Publication Cover
Xenobiotica
the fate of foreign compounds in biological systems
Volume 30, 2000 - Issue 5
46
Views
15
CrossRef citations to date
0
Altmetric
Research Article

Effects of phenethylisothiocyanate on the expression of glutathione S-transferases and hepatotoxicity induced by acetaminophen

, , , &
Pages 535-545 | Published online: 22 Sep 2008

References

  • AMES, B. N., 1983, Dietary carcinogens and anticarcinogens. Science, 221, 1256–1264.
  • BOYD, E. M. and BERECZKY, G. M., 1966, Liver necrosis from paracetamol. British Journal of Pharmacology and Chemotherapy, 26, 606–614.
  • CARR, B. I., 1985, Chemical carcinogens and inhibitors of carcinogenesis in the human diet. Cancer, 55, 218–224.
  • CATHALA, G., SAVOURET, J.-F., MENDEZ, B., WEST, B. L., KARIN, M., MARTIAL, J. A. and BAXTER, J. D., 1983, Laboratory methods; A method for isolation of intact, translationally active ribonucleic acids. DNA, 2, 329–335.
  • CHALKLEY, H. W., 1943, Methods for the quantitative morphologic analysis of tissues. Journal of National Cancer Institute, 4, 47–53.
  • CHOMCZYNSKI, P. and SACCHI, N., 1987, Single-step method of RNA isolation by acid guanidinium thiocyanate—phenol—chloroform extraction. Analytical Biochemistry, 162, 156–159.
  • COLDWELL, B. B., THOMAS, B. H., WortmousE, L. W., WONG, L. T. and HYNIE, I., 1976, Metabolism of 14C-acetaminophen in humans and laboratory animals. Proceedings of the Society of Environmental Toxicology, 17, 269–276.
  • CORCORAN, G. B., MITCHELL, J. R., VAISHNAV, Y. N. and HORNING, E. C., 1980, Evidence that acetaminophen and N-hydroxyacetaminophen form a common arylating intermediate, N-acetyl-p-benzoquinoneimine. Molecular Pharmacology, 18, 536–542.
  • DAHLIN, D. C., MrwA, G. T., Lu, A. Y. H. and NELSON, S. D., 1984, N-acetyl-p-benzoquinoneimine; A cytochrome P450-mediated oxidation product of acetaminophen. Proceedings of the National Academy of Sciences, USA, 81, 1327–1331.
  • DAVIDSON, D. G. and EASTHAM, W. N., 1966, Acute liver necrosis following overdose of paracetamol. British Medical Journal, 2, 497–499.
  • DAVIS, D. C., POTTER, W. Z., JOLLOW, D. J. and MITCHELL, J. R., 1974, Species differences in hepatic glutathione depletion, covalent binding and hepatic necrosis after acetaminophen. Life Science, 14, 2099–2109.
  • DAVIS, I. G., DIENER, M. D. and BATTERY, J. F., 1989, Western blot analysis. In Basic Methods in Molecular Biology (New York: Elsevier), pp. 311–314.
  • DOERR-O'ROURKE, K., TRUSHIN, N., HECHT, S. S. and STONER, G. D., 1991, Effect of phenethyl isothiocyanate on the metabolism of the tobacco-specific nitro samine 4-(methylnitroamino) -1 -(3 - pyridy1)-1 -butanone by cultured rat lung tissue. Carcinogenesis, 12, 1029–1034.
  • GREGUS, Z., MADHU, C. and KLAASSEN, C. D., 1988, Species variation in toxication and detoxication of acetaminophen in vivo; a comparative study of biliary and urinary excretion of acetaminophen metabolites. Journal of Pharmacology and Experimental Therapeutics, 244, 91–99.
  • Guo, Z., SMITH, T. J., THOMAS, P. E. and YANG, C. S., 1991, Metabolic activation of 4-(methyl-nitrosamine)-1-(3-pyridy1)-1-butanone as measured by DNA alltylation in vitro and its inhibition by isothiocyanates. Cancer Research, 51, 4798–4803.
  • Guo, Z., Sisirto, T. J., WANG, E., EKLIND, K. I., CHUNG, F.-L. and YANG, F. S., 1993, Structure—activity relationships of arylalkyl isothiocyanates for the inhibition of 4-(methylnitrosamino) -143-pyridy1)-1 -butanone metabolism and the modulation of xenobiotic-metabolizing enzymes in rats and mice. Carcinogenesis, 14, 1167–1173.
  • Guo, Z., SMITH, T. J., WANG, E., SADRICH, N., MA, Q., THOMAS, P. E. and YANG, C. S., 1992, Effects of phenylhexyl isothiocyanate, a carcinogenesis inhibitor, on xenobiotic -metabolizing enzymes and nitrosamine metabolism in rats. Carcinogenesis. 13, 2205–2210.
  • HABIG, W. H., PABST, M. J. and JAKOBY, W. B., 1974, Glutathione S-transferase; the first enzymatic step in mercapturic acid formation. Journal of Biological Chemistry, 249, 7130–7139.
  • HARVISON, P. J., GUENGERICH, F. P., RASHED, M. S. and NELAON, S. D., 1988, Cytochrome P450 isozymes selectivity in the oxidation of acetaminophen. Chemical Research in Toxicology, 1, 47–52.
  • HAYATSU, H., AIUMOTO, S. and NEGISHE, T., 1988, Dietary inhibitors of mutagenesis and carcinogenesis. Mutation Research, 202, 429–446.
  • HAYES, J. D. and PULP:MD, D. J., 1995, The glutathione S-transferase supergene family. Regulation of GST and the contribution of the isoenzymes to cancer chemoprotection and drug resistance. Critical Reviews in Biochemistry and Molecular Biology, 30, 445–600.
  • HAZELTON, G. A., HJELLE, J. J. and KLAASSEN, C. D., 1986, Effect of cysteine pro-drugs on acetaminophen -induced hepatotoxicity. Journal of Pharmacology and Experimental Therapeutics, 237, 341–349.
  • HEAGERTY, A. H. M., FITZGERALD, D., Swill, A., BOWERS, B., Jos, P., FRYER, A., ZHAO, ALLDERSEA, J. and STRANGE, R. C., 1994, Glutathione S-transferase GSTM1 phenotypes and protection against cutaneous malignancy. Lancet, 343, 266–268.
  • HINSON, J. A., 1982, Biochemical toxicology of acetaminophen. In E. Hodgson, J. R. Bend and R. M. Philpot (eds), Reviews in Biochemical Toxicology (New York: Elsevier/North Holland), pp. 103–109.
  • HOWIE, D., ADRIAENSSENS, P. and PRESCOTT, L. F., 1977, Paracetamolmetabolism following overdosage; application of high performance liquid chromatography. Journal of Pharmacy and Pharmacology, 29, 235–237.
  • HUSSEY, A. J. and HAYES, J. D. H., 1993, Human µ-class glutathione S-transferases present in liver, skeletal muscle and testicular tissue. Biochimica et Biophysica Acta, 1203, 131–141.
  • JACOBSON, A., 1987, Purification and fractionation of poly(A)± RNA. Methods in Enzymology, 152, 254–261.
  • JOLLOW, D. J., ROBERTS, S., PRICE, V. and SMOTH, C., 1982, Biochemical basis for dose response relationships in reactive intermediate toxicity. In R. Snyder, D. V. Parke, J. J. Kocois, G. Gibson and D. J. Jollow (eds), Biological Reactive Intermediates. II: Chemical Mechanisms and Biological Effects (New York: Plenum), pp. 99-113.
  • JOLLOW, D. J., THORGE1RSSON, S. S., POTIER, W. Z., HASHIMOTO, M. and MITCHELL, J. R., 1974, Acetaminophen-induced hepatic necrosis. VI. Metabolic disposition of toxic and nontoxic doses of acetaminophen. Pharmacology (Basel), 12, 251–271.
  • LAEMMILI, U. K., 1970, Cleavage of structural proteins during assembly of the head bacteriophage T4. Nature, 227, 680–685.
  • LlESHOUT, E. M. M., PETERS, W. H. M. and JANSEN, J. B. M. J., 1996, Effect of oltipraz, a-tocopherol, /3-carotene and phenethylisothiocyanate on rat oesophageal, gastric, colonic and hepatic gluta-thione, glutathione S-transferase and peroxidase. Carcinogenesis, 17, 1439–1445.
  • LOWRY, O. H., ROSEBROUGH, N. J., FARR, A. L. and RANDALL, R. T., 1951, Protein measurement with the Folin phenol reagent. Journal of Biological Chemistry, 193, 265–275.
  • MANNERV1K, B. and DANIELSON, U. H., 1988, Glutathione transferases; structure and catalytic activity. Critical Reviews in Biochemistry and Molecular Biology, 23, 281–337.
  • MITCHELL, J. R. and JoHow,, D. J., 1975, Metabolic activation of drugs to toxic substances. Gastroenterology, 68, 392.
  • MITCHELL, J. R., JoHow, D. J., POTIER, W. Z., DAVIS, D. C., G1LETTE, J. R. and BRODIE, B. B., 1973b, Acetaminophen-induced hepatic necrosis. I. Role of drug metabolism. Journal of Pharmacology and Experimental Therapeutics, 187, 185–194.
  • MITCHELL, J. R., JoHow, D. J., POTTER, W. Z., DAVIS, D. C., GILETIE, J. R. and BRODIE, B. B., 1973a, Acetaminophen-induced hepatic necrosis. IV. Protective role of glutathione. Journal of Phar-macology and Experimental Therapeutics, 187, 211–217.
  • MORSE, M. A., AWN, S. G., HECHT, S. S. and CHUNG, F.-L., 1989b, Effects of aromatic isothiocyanates on tumorigenicity, O6-methylguanine formation, and metabolism of the tobacco-specific nitrosamine 4-(methylnitrosamino)-1-(3-pyidy1)-1-butanone in A /J mouse lung. Cancer Research, 49, 2894–2897.
  • MORSE, MA., WANG, C.-X., STONER, G. D., MANDAL, S., Co, P. B., AMIN, S. G., HECHT, S. S. and CHUNG, F.-L., 1989a, Inhibition of 4-(methylnitrosamino) -1 -(3-pyridy1)-1 -butanone-induce d DNA adduct formation and tumorigenicity in the lung of F344 rats by dietary phenethyl isothiocyanate. Cancer Research, 49,549–553.
  • POTTER, W. Z., THORGE1RSSON, S. S., JoHow, D. J. and MITCHELL, J. R., 1974, Acetaminophen-induced hepatic necrosis, V. Correlation of hepatic necrosis, covalent binding and glutathione depletion in hamsters. Pharmacology (Basel), 12, 129–143.
  • PUISSANT, C. and HOUDEBINE, L. M., 1990, An improvement of the single-step method of RNA isolation by acid guanidinium thiocyanate—phenol—chloroform extraction. Bio techniques, 8,148–149.
  • REYES, H., LEVI, A. J., GATMAITAN, Z. and ARIAS, I. M., 1971, Studies of Y and Z, two hepatic cytoplasmic organic anion-binding proteins; Effect of drugs, chemicals, hormones, and choles-tasis. Journal of Clinical Investigation, 50, 2242–2252.
  • SlEGERS, C.-P., STRUBLET, O. and SCHUTT, A, 1978, Relations between hepatotoxicity and pharmaco-kinetics of paracetamol in rats and mice. Pharmacology (Basel), 16, 273–278.
  • SMITH, R. L., 1973, The excretory function of bile. In The Elimination of Drugs and Toxic Substances in Bile (London: Chapman & Hall).
  • 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-pyridy1)-1 -butanone bioactivation in mouse by dietary phenethyl isothiocyanate. Cancer Research, 53, 3276–3282.
  • STEINMETZ, K. A. and POTTER, J. D., 1991, Vegetables, fruit and cancer. I. Epidemiology. Cancer Causes and Control, 2, 325–357.
  • STRANGE, R. C., MATHAROO, B., FAULDER, G. C., Jos, P., COTTON, W., ELDER, J. B. and DEAKIN-, M., 1991, The human glutathione S-transferases; a case control study of the incidence of the GST1 phenotype in patients with adenocarcinoma. Carcinogenesis, 2, 25–28.
  • TlETZE, F., 1969, Enzymatic method for quantitative determination of nanogram amounts of total and oxidized glutathione; Application to mammalian blood and other tissues. Analytical Biochemistry, 27, 502–522.
  • TOOKEY, H. L., VANETTEN, C. H. and DAXENBICHLER, M. E., 1980, Glucosinolates. In I. E. Liener (ed.), Toxic Constituents of Plant Foodstuffi (New York: Academic Press), pp. 103–142.
  • TROCK, B., LANZA, E. and GREENWALD, P., 1990, Dietary fiber, vegetables and colon cancer; a critical review and meta-analysis of the epidemiologic evidence. Journal of the National Cancer Institute, 82, 650–661.
  • WALLIN, J. D., CLIFTON, G. and KAPLown7, N., 1978, The effect of phenobarbital, probenecid and diethyl maleate on the pharmacokinetics and biliary excretion of ethacrynic acid in the rat. journal of Pharmacology and Experimental Therapeutics, 205, 471–479.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.