Advertisement

Modifiers of Cytochrome(s) P450

  • John DiGiovanni
  • Heather E. Kleiner
Chapter
Part of the Cancer Drug Discovery and Development book series (CDD&D)

Abstract

Cytochromes P450 (CYPs) belong to a superfamily of enzymes that have different, but overlapping, substrate specificities and tissue distribution. The highest concentration of CYPs is in the liver endoplasmic reticulum, but P450 is found in most other tissues of the body. CYPs are heme-containing enzymes that can either detoxify or bioactivate xenobiotics (foreign chemicals). The following seven types of reactions are catalyzed by CYPs: i) hydroxylation of an aliphatic or aromatic carbon; ii) epoxidation of a double bond; iii) heteroatom (S-, N-, and I-) oxygenation and N-hydroxylation; iv) heteroatom (O-, S-, and N-) dealkylation; v) oxidative group transfer; vi) cleavage of esters; and vii) dehydrogenation (1). In humans, the predominant isoform of P450 in the liver is CYP1A2. Other human liver P450s include CYP 2A6, 2B6, 2C8, 2C9, 2C19, 2D6, 2E1, and 3A4 (reviewed in ref. 1). CYP 1 A 1 is expressed in extrahepatic sites including human lung, the intestines, the skin, lymphocytes, and the placenta. Human CYP 1 B 1 catalyzes the activation of a number of diverse pro-carcinogens (2), and is expressed in a variety of extra-hepatic sites, including steroid-responsive and steroidogenic tissues (3–5).

Keywords

Ursolic Acid Organosulfur Compound Rosemary Extract Mouse Epidermis Diallyl Disulfide 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Parkinson A. Biotransformation of xenobiotics, in Casarett and Doull’s Toxicology: The Basic Science of Poisons, 5th ed. Klaasen C, ed. McGraw-Hill, New York, 1996, pp.113–186.Google Scholar
  2. 2.
    Shimada T, Hayes CL, Yamazaki H, et al. Activation of chemically diverse procarcinogens by human cytochrome P-450 1B1. Cancer Res 1996;56:2979–2984.PubMedGoogle Scholar
  3. 3.
    Alexander DL, Eltom SE, Jefcoate CR. Ah receptor regulation of CYP 1 B 1 expression in primary mouse embryo-derived cells. Cancer Res 1997;57:4498–4506.PubMedGoogle Scholar
  4. 4.
    Brake PB, Jefcoate CR. Regulation of cytochrome P4501 B 1 in cultured rat adrenocortical cells by cyclic adenosine 3’,5’-monophosphate and 2,3,7,8-tetrachlorodibenzo-p-dioxin. Endocrinology 1995;136:5034–5041.PubMedCrossRefGoogle Scholar
  5. 5.
    Savas U, Bhattacharyya KK, Christou M, et al. Mouse cytochrome P-450EF, representative of a new 1B subfamily of cytochrome P-450s. Cloning, sequence determination, and tissue expression. J Biol Chem 1994;269:14,905–14,911.Google Scholar
  6. 6.
    McLemore TL, Adelberg S, Liu MC, et al. Expression of CYP 1 A 1 gene in patients with lung cancer: evidence for cigarette smoke-induced gene expression in normal lung tissue and for altered gene regulation in primary pulmonary carcinomas. J Natl Cancer Inst 1990;82:1333–1339.PubMedCrossRefGoogle Scholar
  7. 7.
    Song BJ, Gelboin HV, Park SS, et al. Monoclonal antibodydirected radioimmunoassay detects cytochrome P-450 in human placenta and lymphocytes. Science 1985;228:490–492.PubMedCrossRefGoogle Scholar
  8. 8.
    Hasler JA, Estabrook R, Murray M, et al. Human cytochromes P450. Mol Aspects Med 1999;20:1–137.CrossRefGoogle Scholar
  9. 9.
    Kensler TW, Egner PA, Trush MA, et al. Modification of aflatoxin B1 binding to DNA in vivo in rats fed phenolic antioxidants, ethoxyquin and a dithiothione. Carcinogenesis 1985;6:759–763.PubMedCrossRefGoogle Scholar
  10. 10.
    Kensler TW, Egner PA, Dolan PM, et al. Mechanism of protection against aflatoxin tumorigenicity in rats fed 5-(2-pyrazinyl)-4-methyl-1,2-dithiol-3-thione (oltipraz) and related 1,2-dithiol-3-thiones and 1,2-dithiol-3-ones. Cancer Res 1987;47:4271–4277.PubMedGoogle Scholar
  11. 11.
    Kensler TW, Groopman JD, Eaton DL, et al. Potent inhibition of aflatoxin-induced hepatic tumorigenesis by the monofunctional enzyme inducer 1,2-dithiole-3-thione. Carcinogenesis 1992;13:95–100.PubMedCrossRefGoogle Scholar
  12. 12.
    Rao CV, Rivenson A, Zang E, et al. Inhibition of 2-amino1-methyl-6-phenylimidazo[4,5]pyridine-induced lymphoma formation by oltipraz. Cancer Res 1996;56:3395–3398.PubMedGoogle Scholar
  13. 13.
    Meyer DJ, Harris JM, Gilmore KS, et al. Quantitation of tissue- and sex-specific induction of rat GSH transferase subunits by dietary 1,2-dithiole-3-thiones. Carcinogenesis 1993;14:567–572.PubMedCrossRefGoogle Scholar
  14. 14.
    Raney KD, Meyer DJ, Ketterer B, et al. Glutathione conjugation of aflatoxin B1 exo- and endo-epoxides by rat and human glutathione S-transferases. Chem Res Toxicol 1992;5:470–478.PubMedCrossRefGoogle Scholar
  15. 15.
    Langouet S, Maheo K, Berthou F, et al. Effects of administration of the chemoprotective agent oltipraz on CYP 1 A and CYP2B in rat liver and rat hepatocytes in culture. Carcinogenesis 1997;18:1343–1349.PubMedCrossRefGoogle Scholar
  16. 16.
    Guengerich FP, Johnson WW, Shimada T, et al. Activation and detoxication of aflatoxin B 1. Mutat Res 1998;402:121–128.PubMedCrossRefGoogle Scholar
  17. 17.
    Kensler TW, Curphey TJ, Maxiutenko Y, Roebuck BD. Chemoprotection by organosulfur inducers of phase 2 enzymes: dithiolethiones and dithiins. Drug Metabol Drug Interact 2000;17:3–22.PubMedCrossRefGoogle Scholar
  18. 18.
    Le Bon AM, Siess MH. Organosulfur compounds from Allium and the chemoprevention of cancer. Drug Metabol Drug Interact 2000;17:51–79.PubMedCrossRefGoogle Scholar
  19. 19.
    Wargovich MJ, Woods C, Eng VW, et al. Chemoprevention of N-nitrosomethylbenzylamine-induced esophageal cancer in rats by the naturally occurring thioether, diallyl sulfide. Cancer Res 1988;48:6872–6875.PubMedGoogle Scholar
  20. 20.
    Sparnins VL, Barany G, Wattenberg LW. Effects of organosulfur compounds from garlic and onions on benzo[a]pyrene-induced neoplasia and glutathione S-transferase activity in the mouse. Carcinogenesis 1988;9:131–134.PubMedCrossRefGoogle Scholar
  21. 21.
    Suzui N, Sugie S, Rahman KM, et al. Inhibitory effects of diallyl disulfide or aspirin on 2-amino- l -methyl-6-phenylimidazo[4,5-b]pyridine-induced mammary carcinogenesis in rats. Jpn J Cancer Res 1997;88:705–711.PubMedCrossRefGoogle Scholar
  22. 22.
    Guyonnet D, Belloir C, Suschetet M, et al. Antimutagenic activity of organosulfur compounds from Allium is associated with phase 2 enzyme induction. Mutat Res 2001;495:135–145.PubMedCrossRefGoogle Scholar
  23. 23.
    Srivastava SK, Hu X, Xia H, et al. Mechanism of differential efficacy of garlic organosulfides in preventing benzo(a)pyrene-induced cancer in mice. Cancer Lett 1997;118:61–67.PubMedCrossRefGoogle Scholar
  24. 24.
    Teyssier C, Amiot MJ, Mondy N, et al. Effect of onion consumption by rats on hepatic drug-metabolizing enzymes. Food Chem Toxicol 2001;39:981–987.PubMedCrossRefGoogle Scholar
  25. 25.
    Brady JF, Ishizaki H, Fukuto JM, et al. Inhibition of cytochrome P-450 2E1 by diallyl sulfide and its metabolites. Chem Res Toxicol 1991;4:642–647.PubMedCrossRefGoogle Scholar
  26. 26.
    Yamazaki H, Inui Y, Yun CH, et al. Cytochrome P450 2E1 and 2A6 enzymes as major catalysts for metabolic activation of N-nitrosodialkylamines and tobacco-related nitrosamines in human liver microsomes. Carcinogenesis 1992;13:1789–1794.PubMedCrossRefGoogle Scholar
  27. 27.
    Patten CJ, Smith TJ, Friesen MJ, et al. Evidence for cytochrome P450 2A6 and 3A4 as major catalysts for N’-nitrosonornicotine alpha-hydroxylation by human liver microsomes. Carcinogenesis 1997;18:1623–1630.PubMedCrossRefGoogle Scholar
  28. 28.
    Kushida, H., Fujita, K., Suzuki, A., et al. Development of a Salmonella tester strain sensitive to promutagenic N-nitrosamines: expression of recombinant CYP2A6 and human NADPH-cytochrome P450 reductase in S. typhimurium YG7108. Mutat Res 2000;471:135–143.PubMedCrossRefGoogle Scholar
  29. 29.
    Kushida, H., Fujita, K., Suzuki, A., et al. Metabolic activation of N-alkylnitrosamines in genetically engineered Salmonella typhimurium expressing CYP2E1 or CYP2A6 together with human NADPH-cytochrome P450 reductase. Carcinogenesis 2000;21:1227–1232.PubMedCrossRefGoogle Scholar
  30. 30.
    Genter MB, Liang HC, Gu J, et al. Role of CYP2A5 and 2G1 in acetaminophen metabolism and toxicity in the olfactory mucosa of the Cyp l a2(-/-) mouse. Biochem Pharmacol 1998;55:1819–1826.PubMedCrossRefGoogle Scholar
  31. 31.
    Wattenberg LW, Sparnins VL, Barany G. Inhibition of N-nitrosodiethylamine carcinogenesis in mice by naturally occurring organosulfur compounds and monoterpenes. Cancer Res 1989;49:2689–2692.PubMedGoogle Scholar
  32. 32.
    Takahashi S, Hakoi K, Yada H, et al. Enhancing effects of diallyl sulfide on hepatocarcinogenesis and inhibitory actions of the related diallyl disulfide on colon and renal carcinogenesis in rats. Carcinogenesis1992;13:1513–1518.CrossRefGoogle Scholar
  33. 33.
    Fujita K, Kamataki T. Screening of organosulfur compounds as inhibitors of human CYP2A6. Drug Metab Dispos 2001;29:983–989.PubMedGoogle Scholar
  34. 34.
    Testa B, Jenner P. Inhibitors of cytochrome P-450s and their mechanism of action. Drug Metab Rev 1981;12:1–117.PubMedCrossRefGoogle Scholar
  35. 35.
    Hong JY, Wang ZY, Smith TJ, et al. Inhibitory effects of diallyl sulfide on the metabolism and tumorigenicity of the tobacco-specific carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) in A/J mouse lung. Carcinogenesis 1992;13:901–904.PubMedCrossRefGoogle Scholar
  36. 36.
    Huang MT, Wang ZY, Georgiadis CA, et al. Inhibitory effects of curcumin on tumor initiation by benzo[a]pyrene and 7,12-dimethylbenz[a]anthracene. Carcinogenesis 1992;13:2183–2186.PubMedCrossRefGoogle Scholar
  37. 37.
    Chuang SE, Kuo ML, Hsu CH, et al. Curcumin-containing diet inhibits diethylnitrosamine-induced murine hepatocarcinogenesis. Carcinogenesis 2000;21:331–335.PubMedCrossRefGoogle Scholar
  38. 38.
    Huang MT, Lou YR, Ma W. et al. Inhibitory effects of dietary curcumin on forestomach, duodenal, and colon carcinogenesis in mice. Cancer Res 1994;54:5841–5847.PubMedGoogle Scholar
  39. 39.
    Sohn OS, Ishizaki H, Yang CS, Fiala ES. Metabolism of azoxymethane, methylazoxymethanol and N-nitrosodimethylamine by cytochrome P450IIE 1. Carcinogenesis 1991;12:127–131.PubMedCrossRefGoogle Scholar
  40. 40.
    Lin CC, Lu YP, Lou YR, et al. Inhibition by dietary dibenzoylmethane of mammary gland proliferation, formation of DMBA-DNA adducts in mammary glands, and mammary tumorigenesis in Sencar mice. Cancer Lett 2001;168:125–132.PubMedCrossRefGoogle Scholar
  41. 41.
    Huang MT, Lou YR, Xie JG, et al. Effect of dietary curcumin and dibenzoylmethane on formation of 7,12-dimethylbenz[a]anthracene-induced mammary tumors and lymphomas/leukemias in Sencar mice. Carcinogenesis 1998;19:1697–1700.PubMedCrossRefGoogle Scholar
  42. 42.
    Kawamori T, Lubet R, Steele VE, et al. Chemopreventive effect of curcumin, a naturally occurring anti-inflammatory agent, during the promotion/progression stages of colon cancer. Cancer Res 1999;59: 597–601.PubMedGoogle Scholar
  43. 43.
    Thapliyal R, Maru GB. Inhibition of cytochrome P450 isozymes by curcumins in vitro and in vivo. Food Chem Toxicol 2001;39:541–547.PubMedCrossRefGoogle Scholar
  44. 44.
    Allen SW, Mueller L, Williams SN, et al. The use of a high-volume screening procedure to assess the effects of dietary flavonoids on human cyp 1 al expression. Drug Metab Dispos 2001;29:1074–1079.PubMedGoogle Scholar
  45. 45.
    Rinaldi AL, Morse MA, Fields HW, et al. Curcumin activates the aryl hydrocarbon receptor yet significantly inhibits (-)-benzo(a)pyrene-7R-trans-7,8-dihydrodiol bioactivation in oral squamous cell carcinoma cells and oral mucosa. Cancer Res 2002;62:5451–5456.PubMedGoogle Scholar
  46. 46.
    MacDonald CJ, Ciolino HP, Yeh GC. Dibenzoylmethane modulates aryl hydrocarbon receptor function and expression of cytochromes P50 1A1, 1 A2, and 1B1. Cancer Res 2001;61:3919–3924.PubMedGoogle Scholar
  47. 47.
    Hollman PC, Katan MB. Dietary flavonoids: intake, health effects and bioavailability. Food Chem Toxicol 1999;37:937–942.PubMedCrossRefGoogle Scholar
  48. 48.
    Yang CS, Landau JM, Huang MT, Newmark HL. Inhibition of carcinogenesis by dietary polyphenolic compounds. Annu Rev Nutr 2001;21:381–406.PubMedCrossRefGoogle Scholar
  49. 49.
    Yang M, Tanaka T, Hirose Y, et al. Chemopreventive effects of diosmin and hesperidin on N-butyl-N-(4- hydroxybutyl)nitrosamine-induced urinary-bladder carcinogenesis in male ICR mice. Int J Cancer 1997;73:719–724.PubMedCrossRefGoogle Scholar
  50. 50.
    Lautraite S, Musonda AC, Doehmer J, et al. Flavonoids inhibit genetic toxicity produced by carcinogens in cells expressing CYP 1 A2 and CYP 1 A 1. Mutagenesis 2001;17:45–53.CrossRefGoogle Scholar
  51. 51.
    Chae YH, Ho DK, Cassady JM, et al. Effects of synthetic and naturally occurring flavonoids on metabolic activation of benzo[a]pyrene in hamster embryo cell cultures. Chem Biol Interact 1992;82:181–193.PubMedCrossRefGoogle Scholar
  52. 52.
    Khanduja KL, Gandhi RK, Pathania V, Syal N. Prevention of N-nitrosodiethylamine-induced lung tumorigenesis by ellagic acid and quercetin in mice. Food Chem Toxicol 1999:37:313–318.PubMedCrossRefGoogle Scholar
  53. 53.
    Doostdar H, Burke MD, Mayer RT. Bioflavonoids: selective substrates and inhibitors for cytochrome P450 CYP 1 A and CYP 1 B 1. Toxicology 2000;144:31–38.PubMedCrossRefGoogle Scholar
  54. 54.
    Zhai S, Dai R, Wei X, et al. Inhibition of methoxyresorufin demethylase activity by flavonoids in human liver microsomes. Life Sci 1998;63:L119-L123.CrossRefGoogle Scholar
  55. 55.
    Kim BR, Kim DH, Park R, et al. Effect of an extract of the root of Scutellaria baicalensis and its flavonoids on aflatoxin B1 oxidizing cytochrome P450 enzymes. Planta Med 2001;67:396–399.PubMedCrossRefGoogle Scholar
  56. 56.
    Miranda CL, Yang YH, Henderson MC, et al. Prenylflavonoids from hops inhibit the metabolic activation of the carcinogenic heterocyclic amine 2-amino-3-methylimidazo[4, 5-f]quinoline, mediated by cDNA-expressed human CYP 1 A2. Drug Metab Dispos 2000;28:1297–1302.PubMedGoogle Scholar
  57. 57.
    Henderson MC, Miranda CL, Stevens JF, et al. In vitro inhibition of human P450 enzymes by prenylated flavonoids from hops, Humulus lupulus. Xenobiotica 2000;30:235–251.CrossRefGoogle Scholar
  58. 58.
    Ueng YF, Shyu CC, Lin YL, et al. Effects of baicalein and wogonin on drug-metabolizing enzymes in C57BL/6J mice. Life Sci 2000;67:2189–2200.PubMedCrossRefGoogle Scholar
  59. 59.
    Boobis AR, Nebert DW, Felton JS. Comparison of betanaphthoflavone and 3-methylcholanthrene as inducers of hepatic cytochrome(s) P-448 and aryl hydrocarbon (benzo[a]pyrene) hydroxylase activity. Mol Pharmacol 1977;13:259–268.PubMedGoogle Scholar
  60. 60.
    Nebert DW, Jensen NM, Shinozuka H, et al. The Ah phenotype. Survey of forty-eight rat strains and twenty inbred mouse strains. Genetics 1982;100:79–87.PubMedGoogle Scholar
  61. 61.
    Blank JA, Tucker AN, Sweatlock J, et al. alpha Naphthoflavone antagonism of 2,3,7,8-tetrachlorodibenzop-dioxin-induced murine lymphocyte ethoxyresorufin-O-deethylase activity and immunosuppression. Mol Pharmacol 1987;32:169–172.PubMedGoogle Scholar
  62. 62.
    Wattenberg L, Leong JL. Inhibition of the carcinogenic action of 7,12-dimethylbenz[a]anthracene by beta-naphthoflavone. Proc Soc Exp Biol Med 1968;128:940–943.Google Scholar
  63. 63.
    Malejka-Giganti D, Niehans GA, Reichert MA, Bliss RL. Post-initiation treatment of rats with indole-3-carbinol or beta-naphthoflavone does not suppress 7, 12-dimethylbenz[a]anthracene-induced mammary gland carcinogenesis. Cancer Lett 2000;160:209–218.PubMedCrossRefGoogle Scholar
  64. 64.
    Izzotti A, Camoirano A, Cartiglia C, et al. Patterns of DNA adduct formation in liver and mammary epithelial cells of rats treated with 7,12-dimethylbenz(a)anthracene, and selective effects of chemopreventive agents. Cancer Res 1999;59:4285–4290.PubMedGoogle Scholar
  65. 65.
    Im SH, Bolt MW, Stewart RK, Massey TE. Modulation of aflatoxin B1 biotransformation by beta-naphthoflavone in isolated rabbit lung cells. Arch Toxicol 1996;71:72–79.PubMedCrossRefGoogle Scholar
  66. 66.
    Gurtoo HL, Koser PL, Bansal SK, et al. Inhibition of aflatox-in B 1-hepatocarcinogenesis in rats by beta-naphthoflavone. Carcinogenesis 1985;6:675–678.PubMedCrossRefGoogle Scholar
  67. 67.
    Takahashi N, Harttig U, Williams DE, Bailey GS. The model Ah-receptor agonist beta-naphthoflavone inhibits aflatoxin B1-DNA binding in vivo in rainbow trout at dietary levels that do not induce CYP1A enzymes. Carcinogenesis 1996;17:79–87.PubMedCrossRefGoogle Scholar
  68. 68.
    Takahashi N, Miranda CL, Henderson MC, et al. Inhibition of in vitro aflatoxin B1-DNA binding in rainbow trout by CYP1A inhibitors: alpha-naphthoflavone, beta-naphthoflavone and trout CYP1A1 peptide antibody. Comp Biochem Physiol C Pharmacol Toxicol Endocrinol 1995;110:273–280.PubMedCrossRefGoogle Scholar
  69. 69.
    Mori H, Sugie S, Rahman W, Suzui N. Chemoprevention of 2-amino-1-methyl-6-phenylimidazo [4,5-b]pyridine-induced mammary carcinogenesis in rats. Cancer Lett 1999;143:195–198.PubMedCrossRefGoogle Scholar
  70. 70.
    DiGiovanni J, Slaga TJ, Viaje A, et al. The effects of 7,8-benzoflavone on skin-tumor initiating activities of various 7- and 12-substituted derivatives of 7,12-dimethylbenz[a]anthracene. J Nall Cancer Inst 1978;61:135–140.Google Scholar
  71. 71.
    Slaga TJ, Thompson S, Berry DL, et al. The effects of benzoflavones on polycyclic hydrocarbon metabolism and skin tumor initiation. Chem Biol Interact 1977;17:297–312.PubMedCrossRefGoogle Scholar
  72. 72.
    Kleiner HE, Vulimiri SV, Reed MJ, et al. Role of cytochrome P450 1 al and 1 b 1 in the metabolic activation of 7,12-dimethylbenz[a]anthracene and the effects of naturally occurring furanocoumarins on skin tumor initiation. Chem Res Toxicol 2002;15: 226–235.PubMedCrossRefGoogle Scholar
  73. 73.
    Kleiner HE, Reed MJ, DiGiovanni J. Naturally occurring coumarins inhibit human cytochromes P450 and block benzo[a]pyrene and 7,12-dimethylbenz[a]anthracene DNA adduct formation in MCF-7 cells. Chem Res Toxicol 2003 (in press).Google Scholar
  74. 74.
    Shimada T, Yamazaki H, Foroozesh M, et al. Selectivity of polycyclic inhibitors for human cytochrome P450s 1A1, 1A2, and 1B1. Chem Res Toxicol 1998;11:1048–1056.PubMedCrossRefGoogle Scholar
  75. 75.
    Shimada T, Gillam EM, Sutter TR, et al. Oxidation of xenobiotics by recombinant human cytochrome P450 1B1. Drug Metab Dispos 1997;25:617–622.PubMedGoogle Scholar
  76. 76.
    Merchant M, Arellano L, Safe S. The mechanisms of action of a-naphthoflavone as an inhibitor of 2,3,7,8-tetrachlorodibenzo-p-dioxin-induced CYP1A1 gene expression. Arch Biochem Biophys 1990;281:84–89.PubMedCrossRefGoogle Scholar
  77. 77.
    Ciolino HP, Daschner PJ, Yeh GC. Dietary flavonols quercetin and kaempferol are ligands of the aryl hydrocar-bon receptor that affect CYP1A1 transcription differentially. Biochem J 1999;340:715–722.PubMedCrossRefGoogle Scholar
  78. 78.
    Ciolino HP, Yeh GC. The flavonoid galangin is an inhibitor of CYP1A1 activity and an agonist/antagonist of the aryl hydrocarbon receptor. Br J Cancer 1999;79:1340–1346.PubMedCrossRefGoogle Scholar
  79. 79.
    Katiyar SK, Agarwal R, Wang ZY, et al. (-)-Epigallocatechin-3-gallate in Camellia sinensis leaves from Himalayan region of Sikkim: inhibitory effects against bio-chemical events and tumor initiation in Sencar mouse skin. Nutr Cancer 1992;18:73–83.PubMedCrossRefGoogle Scholar
  80. 80.
    Wang ZY, Cheng SJ, Zhou ZC, et al. Antimutagenic activity of green tea polyphenols. Mutat Res 1989;223:273–285.PubMedCrossRefGoogle Scholar
  81. 81.
    Wang ZY, Das M, Bickers DR, Mukhtar H. Interaction of epicatechins derived from green tea with rat hepatic cytochrome P-450. Drug Metab Dispos 1988;16:98–103.PubMedGoogle Scholar
  82. 82.
    Huang MT, Ho CT, Wang ZY, et al. Inhibitory effect of topical application of a green tea polyphenol fraction on tumor initiation and promotion in mouse skin. Carcinogenesis 1992;13:947–954.PubMedCrossRefGoogle Scholar
  83. 83.
    Kavanagh KT, Hafer LJ, Kim DW, et al. Green tea extracts decrease carcinogen-induced mammary tumor burden in rats and rate of breast cancer cell proliferation in culture. J Cell Biochem 2001;82:387–398.PubMedCrossRefGoogle Scholar
  84. 84.
    Vang O, Frandsen H, Hansen KT, et al. Modulation of drug-metabolising enzyme expression by condensation products of indole-3-ylcarbinol, an inducer in cruciferous vegetables. Pharmacol Toxicol 1999;84:59–65.PubMedCrossRefGoogle Scholar
  85. 85.
    Loub WD, Wattenberg LW, Davis DW. Aryl hydrocarbon hydroxylase induction in rat tissues by naturally occurring indoles of cruciferous plants. J Nall Cancer Inst 1975;54:985–988.Google Scholar
  86. 86.
    Bjeldanes LF, Kim JY, Grose KR, et al. Aromatic hydrocarbon responsiveness-receptor agonists generated from indole-3-carbinol in vitro and in vivo: comparisons with 2,3,7,8- tetrachlorodibenzo-p-dioxin. Proc Natl Acad Sci USA 1991;88:9543–9547.PubMedCrossRefGoogle Scholar
  87. 87.
    Kleman MI, Poellinger L, Gustafsson JA. Regulation of human dioxin receptor function by indolocarbazoles, receptor ligands of dietary origin. J Biol Chem 1994;269:5137–5144.PubMedGoogle Scholar
  88. 88.
    Stresser DM, Bjeldanes LF, Bailey GS, Williams DE. The anticarcinogen 3,3’-diindolylmethane is an inhibitor of cytochrome P-450. J Biochem Toxicol 1995;10:191–201.PubMedCrossRefGoogle Scholar
  89. 89.
    Stephensen PU, Bonnesen C, Schaldach C, et al. N-methoxyindole-3-carbinol is a more efficient inducer of cytochrome P- 450 1 A 1 in cultured cells than indol-3-carbinol. Nutr Cancer 2000;36:112–121.PubMedCrossRefGoogle Scholar
  90. 90.
    Chen YH, Riby J, Srivastava P, et al. Regulation of CYP 1 A 1 by indolo[3,2-b]carbazole in murine hepatoma cells. J Biol Chem 1995;270:22,548–22,555.Google Scholar
  91. 91.
    He YH, Friesen MD, Ruch RJ, Schut HA. Indole-3-carbinol as a chemopreventive agent in 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) carcinogenesis: inhibition of PhIP- DNA adduct formation, acceleration of PhIP metabolism, and induction of cytochrome P450 in female F344 rats. Food Chem Toxicol 2000;38:15–23.PubMedCrossRefGoogle Scholar
  92. 92.
    Grubbs CJ, Steele VE, Casebolt T, et al. Chemoprevention of chemically-induced mammary carcinogenesis by indole-3-carbinol. Anticancer Res 1995;15:709–716.PubMedGoogle Scholar
  93. 93.
    Tiwari RK, Guo L, Bradlow HL, et al. Selective responsiveness of human breast cancer cells to indole-3-carbinol, a chemopreventive agent. J Natl Cancer Inst 1994;86: 126–131.PubMedCrossRefGoogle Scholar
  94. 94.
    Stoner G, Casto B, Ralston S, et al. Development of a multi-organ rat model for evaluating chemopreventive agents: efficacy of indole-3carbinol. Carcino genesis 2002;23:265–272.CrossRefGoogle Scholar
  95. 95.
    Tiedink HG, Davies JA, Visser NA, et al. The stability of the nitrosated products of indole, indole-3-acetonitrile, indole-3-carbinol and 4-chloroindole. Food Chem Toxicol 1989;27:723–730.PubMedCrossRefGoogle Scholar
  96. 96.
    Sasagawa C, Matsushima T. Mutagen formation on nitrite treatment of indole compounds derived from indole-glucosinolate. Mutat Res 1991;250:169–174.PubMedCrossRefGoogle Scholar
  97. 97.
    Birt DF, Walker B, Tibbels MG, Bresnick E. Anti-mutagenesis and anti-promotion by apigenin, robinetin and indole-3-carbinol. Carcinogenesis 1986;7:959–963.PubMedCrossRefGoogle Scholar
  98. 98.
    Srivastava B, Shukla Y. Antitumour promoting activity of indole-3-carbinol in mouse skin carcinogenesis. Cancer Lett 1998;134:91–95.PubMedCrossRefGoogle Scholar
  99. 99.
    Lin JM, Amin S, Trushin N, Hecht SS. Effects of isothiocyanates on tumorigenesis by benzo[a]pyrene in murine tumor models. Cancer Lett 1993;74:151–159.PubMedCrossRefGoogle Scholar
  100. 100.
    Adam-Rodwell G, Morse MA, Stoner GD. The effects of phenethyl isothiocyanate on benzo[a]pyrene-induced tumors and DNA adducts in A/J mouse lung. Cancer Lett 1993;71: 35–42.PubMedCrossRefGoogle Scholar
  101. 101.
    Hecht SS. Inhibition of carcinogenesis by isothiocyanates. Drug Metab Rev 2000;32:395–411.PubMedCrossRefGoogle Scholar
  102. 102.
    Hecht S, Kenney P, Wang M, Upadhyaya P. Benzyl isothiocyanate: an effective inhibitor of polycyclic aromatic hydrocarbon tumorigenesis in A/J mouse lung. Cancer Lett 2002;187:87–94.PubMedCrossRefGoogle Scholar
  103. 103.
    Hecht SS, Kenney PM, Wang M, et al. Effects of phenethyl isothiocyanate and benzyl isothiocyanate, individually and in combination, on lung tumorigenesis induced in A/J mice by benzo[a]pyrene and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone. Cancer Lett 200;150:49–56.Google Scholar
  104. 104.
    Morse MA, Amin SG, Hecht SS, Chung FL. Effects of aromatic isothiocyanates on tumorigenicity, 06-methylguanine formation, and metabolism of the tobacco-specific nitrosamine 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in A/J mouse lung. Cancer Res 1989;49:2894–2897.PubMedGoogle Scholar
  105. 105.
    Morse MA, Reinhardt JC, Amin SG, et al. Effect of dietary aromatic isothiocyanates fed subsequent to the administration of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone on lung tumorigenicity in mice. Cancer Lett 1990;49:225–230.PubMedCrossRefGoogle Scholar
  106. 106.
    Sticha KR, Kenney PM, Boysen G, et al. Effects of benzyl isothiocyanate and phenethyl isothiocyanate on DNA adduct formation by a mixture of benzo[a]pyrene and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in A/J mouse lung. Carcinogenesis 2002;23:1433–1439.PubMedCrossRefGoogle Scholar
  107. 107.
    Goosen TC, Kent UM, Brand L, Hollenberg PF. Inactivation of cytochrome P450 2B 1 by benzyl isothiocyanate, a chemopreventative agent from cruciferous vegetables. Chem Res Toxicol 2000;13:1349–1359.PubMedCrossRefGoogle Scholar
  108. 108.
    Kent UM, Juschyshyn MI, Hollenberg PF. Mechanism-based inactivators as probes of cytochrome P450 structure and function. Curr Drug Metab 2001;2:215–243.PubMedCrossRefGoogle Scholar
  109. 109.
    Guo Z, Smith TJ, Wang E, et al. 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 1993;14: 1167–1173.PubMedCrossRefGoogle Scholar
  110. 110.
    Smith TJ, Guo Z, Li C, et al. Mechanisms of inhibition of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone bioactivation in mouse by dietary phenethyl isothiocyanate. Cancer Res 1993;53:3276–3282.PubMedGoogle Scholar
  111. 111.
    Smith TJ, Guo Z, Guengerich FP, Yang CS. Metabolism of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) by human cytochrome P450 1A2 and its inhibition by phenethyl isothiocyanate. Carcinogenesis 1996;17:809–813.PubMedCrossRefGoogle Scholar
  112. 112.
    Guo Z, Smith TJ, Wang E, et al. Effects of phenethyl isothiocyanate, a carcinogenesis inhibitor, on xenobioticmetabolizing enzymes and nitrosamine metabolism in rats. Carcinogenesis 1992;13:2205–2210.PubMedCrossRefGoogle Scholar
  113. 113.
    Murray RDH, Mendez J, Brown SA, eds. The Natural Coumarins: Occurrence, Chemistry and Biochemistry. John Wiley & Sons, Ltd., New York, 1982, pp.97–111.Google Scholar
  114. 114.
    Robinson T. Aromatic compound, in The Organic Constituents of Higher Plants: Their Chemistry and Interrelationships. Robinson T, ed. Burgess Publishing Co., Minneapolis, MN, 1967, pp.47–76.Google Scholar
  115. 115.
    Stanley W, Jurd L. Citrus coumarins. J Agr Food Chem 1971;19:1106–1110.CrossRefGoogle Scholar
  116. 116.
    Okuyama T, Takata M, Nishino H, et al. Studies on the antitumor-promoting activity of naturally occurring substances. II. Inhibition of tumor-promoter-enhanced phospholipid metabolism by umbelliferous materials. Chem Pharm Bull(Tokyo) 1990;38:1084–1086.CrossRefGoogle Scholar
  117. 117.
    Stupans I, Ryan A. In vitro inhibition of 3-methylcholanthrene-induced rat hepatic acyl hydrocarbon hydroxylase by 8-acyl-7-hydroxycoumarins. Biochem Pharmacol 1984;33:131–139.PubMedCrossRefGoogle Scholar
  118. 118.
    Woo W, Shin K, Lee C. Effect of naturally occurring coumarins on the activity of drug metabolizing enzyme. Biochem Pharmacol 1983;32:1800–1803.PubMedCrossRefGoogle Scholar
  119. 119.
    Wall ME, Wani MC, Hughes TJ, Taylor H. Plant antimutagens, in Antimutagenesis and AnticarcinogenesisMechanismII. Karuda Y, Shankel DM, Walters MD, eds. Plenum Press, New York, 1990, pp. 61–78.CrossRefGoogle Scholar
  120. 120.
    Fouin-Fortunet H, Tinel M, Descatoire V, et al. Inactivation of cytochrome P450 by the drug methoxsalen. J Pharmacol Exp Ther 1986:236:237–247.PubMedGoogle Scholar
  121. 121.
    Letteron P, Descatoire V, Larrey D, et al. Inactivation and induction of cytochrome P450 by various psoralen derivatives in rats. J Pharmacol Exp Ther 1986;238:685–692.PubMedGoogle Scholar
  122. 122.
    Mays D, Nawoot S, Hilliard J, et al. Inhibition and induction of drug biotransformation in vivo by 8-methoxypsoralen: studies of caffeine, phenytoin and hexobarbital metabolism in the rat. J Pharmacol Exp Ther 1987;243:227–233.PubMedGoogle Scholar
  123. 123.
    Apseloff G, Sheppard D, Chambers M, et al. Inhibition and induction of theophylline metabolism by 8-methoxypsoralen: in vivo study in rats and humans. Drug Metabol Dispos 1990;18:298–303.Google Scholar
  124. 124.
    Tsamboas D, Vizethum W, Goerz G. Effect of oral 8-methoxypsoralen on rat liver microsomal cytochrome P-450. Arch Dermatol Res 1978;263:339–342.CrossRefGoogle Scholar
  125. 125.
    Bickers D, Mukhtar H, Molica S, Pathak M. The effect of psoralens on hepatic and cutaneous drug metabolizing enzymes and cytochrome P450. J Investig Dermatol 1982;79:201–205.PubMedCrossRefGoogle Scholar
  126. 126.
    Mays D, Hilliard J, Wong D, Gerber N. Activation of 8-methoxypsoralen by cytochromes P-450 enzyme kinetics of covalent binding and influence of inhibitors and inducers of drug metabolism. Biochem Pharmacol 1989;38:1647–1655.PubMedCrossRefGoogle Scholar
  127. 127.
    Mays D, Hilliard J, Wong D, et al. Bioactivation of 8-methoxypsoralen and irreversible inactivation of cytochrome P450 in mouse liver microsomes: modification by monoclonal antibodies, inhibition of drug metabolism and distribution of covalent adducts. J Pharmacol Exp Ther 1990;254:720–731.PubMedGoogle Scholar
  128. 128.
    Ashwood-Smith MJ, Warrington PJ, Jenins M, et al. Photobiological properties of a novel, naturally occurring furoisocoumarin, coriandrin. Photochem Photobiol 1989;50: 745–751.PubMedCrossRefGoogle Scholar
  129. 129.
    He K, Iyer KR, Hayes RN, et al. Inactivation of cytochrome P450 3A4 by bergamottin, a component of grapefruit juice. Chem Res Toxicol 1998;11:252–259.PubMedCrossRefGoogle Scholar
  130. 130.
    Koenigs LL, Trager WF. Mechanism-based inactivation of P450 2A6 by furanocoumarins. Biochemistry 1998;37: 10,047–10,061.Google Scholar
  131. 131.
    Koenigs LL, Trager WF. Mechanism-based inactivation of cytochrome P450 2B1 by 8-methoxypsoralen and several other furanocoumarins. Biochemistry 1998;37:13,184–13,193.Google Scholar
  132. 132.
    Maenpaa J, Sigusch H, Raunio H, et al. Differential inhibition of coumarin 7-hydroxylase activity in mouse and human liver microsomes. Biochem Pharm 1993;45:1035–1042.PubMedCrossRefGoogle Scholar
  133. 133.
    Feuer G, Kellen J. Inhibition and enhancement of mammary tumorigenesis by 7,12-dimethylbenz (a)anthracene in the female Sprague-Dawley rat. Int J Clin Pharmacol 1974;9:62–69.PubMedGoogle Scholar
  134. 134.
    Feuer G, Kellen JA, Kovacs K. Suppression of 7,12-dimethylbenzo(a)anthracene-induced breast carcinoma by coumarin in the rat. Oncology(Basel) 1976;33:35–39.CrossRefGoogle Scholar
  135. 135.
    Sparnins V, Wattenberg L. 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 1981;66: 769–771.PubMedGoogle Scholar
  136. 136.
    Kelly VP, Ellis EM, Manson MM, et al. Chemoprevention of aflatoxin B1 hepatocarcinogenesis by coumarin, a natural benzopyrone that is a potent inducer of aflatoxin B1-aldehyde reductase, the glutathione S-transferase A5 and P1 subunits, and NAD(P)H:quinone oxidoreductase in rat liver. Cancer Res 2000;60:957–969.PubMedGoogle Scholar
  137. 137.
    Cai Y, Kleiner H, Johnston D, et al. Effect of naturally occurring coumarins on the formation of epidermal DNA adducts and skin tumors induced by benzo[a]pyrene and 7,12-dimethylbenz[a]anthracene in SENCAR mice. Carcinogenesis 1997;18:1521–1527.PubMedCrossRefGoogle Scholar
  138. 138.
    Cai Y- N, Baer-Dubowska W, Ashwood-Smith M, DiGiovanni J. Inhibitory effects of naturally occurring coumarins on the metabolic activation of benzo[a]pyrene and 7,12-dimethylbenz[a]anthracene in cultured mouse keratinocytes. Carcinogenesis 1997;18:215–222.PubMedCrossRefGoogle Scholar
  139. 139.
    Pottenger L, Jefcoate C. Characterization of a novel cytochrome P450 from the transformable cell line, C3H/10T1/2. Carcinogenesis 1990;11:321–327.PubMedCrossRefGoogle Scholar
  140. 140.
    Kleiner HE, Vulimiri SV, Miller L, et al. Oral administration of naturally occurring coumarins leads to altered phase I and II enzyme activities and reduced DNA adduct formation by polycyclic aromatic hydrocarbons in various tissues of SENCAR mice. Carcinogenesis 2001;22:73–82.PubMedCrossRefGoogle Scholar
  141. 141.
    Kleiner HE, Vulimiri SV, Starost MF, et al. Oral administration of the citrus coumarin, isopimpinellin, blocks DNA adduct formation and skin tumor initiation by 7,12-dimethylbenz[a]anthracene in SENCAR mice. Carcinogenesis 2002;23:1667–1675.PubMedCrossRefGoogle Scholar
  142. 142.
    Miller EG, McWhorter K, Rivera-Hidalgo F, et al. Kahweol and cafestol: inhibitors of hamster buccal pouch carcinogenesis. Nutr Cancer 1991;15:41–46.PubMedCrossRefGoogle Scholar
  143. 143.
    Cavin C, Holzhauser D, Constable A, et al. The coffeespecific diterpenes cafestol and kahweol protect against aflatoxin B1-induced genotoxicity through a dual mechanism. Carcinogenesis 1998;19:1369–1375.PubMedCrossRefGoogle Scholar
  144. 144.
    Cavin C, Mace K, Offord EA, Schilter B. Protective effects of coffee diterpenes against aflatoxin B1-induced genotoxicity: mechanisms in rat and human cells. Food Chem Toxicol 2001;39:549–556.PubMedCrossRefGoogle Scholar
  145. 145.
    Urgert R, Katan MB. The cholesterol-raising factor from coffee beans. J R Soc Med 1996;89:618–623.PubMedGoogle Scholar
  146. 146.
    de Roos B, Katan MB. Possible mechanisms underlying the cholesterol-raising effect of the coffee diterpene cafestol. Curr Opin Lipidol 1999;10:41–45.PubMedCrossRefGoogle Scholar
  147. 147.
    Terpstra AHM, Katan MB, Weusten van der Wouw B, et al. The hypercholesterolemic effect of cafestol in coffee oil in gerbils and rats. J Nutr Biochem 2000;11:311–317.PubMedCrossRefGoogle Scholar
  148. 148.
    Huang MT, Ho CT, Wang ZY, et al. Inhibition of skin tumorigenesis by rosemary and its constituents carnosol and ursolic acid. Cancer Res 1994;54:701–708.PubMedGoogle Scholar
  149. 149.
    Singletary K, MacDonald C, Wallig M. Inhibition by rosemary and carnosol of 7,12-dimethylbenz[a]anthracene (DMBA)-induced rat mammary tumorigenesis and in vivo DMBA-DNA adduct formation. Cancer Lett 1996;104:43–48.PubMedCrossRefGoogle Scholar
  150. 150.
    Offord EA, Mace K, Ruffieux C, et al. Rosemary components inhibit benzo[a]pyrene-induced genotoxicity in human bronchial cells. Carcinogenesis 1995;16:2057–2062.PubMedCrossRefGoogle Scholar
  151. 151.
    Debersac P, Heydel JM, Amiot MJ, et al. Induction of cytochrome P450 and/or detoxication enzymes by various extracts of rosemary: description of specific patterns. Food Chem Toxicol 2001;39:907–918.PubMedCrossRefGoogle Scholar
  152. 152.
    Viaje A, Jui-yun L, Hopkins NE, et al. Inhibition of the binding of 7,12-dimethylbenz[a]anthracene and benzo[a]pyrene to DNA in mouse epidermis by aryl acetylates. Carcinogenesis 1990;11:1139–1143.PubMedCrossRefGoogle Scholar
  153. 153.
    DiGiovanni J, Slaga TJ, Juchau MR. Inhibitory effects of environmental chemicals on polycyclic aromatic hydrocarbon in carcinogenesis, in Carcinogenesis, Modifiers of Chemical Carcinogenesis, Vol. 5. Raven Press, New York, 1980, pp.145–168.Google Scholar
  154. 154.
    DiGiovanni J, Slaga TJ. Modification of polycyclic aromatic hydrocarbon carcinogenesis, in Polycyclic Hydrocarbons and Cancer, Vol. 3. Gelboin HV, Tso POP, eds. Academic Press, New York, 1981, pp.259–292.Google Scholar
  155. 155.
    Slaga TJ, DiGiovanni J. Inhibition of carcinogenesis, in Chemical Carcinogens, Vol. II. Searle CE, ed. ACS Monograph, 1984, pp.1279–1321.Google Scholar
  156. 156.
    DiGiovanni J. Inhibition of chemical carcinogenesis, in Handbook of Experimental Pharmacology, Part II: Carcinogenesis and Mutagenesis. Grover PL, Cooper CS, eds. Springer Verlag, Heidelberg, Germany, 1990, pp.159–332.CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2004

Authors and Affiliations

  • John DiGiovanni
  • Heather E. Kleiner

There are no affiliations available

Personalised recommendations