ^a   Wang, Mong Heng ^b   Yang, Chung S ^b   Koehl, Werner ^a,c   Chung, Fung Lung ^a  

^a AMERICAN HEALTH FOUNDATION   (United States)

^b RUTGERS UNIVERSITY   (United States)

^c Rheinland Pfälzische Technische Universität Kaiserslautern Landau   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CYSTEINE; DIMETHYLNITROSAMINE DEMETHYLASE; GLUTATHIONE; ISOCYANIC ACID DERIVATIVE; NITROSAMINE;

ANIMAL TISSUE; ARTICLE; CHEMICAL CARCINOGENESIS; ENZYME INHIBITION; LIVER MICROSOME; LUNG CANCER; NONHUMAN; RAT;

ACETYLCYSTEINE; ANIMALS; CYSTEINE; CYTOCHROME P-450 CYP2E1; DOSE-RESPONSE RELATIONSHIP, DRUG; GLUTATHIONE; HUMANS; ISOTHIOCYANATES; KINETICS; MALE; MICROSOMES, LIVER; RATS; RATS, INBRED F344;

EID: 9544258372     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx9502094     Document Type: Article

References (43)

1. Wattenberg, L. W. (1978) Inhibition of carcinogenic effects of polycyclic hydrocarbons by benzyl isothiocyanate and related compounds. J. Natl. Cancer Inst. 58, 395-398.
2. Wattenberg, L. W. (1987) Inhibitory effects of benzyl isothiocyanate administered shortly before diethylnitrosamine or benzo(a)pyrene on pulmonary and forestomach neoplasia in A/J mice. Carcinogenesis (London) 8, 1971-1973.
3. Morse, M. A., Wang, C-X., Stoner, G. D., Mandal, S., Conran, P. B., Amin, S. G., Hecht, S. S., and Chung, F.-L. (1989) Inhibition of 4-(methylnitrosamino)-l-(3-pyridyl)-l-butanone-induced DNA adduct formation and tumorigenicity in the lung of F344 rats by dietary phenethyl isothiocyanate. Cancer Res. 49, 549-553.
4. Chung, F.-L. (1992) Chemoprevention of lung carcinogenesis by aromatic isothiocyanates. In Cancer Chemoprevention Wattenberg, L., Lipkin, M., Boone, C. W., and Kelloff, G. J., Eds.) pp 227-245, CRC Press, Boca Raton, FL.
5. Stoner, G. D., Morrissey, D. T., Heur, Y.-H., Daniel, E. M., Galati, A. J., and Wagner, S. A. (1991) Inhibitory effects of phenethyl isothiocyanate on N-nitrosobenzylmethylamine carcinogenesis in rat esophagus. Cancer Res. 51, 2063-2068.
6. Adam-Rodwell, G., Morse, M. A., and Stoner, G. D. (1993) The effects of phenethyl isothiocyanate on benzofalpyrene-induced tumors and DNA adducts in A/J mouse lung. Cancer Lett. 71, 35-42.
7. 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. (1991) Structure-activity relationships for inhibition of 4-(methylnitrosamino)-l-(3-pyridyl)-1-butanone lung tumorigenesis by arylalkyl isothiocyanates in A/J mice. Cancer Res. 51, 1846-1850.
8. Smith, T. J., Guo, Z., Thomas, P. E., Chung, F.-L., Morse, M. A., Eklind, K., and Yang, C. S. (1990) Metabolism of 4-(methylnitrosamino)-l-(3-pyridyl)-l-butanone in mouse lung microsomes and its inhibition by isothiocyanates. Cancer Res. 50, 6817-6822.
9. Guo, Z., Smith, T. J., Wang, E., Sadrieh, N., Ma, Q., Thomas, P. E., and Yang, C. S. (1992) Effects of phenethyl isothiocyanate, a carcinogenesis inhibitor, on xenobiotic-metabolizing enzymes and nitrosamine metabolism in rats. Carcinogenesis 13, 2205-2210.
10. Guo, Z., Smith, T. J., Wang, E., Eklind, K. I., Chung, F.-L., and Yang, C. S. (1993) Structure-activity relationships of arylalkyl isothiocyanates for the inhibition of 4-(methylnitrosamino)-l-(3-pyridyD-1-butanone: metabolism and the modulation of xenobiotic-metabolizing enzymes in rats and mice. Carcinogenesis 14, 1167-1173.
11. Chung, F.-L., Wang, M., and Hecht, S. S. (1985) Effects of dietary indoles and isothiocyanates on N-nitrosodimethylamine and 4-(methylnitrosamino)-l-(3-pyridyl)-l-butanone α-hydroxylation and DNA methylation in rat liver. Carcinogenesis 6, 539-543.
12. Magee, P. N., Montesano, P., and Preussmann, R. (1976) N-Nitroso compounds and related carcinogens. In Chemical Carcinogens (Searle, C. E., Ed.) American Chemical Society Monograph 173, pp 491-625, American Chemical Society, Washington, DC.
13. Hoffmann, D., Djordjevic, M. V., Rivenson, A., Zang, E., Desai, D. and Amin, S. (1993) A study of tobacco carcinogenesis. LI. Relative potencies of tobacco-specific N-nitrosamines as inducers of lung tumours in A/J mice. Cancer Lett. 71, 25-30.
14. Yang, C. S., Yoo, J.-S. H., Ishizaki, H., and Hong, J. (1990) Cytochrome P450IIE1: roles in nitrosamine metabolism and mechanisms of regulation. Drug Metab. Rev. 22 (2 and 3), 147-159.
15. Ishizaki, H., Frady, J. F., Ning, S. M., and Yang, C. S. (1990) Effect of phenethyl isothiocyanate on microsomal N-nitrosodimethylamine metabolism and other monooxygenase activities, Xenobiotica 20 (3), 255-264.
16. Brüsewitz, G., Cameron, B. D., Chasseaud, L. F., Görler, K., Hawkins, D. R., Koch, H., and Mennicke, W. H. (1977) The metabolism of benzyl isothiocyanate and its cysteine conjugate. Biochem. J. 162, 99-107.
17. Eklind, K. I., Morse, M. A., and Chung, F.-L. (1990) Distribution and metabolism of the natural anticarcinogen phenethyl isothiocyanate in A/J mice. Carcinogenesis 11, 2033-2036.
18. Chung, F.-L., Morse, M. A., Eklind, K. I., and Lewis, J. (1992) Quantitation of human uptake of the anticarcinogen phenethyl isothiocyanate after a watercress meal. Cancer Epidemiol. Biomarkers Prev. 1, 383-388.
19. Jiao, D., Ho, C.-T., Foiles, P., and Chung, F.-L. (1994) Identification and quantitation of N-acetylcysteine conjugate of allyl isothiocyanate in human urine after ingestion of mustard. Cancer Epidemiol., Biomarkers Prev. 3, 487-492.
20. Bruggeman, I. M., Temmink, J. H. M., and van Bladeren, P. J. (1986) Glutathione- and cysteine-mediated cytotoxicity of allyl and benzyl isothiocyanate, Toxicol. Appl. Pharmacol. 83, 349-359.
21. Aue, W. P., Bartholdi, E., and Ernst, R. R. (1976) Two-dimensional spectroscopy: Application to nuclear magnetic resonance. J. Chem. Phys. 64, 2229-2246.
22. Nagayama, K., Kumar, A., Wuthrich, K., and Ernst, R. R. (1980) Experimental techniques of two-dimensional correlated spectroscopy. J. Magn. Reson. 40, 321-334.
23. Gizzle, W. E., and Polt, S. S. (1988) Guidelines to avoid personnel contamination by infective agents in research laboratories that use human tissues. J. Tissue Culture Methods 11 (4), 191-199.
24. Hecht, S. S., Chen, C. B., and Hoffmann, D. (1978) Evidence for metabolic α-hydroxylation of N-nitrosopyrrolidine. Cancer Res. 38, 215-218.
25. Wang, P. P., Beaune, P., Kaminsky, L. S., Dannan, G. A., Kadlubar, F. F., Larrey, D., and Guengerich, F. P. (1983) Purification and characterization of six cytochrome P-450 isozymes from human liver microsomes. Biochemistry 22, 5375-5383.
26. Bradford, M. M. (1976) 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.
27. Yang, C. S., Patten, C., J., Ishizaki, H., Yoo, J.-S. H. (1991) Induction, purification, and characterization of cytochrome P450IIE. Methods Enzymol. 206, 595-603.
28. Yoo, J.-S. H., Yheung, R., J., Patten, C. J., Wade, D., and Yang, C. S. (1987) Nature of N-nitrosodimethylamine demethylase and its inhibitors. Cancer Res. 47, 3378-3383.
29. Zhang, Y., Talalay, P., Cho, C.-G., and Posner, G. H. (1992) A major inducer of anticarcinogenic protective enzymes from broccoli: Isolation and elucidation of structure. Proc. Natl. Acad. Sci. U.S.A. 89, 2399-2403.
30. Bogaards, J. J., van Ommen, B., Falke, H. E., Willems, M. I., and van Bladeren, P. J. (1990) Glutathione S-transferase subunit induction patterns of Brussels sprouts, allyl isothiocyanate and goitrin in rat liver and small intestinal mucosa: a new approach for the identification of inducing xenobiotics. Food Chem. Toxicol. 28, 81-88.
31. Hara, A., Sakai, N., Yamada, H., Tanaka, T., Kato, K., Mori, H., and Sato, K. (1989) Induction of glutathione S-transferase, placental type in T9 glioma cells by dibutyryladenosine 3′,5′-cyclic monophosphate and modification of its expression by naturally occurring isothiocyanates. Acta Neuropathol. 79, 144-148.
32. Chung, F.-L., Morse, M. A., and Eklind, K. I. (1992) New potential chemopreventive agents for lung carcinogenesis of tobacco-specific nitrosamine. Cancer Res. (Suppl.) 52, 2719s-2722s.
33. Yamazaki, H., Inui, Y., Yun, C.-H., Guengerich, F. P., and Shimada, T. (1992) Cytochrome P450 2E1 and 2A6 enzymes as major catalysts for metabolic activation of N-nitrosodialkylamines and tobacco-related nitrosamines in human liver microsomes. Carcinogenesis 13, 1789-1794.
34. Camus, A.-M., Geneste, O., Honkakoski, P., Bereziat, J.-C., Henderson, C. J., Wolf, C. R., Bartsch, H., and Lang, M. A. (1993) High variability of nitrosamine metabolism among individuals: role of cytochromes P450 2A6 and 2E1 in the dealkylation of N-nitrosodimethylamine and N-nitrosodiethylamine in mice and humans. Mol. Carcinogen. 7, 268-275.
35. Drobnica, L., Kristian, P., and Augustin, J. (1977) The chemistry of the -NCS group. In The Chemistry of Cyanates and Their Thio Derivatives (Patai, S., Ed.) Part 2, pp 1003-1221, Wiley, New York.
36. Smith, T. J., Guo, Z., Li, C., Ning, S. M., Thomas, P. E., and Yang, C. S. (1993) Mechanisms of inhibition of 4-(methylnitrosamino)-1-(3-pyridyl)-l-butanone bioactivation in mouse by dietary phenethyl isothiocyanate. Cancer Res. 53, 3276-3282.
37. Jiao, D., Eklind, K. I., Desai, D. H., Amin, S. G., Choi, C.-I., and Chung, F.-L. (1994) Structure-activity relationships of isothiocyanates as mechanism-based inhibitors of 4-(methylnitrosamino)-1-(3-pyridyl)-l-butanone-induced lung tumorigenesis in A/J mice. Cancer Res. 54, 4327-4333.
38. Song, B. J., Gelboin, H. V., Park, S. S., Yang, C. S., and Gonzalez, F. J. (1986) Complementary DNA and protein sequences of ethanol-inducible rat and human cytochrome P-450s. J. Biol. Chem. 261, 16689-16697.
39. Yang, C. S. (1975) The association between cytochrome P-450 and NADPH-cytochrome P-450 reductase in microsomal membrane. FEES Lett. 54, 61-64.
40. Zhang, Y., Kolm, R. H., Mannervik, B., and Talalay, P. (1995) Reversible conjugation of isothiocyanates with glutathione catalyzed by human glutathione transferases. Biochem. Biophys. Res. Commun. 206, 748-755.
41. Meyer, D. J., Crease, D. J., and Ketterer, B. (1995) Forward and reverse catalysis and sequestration by human glutathione S-transferases in the reaction of GSH with dietary aralkyl isothiocyanates. Biochem. J. 306, 565-569.
42. Baillie, T. A., and Slatter, J. G. (1991) Glutathione: a vehicle for the transport of chemically reactive metabolites in vivo. Acc. Chem. Res. 24, 264-270.
43. Zheng, G., Kenney, P. M., and Lam, L. K. T. (1992) Phenylalkyl isothiocyanate-cysteine conjugates as glutathione S-transferase stimulating agents. J. Med. Chem. 35, 185-188.