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Xenobiotica
the fate of foreign compounds in biological systems
Volume 34, 2004 - Issue 7
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Research Article

Phytochemical-induced changes in gene expression of carcinogen-metabolizing enzymes in cultured human primary hepatocytes

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Pages 619-632 | Received 24 Mar 2004, Published online: 22 Sep 2008

Reference

  • BACON, J. R., WILLIAMSON, G., GARNER, R. C., LAPPIN, G., LANGOUET, S. and BAO, Y., 2003, Sulforaphane and quercetin modulate PhIP—DNA adduct formation in human HepG2 cells and hepatocytes. Carcinogenesis, 24, 1903–1911.
  • BARCELO, S., MACE, K., PFEIFER A. M. and CHIPMAN, J. K., 1998, Production of DNA strand breaks by N-nitrosodimethylamine and 2-amino-3-methylimidazo[4,5-flquinoline in THLE cells expressing human CYP isoenzymes and inhibition by sulforaphane. Mutation Research, 402, 111–1120.
  • BEGLEITER, A. and LANGE, L., 2002, Lack of NQ01 induction in human tumor cells is not due to changes in the promoter region of the gene. International Journal of Oncology, 20, 835–838.
  • BJELDANES, L. F., KIM, J. Y., GROSE, K. R., BARTHOLOMEW, J. C. and BRADFIELD, C. A., 1991, Aromatic hydrocarbon responsiveness-receptor agonists generated from indole-3-carbinol in vitro and in vivo: comparisons with 2,3,7,8-tetrachlorodibenzo-p-dioxin. Proceedings of the National Academy of Sciences, USA, 88, 9543–9547.
  • BONNESEN, C., EGGLESTON, I. M. and HAYES, J. D., 2001, Dietary indoles and isothiocyanates that are generated from cruciferous vegetables can both stimulate apoptosis and confer protection against DNA damage in human colon cell lines. Cancer Research, 61, 6120–6130.
  • CANISTRO, D., DELLA CROCE, C., BARILLARI, J., BRONZETTI, G., Pm, G., CINI, M., CALTUVUTRO, L., PEROCCO, P. and PAOLINI, M. 2004, Genetic and metabolic effects of gluconasturtiin, a glucosinolate derived from cruciferae. Mutation Research, 545, 23–35.
  • CHEN, C. M. and FANG, H. C., 1997, Chemical analysis of the active principles of Curcuma species. In C. Y. Sung (ed.), Modern Treatise in Chinese Herbal Medicines (Beijing: Institute of Pharmaceutical Sciences, Medical Academia), Vol. III, pp. 95–105.
  • CHEN, I., McDouGAL A., WANG, F. and SAFE, S., 1998, Aryl hydrocarbon receptor-mediated antiestrogenic and antitumorigenic activity of diindolylmethane. Carcinogenesis, 19, 1631–1639.
  • CHEN, I., SAFE, S. and BJELDANES, L., 1996, Indole-3-carbinol and diindolylmethane as aryl hydrocarbon (Ah) receptor agonists and antagonists in T47D human breast cancer cells. Biochemical Pharmacology, 51, 1069–1076.
  • 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 Epidemiology Biomarkers and Prevention, 1, 383–388.
  • CIOLINO, H. P., DASCHNER, P. J., WANG, T. T. and YEH, G. C., 1998, Effect of curcumin on the aryl hydrocarbon receptor and cytochrome P450 1A1 in MCF-7 human breast carcinoma cells. Biochemical Pharmacology, 56, 197–206.
  • CISKA, E., MARTYNIAK-PRZYBYSZEWSKA, B. and KOZLOWSKA, H., 2000, Content of glucosinolates in cruciferous vegetables grown at the same site for two years under different climatic conditions. Journal of Agricultural and Food Chemistry, 48, 2862–2867.
  • DE KRUIF, C. A,, MARSMAN, J. W., VENEKAMP, J. C., FALKE, H. E., NOORDHOEK, J., BLAAUBOER, B. J. and WORTELBOER, H. M., 1991, Structure elucidation of acid reaction products of indole-3-carbinol: detection in vivo and enzyme induction in vitro. Chemico-Biological Interactions, 80, 303–315.
  • DINKOVA-KOSTOV A. T. and TALALAY, P., 1999, Relation of structure of curcumin analogs to their potencies as inducers of Phase 2 detoxification enzymes. Carcinogenesis, 20, 911–914.
  • DINKOVA-KOSTOV A. T. and TALALAY, P., 2000, Persuasive evidence that quinone reductase type 1 (DT diaphorase) protects cells against the toxicity of electrophiles and reactive forms of oxygen. Free Radical Biology and Medicine, 29, 231–240.
  • DUKE, J. A., 1992, Handbook of Phytochemical Constituents of GRAS Herbs and Other Economic Plants (Boca Raton: CRC Press).
  • EATON, D. L. and BAMMLER, T. K., 1999, Concise review of the glutathione S-transferases and their significance to toxicology. Toxicological Sciences, 49, 156–164.
  • ERICKSON, A. M., NEVAREA, Z., GIPP, J. J. and MULCAHY, R. T., 2002, Identification of a variant antioxidant response element in the promoter of the human glutamate-cysteine ligase modifier subunit gene. Revision of the ARE consensus sequence. Journal of Biological Chemistry, 277, 30730–30737.
  • GERHAUSER, C., You, M., Liu, J., MORIARTY, R.M., HAWTHORNE, M., MEHTA, R. G., MOON, R. C. and PEZZUTO, J. M., 1997, Cancer chemopreventive potential of sulforamate, a novel analogue of sulforaphane that induces phase 2 drug-metabolizing enzymes. Cancer Research, 57, 272.
  • GIBSON, G. G., PLANT, N. J., SWALES, K. E., AYRTON, A. and EL-SANKARY, W., 2002, Receptor-dependent transcriptional activation of cytochrome P4503A genes: induction mechanisms, species differences and interindividual variation in man. Xenobiotica, 32, 165–206.
  • GROSS-STEINMEYER, K., STAPLETON, P. L., TRACY, J. H., BAMMLER, T. K., STROM, S. C. and EATON, D. L., 2002, Influence of matrigel-overlay on constitutive and inducible expression of nine genes encoding drug metabolizing enzymes in primary human hepatocytes. Toxicologist, 66, 229.
  • HAMILTON, S. M. and TEEL, R. W., 1996, Effects of isothiocyanates on cytochrome P-450 1A1 and 1A2 activity and on the mutagenicity of heterocyclic amines. Anticancer Research, 16, 3597–3602.
  • HAYES, J. D., PULFORD, D. J., ELLIS, E. M., McLE0D, R., JAMES, R. F., SEIDEGARD, J., MOSIALOU, E., JERNSTROM, B. and NEAL, G. E., 1998, Regulation of rat glutathione S-transferase A5 by cancer chemopreventive agents: mechanisms of inducible resistance to aflatoxin Bl. Chemico-Biological Interactions, 111–112, 51–67.
  • HECHT, S. S., 1995, Chemoprevention by isothiocyanates. Journal of Cellular Biochemistry, 22 (Suppl.), 195–209.
  • HECHT, S. S., CHUNG, F. L., RICHIE, J. P. JR, AKERKAR, S. A., BORUKHOVA, A., SKOWRONSKI, L. and CARMELLA, S. G., 1995, Effects of watercress consumption on metabolism of a tobacco-specific lung carcinogen in smokers. Cancer Epidemiology Biomarkers and Prevention, 4, 877–884.
  • HENDERSON, M. C., MIRANDA, C. L., STEVENS, J. F., DEINZER, M. L. and BUHLER, D. R., 2000, In vitro inhibition of human P450 enzymes by prenylated flavonoids from hops, Humulus lupulus. Xenobiotica, 30, 235–251.
  • JiAo, D., CONAWAY, C. C., WANG, M. H., YANG, C. S., KOEHL, W. and CHUNG, F. L., 1996, 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, 9, 932–938.
  • KALL, M. A., VANG, 0. and CLAUSEN, J., 1996, Effects of dietary broccoli on human in vivo drug metabolizing enzymes: evaluation of caffeine, oestrone and chlorzoxazone metabolism. Carcinogenesis, 17, 793–799.
  • KELLOFF, G. J., CROWELL, J. A., STEELE, V. E., LUBET, R. A., MALONE, W. A., BOONE, C. W., KOPELOVICH, L., HAWK, E. T., LIEBERMAN, R., LAWRENCE, J. A., ALI, I., VINER, J. L. and SIGMAN, C. C., 2000, Progress in cancer chemoprevention: development of diet-derived chemopreventive agents. Journal of Nutrition, 130 (Suppl.), 467S–471S.
  • KROVAT, B. C, TRACY, J. H. and OMIECINSKI, C. J., 2000, Fingerprinting of cytochrome P450 and microsomal epoxide hydrolase gene expression in human blood cells. Toxicological Sciences, 55, 352–360.
  • KUSHAD, M. M., BROWN, A. F., KURILICH, A. C., JuviK, J. A., KLEIN, B. P., WALLIG, M. A. and JEFFERY, E. H., 1999, Variation of glucosinolates in vegetable crops of Brassica oleracea. Journal of Agricultural and Food Chemistry, 47, 1541–1548.
  • LAKE, B. G., TREDGER, J. M., RENWICK, A. B., BARTON, P. T. and PRICE, R. J., 1998, 3,3'-Diindolylmethane induces CYP1A2 in cultured precision-cut human liver slices. Xenobiotica, 28, 803–811.
  • LAMPE, J. W., KING, I. B., LI, S., GRATE, M. T., BARALE, K. V., CHEN, C., FENG, Z. and POTTER, J. D., 2000, Brassica vegetables increase and apiaceous vegetables decrease cytochrome P450 1A2 activity in humans: changes in caffeine metabolite ratios in response to controlled vegetable diets. Carcinogenesis, 21, 1157–1162.
  • LEE, S. K., SONG, L., MATA-GREENWOOD, E., KELLOFF, G. J., STEELE, V. E. and PEZZUTO, J. M., 1999, Modulation of in vitro biomarkers of the carcinogenic process by chemopreventive agents. Anticancer Research, 19, 35–44.
  • LEIBELT, D. A., HEDSTROM, 0. R., FISCHER, K. A., PEREIRA, C. B. and WILLIAMS, D. E., 2003, Evaluation of chronic dietary exposure to indole-3-carbinol and absorption-enhanced 3,3'-diindolylmethane in Sprague—Dawley rats. Toxicological Sciences, 74, 10–21.
  • LIEBES,. L, CONAWAY, C. C., HOCHSTER, H, MENDOZA, S., HECHT, S. S., CROWELL, J. and CHUNG. F. L., 2001, High-performance liquid chromatography-based determination of total isothiocyanate levels in human plasma: application to studies with 2-phenethyl isothiocyanate. Analytical Biochemistry, 291, 279–289.
  • LIN, J. K. and LIN-SHIA, S. Y., 2001, Mechanisms of cancer chemoprevention by curcumin. Proceedings of the National Science Council (Republic of China), 25, 59–66.
  • MAHEO, K., MOREL, F., LANGOUET, S., KRAMER, H., LE FERREC, E., KETTERER, B. and GUILLOUZO, A., 1997, Inhibition of cytochromes P-450 and induction of glutathione S-transferases by sulforaphane in primary human and rat hepatocytes. Cancer Research, 57, 3649–3652.
  • MANSON, M. M., BALL, H. W., BARRETT, M. C., CLARK, H. L., JUDAH, D. J., WILLIAMSON, G. and NEAL, G. E., 1997, Mechanism of action of dietary chemoprotective agents in rat liver: induction of phase I and II drug metabolizing enzymes and afiatoxin B1 metabolism. Carcinogenesis, 18, 1729–1738.
  • MANSON, M. M., GESCHER, A., HUDSON, E. A., PLUMMER, S. M., SQUIRES, M. S. and PRIGENT, S. A., 2000, Blocking and suppressing mechanisms of chemoprevention by dietary constituents. Toxicological Letters, 112–113, 499–505.
  • MCCARTY, M. F., 2001, Inhibition of CYP2E1 with natural agents may be a feasible strategy for minimizing the hepatotoxicity of ethanol. Medical Hypotheses, 56, 8–11.
  • MCDANELL, R. E., HENDERSON, L. A., RUSSELL, K. and MCLEAN, A. E., 1992, The effect of Brassica vegetable consumption on caffeine metabolism in humans. Human and Experimental Toxicology, 11, 167–172.
  • MIRANDA, C. L., APONSO, G. L., STEVENS, J. F., DEINZER, M. L. and BUHLER, D. R., 2000b, Prenylated chalcones and fiavanones as inducers of quinone reductase in mouse Hepa 1c1c7 cells. Cancer Letters, 149, 21–29.
  • MIRANDA, C. L., YANG, Y. H., HENDERSON, M. C., STEVENS, J. F., SANTANA-RIOS, G., DEINZER, M. L. and BUHLER, D. R., 2000a, Prenylfiavonoids from hops inhibit the metabolic activation of the carcinogenic heterocyclic amine 2-amino-3-methylimidazo[4,5-f]quinoline, mediated by cDNA-expressed human CYP1A2. Drug Metabolism and Disposition, 28, 1297–1302.
  • MURRAY, G. I., MELVIN, W. T., GREENLEE, W. F. and BURKE, M. D., 2001, Regulation, function, and tissue-specific expression of cytochrome P450 CYP1B1. Annual Reviews of Pharmacology and Toxicology, 41, 297–316.
  • NAKAJIMA, M., YOSHIDA, R., SHIMADA, N., YAMAZAKI, H. and YOKOI, T., 2001, Inhibition and inactivation of human cytochrome P450 isoforms by phenethyl isothiocyanate. Drug Metabolism and Disposition, 29, 1110–1113.
  • PANTUCK, E. J., PANTUCK, C. B., GARLAND, W. A., MIN, B. H., WATTENBERG, L. W., ANDERSON, K. E., KAPPAS, A. and CONNEY, A. H., 1979, Stimulatory effect of Brussels sprouts and cabbage on human drug metabolism. Clinical Pharmacology and Therapeutics, 25, 88–95.
  • PULFORD, D. J. and HAYES, J. D., 1996, Characterization of the rat glutathione S-transferase Yc2 subunit gene, GSTA5: identification of a putative antioxidant-responsive element in the 5'-flanking region of rat GSTA5 that may mediate chemoprotection against aflatoxin Bl. Biochemical Journal, 318, 75–84.
  • RENWICK, A. B., MISTRY, H., BARTON, P. T., MALLET, F., PRICE, R. J., BEAMAND, J. A. and LAKE, B. G., 1999, Effect of some indole derivatives on xenobiotic metabolism and xenobiotic-induced toxicity in cultured rat liver slices. Food and Chemical Toxicology, 37, 609–618.
  • SANDERSON, J. T., SLOBBE, L., LANSBERGEN, G. W., SAFE, S. and VAN DEN BERG, M., 2001, 2,3,7,8-Tetrachlorodibenzo-p-dioxin and diindolylmethanes differentially induce cytochrome P450 1A1, 1B1, and 19 in H295R human adrenocortical carcinoma cells. Toxicological Sciences, 61, 40–48.
  • SHARMA, R. A., IRESON, C. R., VERSCHOYLE, R. D., HILL, K. A., WILLIAMS, M. L., LEURATTI, C., MANSON, M. M., MARNETT, L. J., STEWARD, W. P. and GESCHER, A., 2001, Effects of dietary curcumin on glutathione S-transferase and malondialdehyde-DNA adducts in rat liver and colon mucosa: relationship with drug levels. Clinical Cancer Research, 7, 1452–1458.
  • SHERTZER, H. G. and SENFT, A. P., 2001, The micronutrient indole-3-carbinol: implications for disease and chemoprevention. Drug Metabolism and Drug Interaction, 17, 159–188.
  • SIDHU, J. S., FARIN, F. M. and OMIECINSKI, C. J., 1993, Influence of extracellular matrix overlay on phenobarbital-mediated induction of CYP2B1, 2B2, and 3A1 genes in primary adult rat hepatocyte culture. Archives of Biochemistry and Biophysics, 301, 103–113.
  • SINGLETARY, K. and MACDONALD, C., 2000, Inhibition of benzo[a]pyrene- and 1,6-dinitropyrene-DNA adduct formation in human mammary epithelial cells bydibenzoylmethane and sulforaphane. Cancer Letters, 155, 47–54.
  • SMITH, T. J., Guo, Z., GUENGERICH, F. P. and YANG, C. S., 1996, Metabolism of 4-(methyl-nitrosamino)-1-(3-pyridy1)-1-butanone (NNK) by human cytochrome P450 1A2 and its inhibition by phenethyl isothiocyanate. Carcinogenesis, 17, 809–813.
  • STEVENS, J. F., TAYLOR, A. W., CLAWSON, J. E. and DEINZER, M. L., 1999b, Fate of xanthohumol and related prenylflavonoids from hops to beer. Journal Agricultural and Food Chemistry, 47, 2421–2428.
  • STEVENS, J. F., TAYLOR, A. W. and DEINZER, M. L., 1999a, Quantitative analysis of xanthohumol and related prenylflavonoids in hops and beer by liquid chromatography-tandem mass spectrometry. Journal of Chromatography A, 832, 97–107.
  • STRESSER, D. M., WILLIAMS, D. E., GRIFFIN, D. A. and BAILEY, G. S., 1995, Mechanisms of tumor modulation by indole-3-carbinol. Disposition and excretion in male Fischer 344 rats. Drug Metabolism and Disposition, 23, 965–975.
  • STROM, S. C., PISAROV, L. A., DORKO, K., THOMPSON, M. L., SCHUETZ, J. D. and SCHUETZ, E. G., 1996, Use of human hepatocytes to study P450 gene induction. Methods in Enzymology, 272, 388–401. TALALAY, P., FAHEY, J. W., HOLTZCLAW, W. D., PRESTERA, T. and ZHANG, Y., 1995, Chemoprotection against cancer by phase 2 enzyme induction. Toxicological Letters, 82–83, 173–179.
  • VAN TEASEL, M. L., PLOEMEN, J. P., Lo BELLO, M., FEDERICI, G. and VAN BLADEREN, P. J., 1997, Interactions of alpha, beta-unsaturated aldehydes and ketones with human glutathione 5-transferase P1-1. Chemico-Biological Interactions, 108, 67–78.
  • VAN LIESHOUT, E. M., PETERS, W. H. and JANSEN, J. B., 1996, Effect of oltipraz, alpha-tocopherol, beta-carotene and phenethylisothiocyanate on rat oesophageal, gastric, colonic and hepatic glutathione, glutathione S-transferase and peroxidase. Carcinogenesis, 17, 1439–1445.
  • WALLIG, M. A., KINGSTON, S., STAACK, R. and JEFFEREY, E. H., 1998, Induction of rat pancreatic glutathione S-transferase and quinone reductase activities by a mixture of glucosinolate breakdown derivatives found in Brussels sprouts. Food and Chemical Toxicology, 36, 365–373.
  • WANG, X., DOHERTY, G. P., LEITH, M. K., CURPHEY, T. J. and BEGLEITER, A., 1999, Enhanced cytotoxicity of mitomycin C in human tumour cells with inducers of DT-diaphorase. British Journal of Cancer, 80, 1223–1230.
  • WILKINSON IV, J. and CLAPPER, M. L., 1997, Detoxication enzymes and chemoprevention. Proceedings of the Society of Experimental Biology and Medicine, 216, 192–200.
  • WOERTELBOER, H. M., DEKRUIF, C. A., VAN TEASEL, A. A., FALKE, H. E., NOORDHOEK, J. and BLAAUBOER, B. J., 1992, Acid reaction products of indole-3-carbinol and their effects on cytochrome P450 and phase II enzymes in rat and monkey hepatocytes. Biochemical Pharmacology, 43, 1439–1447.
  • Xu, K. and THORNALLEY, P. J., 2000, Studies on the mechanism of the inhibition of human leukemia cell growth by dietary isothiocyanates and their cysteine adducts in vitro. Biochemical Pharmacology, 60, 221–231.
  • Xu, L., LI, A. P., KAA/INsEI, D. L. and Rux, M. F., 2000, 2,3,7,8-Tetrachlorodibenzo-p-dioxin induction of cytochrome P4501A in cultured rat and human hepatocytes. Chemico-Biological Interactions, 124, 173–189.
  • ZHANG, Y., KENSLER, T. W., CHO, C. G., POSNER, G. H. and TALALAY, P., 1994, Anticarcinogenic activities of sulforaphane and structurally related synthetic norbornyl isothiocyanates. Proceedings of the National Academy of Sciences of the United States of America, 91, 3147–3150.

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