Harman induces CYP1A1 enzyme through an aryl hydrocarbon receptor mechanism

Toxicology and Applied Pharmacology

Volumn 249, Issue 1, 2010, Pages 55-64

  El Gendy, Mohamed A M ^a   El Kadi, Ayman O S ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

Aryl hydrocarbon receptor ligand; Carcinogenesis; CYP1A1; Harman

Indexed keywords

AROMATIC HYDROCARBON RECEPTOR; CYTOCHROME P450 1A1; DACTINOMYCIN; HARMAN; LUCIFERASE; MESSENGER RNA; RESVERATROL; SMALL INTERFERING RNA; HARMINE; PROTEIN BINDING;

ANIMAL CELL; ARTICLE; CANCER CELL CULTURE; CELL VIABILITY; CONTROLLED STUDY; ENZYME ACTIVITY; ENZYME INHIBITION; GEL MOBILITY SHIFT ASSAY; GENETIC TRANSCRIPTION; HEPATOMA CELL; HUMAN; HUMAN CELL; NONHUMAN; PROTEIN PROCESSING; RAT; SIGNAL TRANSDUCTION; ANALOGS AND DERIVATIVES; ANIMAL; BIOSYNTHESIS; CELL SURVIVAL; COMPARATIVE STUDY; DOSE RESPONSE; DRUG EFFECTS; ENZYME INDUCTION; GUINEA PIG; HEPG2 CELL LINE; MALE; METABOLISM; PHYSIOLOGY; TUMOR CELL LINE;

ANIMALS; CELL LINE, TUMOR; CELL SURVIVAL; CYTOCHROME P-450 CYP1A1; DOSE-RESPONSE RELATIONSHIP, DRUG; ENZYME INDUCTION; GUINEA PIGS; HARMINE; HEP G2 CELLS; HUMANS; MALE; PROTEIN BINDING; RATS; RECEPTORS, ARYL HYDROCARBON;

RATTUS;

EID: 77957885625     PISSN: 0041008X     EISSN: 10960333     Source Type: Journal    
DOI: 10.1016/j.taap.2010.08.014     Document Type: Article

References (45)

1. Abdelrahim M., Smith R., Safe S. Aryl hydrocarbon receptor gene silencing with small inhibitory RNA differentially modulates Ah-responsiveness in MCF-7 and HepG2 cancer cells. Mol. Pharmacol. 2003, 63:1373-1381.
2. Amakura Y., Tsutsumi T., Sasaki K., Yoshida T., Maitani T. Screening of the inhibitory effect of vegetable constituents on the aryl hydrocarbon receptor-mediated activity induced by 2, 3, 7, 8-tetrachlorodibenzo-p-dioxin. Biol. Pharm. Bull. 2003, 26:1754-1760.
3. Ancolio C., Azas N., Mahiou V., Ollivier E., Di Giorgio C., Keita A., Timon-David P., Balansard G. Antimalarial activity of extracts and alkaloids isolated from six plants used in traditional medicine in Mali and Sao Tome. Phytother. Res. 2002, 16:646-649.
4. Androutsopoulos V.P., Tsatsakis A.M., Spandidos D.A. Cytochrome P450 CYP1A1: wider roles in cancer progression and prevention. BMC Cancer 2009, 9:187.
5. Anwar-Mohamed A., El-Kadi A.O. Down-regulation of the carcinogen-metabolizing enzyme cytochrome P450 1a1 by vanadium. Drug Metab. Dispos. 2008, 36:1819-1827.
6. Anwar-Mohamed A., El-Kadi A.O. Sulforaphane induces CYP1A1 mRNA, protein, and catalytic activity levels via an AhR-dependent pathway in murine hepatoma Hepa 1c1c7 and human HepG2 cells. Cancer Lett. 2009, 275:93-101.
7. Balon M., Munoz M.A., Carmona C., Guardado P., Galan M. A fluorescence study of the molecular interactions of harmane with the nucleobases, their nucleosides and mononucleotides. Biophys. Chem. 1999, 80:41-52.
8. Boeira J.M., da Silva J., Erdtmann B., Henriques J.A. Genotoxic effects of the alkaloids harman and harmine assessed by comet assay and chromosome aberration test in mammalian cells in vitro. Pharmacol. Toxicol. 2001, 89:287-294.
9. Boeira J.M., Viana A.F., Picada J.N., Henriques J.A. Genotoxic and recombinogenic activities of the two beta-carboline alkaloids harman and harmine in Saccharomyces cerevisiae. Mutat. Res. 2002, 500:39-48.
10. Bohonowych J.E., Zhao B., Timme-Laragy A., Jung D., Di Giulio R.T., Denison M.S. Newspapers and newspaper ink contain agonists for the ah receptor. Toxicol. Sci. 2008, 102:278-290.
11. Bradshaw T.D., Trapani V., Vasselin D.A., Westwell A.D. The aryl hydrocarbon receptor in anticancer drug discovery: friend or foe?. Curr. Pharm. Des. 2002, 8:2475-2490.
12. Denison M.S., Nagy S.R. Activation of the aryl hydrocarbon receptor by structurally diverse exogenous and endogenous chemicals. Annu. Rev. Pharmacol. Toxicol. 2003, 43:309-334.
13. Denison M.S., Pandini A., Nagy S.R., Baldwin E.P., Bonati L. Ligand binding and activation of the Ah receptor. Chem Biol Interact 2002, 141:3-24.
14. Dertinger S.D., Nazarenko D.A., Silverstone A.E., Gasiewicz T.A. Aryl hydrocarbon receptor signaling plays a significant role in mediating benzo[a]pyrene- and cigarette smoke condensate-induced cytogenetic damage in vivo. Carcinogenesis 2001, 22:171-177.
15. El Gendy M.A., El-Kadi A.O. Peganum harmala L. differentially modulates cytochrome P450 gene expression in human hepatoma HepG2 cells. Drug Metab. Lett. 2009, 3:212-216.
16. El Gendy M.A., Somayaji V., El-Kadi A.O. Peganum harmala L. is a candidate herbal plant for preventing dioxin mediated effects. Planta Med. 2010, 76:671-677.
17. Elbekai R.H., El-Kadi A.O. Transcriptional activation and posttranscriptional modification of Cyp1a1 by arsenite, cadmium, and chromium. Toxicol. Lett. 2007, 172:106-119.
18. Funayama Y., Nishio K., Wakabayashi K., Nagao M., Shimoi K., Ohira T., Hasegawa S., Saijo N. Effects of beta- and gamma-carboline derivatives of DNA topoisomerase activities. Mutat. Res. 1996, 349:183-191.
19. Herraiz T. Relative exposure to beta-carbolines norharman and harman from foods and tobacco smoke. Food Addit. Contam. 2004, 21:1041-1050.
20. Herraiz T. Identification and occurrence of beta-carboline alkaloids in raisins and inhibition of monoamine oxidase (MAO). J. Agric. Food Chem. 2007, 55:8534-8540.
21. Herraiz T., Chaparro C. Human monoamine oxidase enzyme inhibition by coffee and beta-carbolines norharman and harman isolated from coffee. Life Sci. 2006, 78:795-802.
22. Herraiz T., Guillen H., Aran V.J. Oxidative metabolism of the bioactive and naturally occurring beta-carboline alkaloids, norharman and harman, by human cytochrome P450 enzymes. Chem. Res. Toxicol. 2008, 21:2172-2180.
23. Hummerich J., Zohm C., Pfau W. Modulation of cytochrome P450 1A1 by food-derived heterocyclic aromatic amines. Toxicology 2004, 199:231-240.
24. Kuhn W., Muller T., Grosse H., Rommelspacher H. Elevated levels of harman and norharman in cerebrospinal fluid of parkinsonian patients. J. Neural Transm. 1996, 103:1435-1440.
25. Levitt R.C., Legraverend C., Nebert D.W., Pelkonen O. Effects of harman and norharman on the mutagenicity and binding to DNA of benzo[a]pyrene metabolites in vitro and on aryl hydrocarbon hydroxylase induction in cell culture. Biochem. Biophys. Res. Commun. 1977, 79:1167-1175.
26. Lorenzen A., Kennedy S.W. A fluorescence-based protein assay for use with a microplate reader. Anal. Biochem. 1993, 214:346-348.
27. Louis E.D., Pellegrino K.M., Factor-Litvak P., Rios E., Jiang W., Henchcliffe C., Zheng W. Cancer and blood concentrations of the comutagen harmane in essential tremor. Mov. Disord. 2008, 23:1747-1751.
28. Ma Q., Lu A.Y. CYP1A induction and human risk assessment: an evolving tale of in vitro and in vivo studies. Drug Metab. Dispos. 2007, 35:1009-1016.
29. Madle E., Obe G., Hansen J., Ristow H. Harman and norharman: induction of sister-chromatid exchanges in human peripheral lymphocytes in vitro and interaction with isolated DNA. Mutat. Res. 1981, 90:433-442.
30. Mandal P.K. Dioxin: a review of its environmental effects and its aryl hydrocarbon receptor biology. J. Comp. Physiol. B 2005, 175:221-230.
31. Matsumura F. On the significance of the role of cellular stress response reactions in the toxic actions of dioxin. Biochem. Pharmacol. 2003, 66:527-540.
32. Mikstacka R., Baer-Dubowska W., Wieczorek M., Sobiak S. Thiomethylstilbenes as inhibitors of CYP1A1, CYP1A2 and CYP1B1 activities. Mol. Nutr. Food Res. 2008, 52(Suppl 1):S77-S83.
33. Nii H. Possibility of the involvement of 9H-pyrido[3, 4-b]indole (norharman) in carcinogenesis via inhibition of cytochrome P450-related activities and intercalation to DNA. Mutat. Res. 2003, 541:123-136.
34. Pfau W., Skog K. Exposure to beta-carbolines norharman and harman. J. Chromatogr. B Anal. Technol. Biomed. Life Sci. 2004, 802:115-126.
35. Shah P.P., Saurabh K., Pant M.C., Mathur N., Parmar D. Evidence for increased cytochrome P450 1A1 expression in blood lymphocytes of lung cancer patients. Mutat. Res. 2009, 670:74-78.
36. Shimada T., Fujii-Kuriyama Y. Metabolic activation of polycyclic aromatic hydrocarbons to carcinogens by cytochromes P450 1A1 and 1B1. Cancer Sci. 2004, 95:1-6.
37. Skog K., Solyakov A., Arvidsson P., Jagerstad M. Analysis of nonpolar heterocyclic amines in cooked foods and meat extracts using gas chromatography-mass spectrometry. J. Chromatogr. A 1998, 803:227-233.
38. Slattery M.L., Samowtiz W., Ma K., Murtaugh M., Sweeney C., Levin T.R., Neuhausen S. CYP1A1, cigarette smoking, and colon and rectal cancer. Am. J. Epidemiol. 2004, 160:842-852.
39. Solyakov A., Skog K. Screening for heterocyclic amines in chicken cooked in various ways. Food Chem. Toxicol. 2002, 40:1205-1211.
40. Totsuka Y., Takamura-Enya T., Nishigaki R., Sugimura T., Wakabayashi K. Mutagens formed from beta-carbolines with aromatic amines. J. Chromatogr. B Anal. Technol. Biomed. Life Sci. 2004, 802:135-141.
41. Tsuchiya H., Sato M., Watanabe I. Antiplatelet activity of soy sauce as functional seasoning. J. Agric. Food Chem. 1999, 47:4167-4174.
42. Yamashita K., Ohgaki H., Wakabayashi K., Nagao M., Sugimura T. DNA adducts formed by the comutagens harman and norharman in various tissues of mice. Cancer Lett. 1988, 42:179-183.
43. Yoshida R., Ogawa Y. Oxidative stress induced by 2, 3, 7, 8-tetrachlorodibenzo-p-dioxin: an application of oxidative stress markers to cancer risk assessment of dioxins. Ind. Health 2000, 38:5-14.
44. Zheng W., Wang S., Barnes L.F., Guan Y., Louis E.D. Determination of harmane and harmine in human blood using reversed-phased high-performance liquid chromatography and fluorescence detection. Anal. Biochem. 2000, 279:125-129.
45. Zordoky B.N., Anwar-Mohamed A., Aboutabl M.E., El-Kadi A.O. Acute doxorubicin cardiotoxicity alters cardiac cytochrome P450 expression and arachidonic acid metabolism in rats. Toxicol. Appl. Pharmacol. 2010, 242:38-46.