Transcriptional and posttranslational inhibition of dioxin-mediated induction of CYP1A1 by harmine and harmol

Toxicology Letters

Volumn 208, Issue 1, 2012, Pages 51-61

  El Gendy, Mohamed A M ^a   Soshilov, Anatoly A ^b   Denison, Michael S ^b   El Kadi, Ayman O S ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Aryl hydrocarbon receptor; Carcinogenesis; CYP 1A1; Harmine; Harmol

Indexed keywords

CYTOCHROME P450 1A1; DIOXIN; HARMINE; HARMOL; LUCIFERASE; MESSENGER RNA;

ANIMAL CELL; ARTICLE; CARCINOGENESIS; CELL VIABILITY; CONTROLLED STUDY; ENVIRONMENTAL EXPLOITATION; ENZYME ACTIVITY; ENZYME INDUCTION; ENZYME MECHANISM; GEL MOBILITY SHIFT ASSAY; HEPATOMA CELL; HUMAN; LIGAND BINDING; MALE; MOUSE; NONHUMAN; PRIORITY JOURNAL; PROTEIN ANALYSIS; PROTEIN FUNCTION; PROTEIN PROCESSING;

ANIMALS; CARCINOGENS; CYTOCHROME P-450 CYP1A1; DIOXINS; GENE EXPRESSION; GUINEA PIGS; HARMINE; HEP G2 CELLS; HUMANS; MICE; MICE, INBRED C57BL; MONOAMINE OXIDASE INHIBITORS; PROTEIN BIOSYNTHESIS; TRANSCRIPTION, GENETIC;

MURINAE;

EID: 80155184828     PISSN: 03784274     EISSN: 18793169     Source Type: Journal    
DOI: 10.1016/j.toxlet.2011.09.030     Document Type: Article

References (39)

1. 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.
2. Arshad N., Zitterl-Eglseer K., Hasnain S., Hess M. Effect of Peganum harmala or its beta-carboline alkaloids on certain antibiotic resistant strains of bacteria and protozoa from poultry. Phytother. Res. 2008, 22:1533-1538.
3. Bradshaw T.D., Bell D.R. Relevance of the aryl hydrocarbon receptor (AhR) for clinical toxicology. Clin. Toxicol. (Phila) 2009, 47:632-642.
4. Cao R., Chen H., Peng W., Ma Y., Hou X., Guan H., Liu X., Xu A. Design, synthesis and in vitro and in vivo antitumor activities of novel beta-carboline derivatives. Eur. J. Med. Chem. 2005, 40:991-1001.
5. Cao R., Peng W., Chen H., Ma Y., Liu X., Hou X., Guan H., Xu A. DNA binding properties of 9-substituted harmine derivatives. Biochem. Biophys. Res. Commun. 2005, 338:1557-1563.
6. Cao R., Peng W., Wang Z., Xu A. Beta-carboline alkaloids: biochemical and pharmacological functions. Curr. Med. Chem. 2007, 14:479-500.
7. Denison M.S., Harper P.A., Okey A.B. Ah receptor for 2,3,7,8-tetrachlorodibenzo-p-dioxin. Codistribution of unoccupied receptor with cytosolic marker enzymes during fractionation of mouse liver, rat liver and cultured Hepa-1c1 cells. Eur. J. Biochem. 1986, 155:223-229.
8. 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.
9. 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.
10. 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.
11. Di Giorgio C., Delmas F., Ollivier E., Elias R., Balansard G., Timon-David P. In vitro activity of the beta-carboline alkaloids harmane, harmine, and harmaline toward parasites of the species Leishmania infantum. Exp. Parasitol. 2004, 106:67-74.
12. 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.
13. El Gendy M.A., El-Kadi A.O. Harman induces CYP1A1 enzyme through an aryl hydrocarbon receptor mechanism. Toxicol. Appl. Pharmacol. 2010, 249:55-64.
14. 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.
15. Herraiz T., Gonzalez D., Ancin-Azpilicueta C., Aran V.J., Guillen H. Beta-carboline alkaloids in Peganum harmala and inhibition of human monoamine oxidase (MAO). Food Chem. Toxicol. 2010, 48:839-845.
16. Im J.H., Jin Y.R., Lee J.J., Yu J.Y., Han X.H., Im S.H., Hong J.T., Yoo H.S., Pyo M.Y., Yun Y.P. Antiplatelet activity of beta-carboline alkaloids from Perganum harmala: a possible mechanism through inhibiting PLCgamma2 phosphorylation. Vasc. Pharmacol. 2009, 50:147-152.
17. Lorenzen A., Kennedy S.W. A fluorescence-based protein assay for use with a microplate reader. Anal. Biochem. 1993, 214:346-348.
18. Mandal P.K. Dioxin: a review of its environmental effects and its aryl hydrocarbon receptor biology. J. Comp. Physiol. B 2005, 175:221-230.
19. Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J. Immunol. Methods 1983, 65:55-63.
20. Moura D.J., Richter M.F., Boeira J.M., Pegas Henriques J.A., Saffi J. Antioxidant properties of beta-carboline alkaloids are related to their antimutagenic and antigenotoxic activities. Mutagenesis 2007, 22:293-302.
21. Murray I.A., Flaveny C.A., DiNatale B.C., Chairo C.R., Schroeder J.C., Kusnadi A., Perdew G.H. Antagonism of aryl hydrocarbon receptor signaling by 6,2',4'-trimethoxyflavone. J. Pharmacol. Exp. Ther. 2010, 332:135-144.
22. Pollenz R.S. Specific blockage of ligand-induced degradation of the Ah receptor by proteasome but not calpain inhibitors in cell culture lines from different species. Biochem. Pharmacol. 2007, 74:131-143.
23. Puppala D., Lee H., Kim K.B., Swanson H.I. Development of an aryl hydrocarbon receptor antagonist using the proteolysis-targeting chimeric molecules approach: a potential tool for chemoprevention. Mol. Pharmacol. 2008, 73:1064-1071.
24. Revel A., Raanani H., Younglai E., Xu J., Rogers I., Han R., Savouret J.F., Casper R.F. Resveratrol, a natural aryl hydrocarbon receptor antagonist, protects lung from DNA damage and apoptosis caused by benzo[a]pyrene. J. Appl. Toxicol. 2003, 23:255-261.
25. Samoylenko V., Rahman M.M., Tekwani B.L., Tripathi L.M., Wang Y.H., Khan S.I., Khan I.A., Miller L.S., Joshi V.C., Muhammad I. Banisteriopsis caapi, a unique combination of MAO inhibitory and antioxidative constituents for the activities relevant to neurodegenerative disorders and Parkinson's disease. J. Ethnopharmacol. 2010, 127:357-367.
26. 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.
27. 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.
28. Signorelli P., Ghidoni R. Resveratrol as an anticancer nutrient: molecular basis, open questions and promises. J. Nutr. Biochem. 2005, 16:449-466.
29. Sinal C.J., Bend J.R. Aryl hydrocarbon receptor-dependent induction of cyp1a1 by bilirubin in mouse hepatoma hepa 1c1c7 cells. Mol. Pharmacol. 1997, 52:590-599.
30. 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.
31. Song Y., Kesuma D., Wang J., Deng Y., Duan J., Wang J.H., Qi R.Z. Specific inhibition of cyclin-dependent kinases and cell proliferation by harmine. Biochem. Biophys. Res. Commun. 2004, 317:128-132.
32. Suzuki T., Nohara K. Regulatory factors involved in species-specific modulation of arylhydrocarbon receptor (AhR)-dependent gene expression in humans and mice. J. Biochem. 2007, 142:443-452.
33. Taguchi K., Motohashi H., Yamamoto M. Molecular mechanisms of the Keap1-Nrf2 pathway in stress response and cancer evolution. Genes Cells 2011, 16:123-140.
34. Wiseman S.B., Vijayan M.M. Aryl hydrocarbon receptor signaling in rainbow trout hepatocytes: role of hsp90 and the proteasome. Comp. Biochem. Physiol. C: Toxicol. Pharmacol. 2007, 146:484-491.
35. Yu A.M., Idle J.R., Krausz K.W., Kupfer A., Gonzalez F.J. Contribution of individual cytochrome P450 isozymes to the O-demethylation of the psychotropic beta-carboline alkaloids harmaline and harmine. J. Pharmacol. Exp. Ther. 2003, 305:315-322.
36. Zhang S., Qin C., Safe S.H. Flavonoids as aryl hydrocarbon receptor agonists/antagonists: effects of structure and cell context. Environ. Health Perspect. 2003, 111:1877-1882.
37. Zhao B., Degroot D.E., Hayashi A., He G., Denison M.S. CH223191 is a ligand-selective antagonist of the Ah (Dioxin) receptor. Toxicol. Sci. 2010, 117:393-403.
38. Zhou J., Gasiewicz T.A. 3'-methoxy-4'-nitroflavone, a reported aryl hydrocarbon receptor antagonist, enhances Cyp1a1 transcription by a dioxin responsive element-dependent mechanism. Arch. Biochem. Biophys. 2003, 416:68-80.
39. Zhou J.G., Henry E.C., Palermo C.M., Dertinger S.D., Gasiewicz T.A. Species-specific transcriptional activity of synthetic flavonoids in guinea pig and mouse cells as a result of differential activation of the aryl hydrocarbon receptor to interact with dioxin-responsive elements. Mol. Pharmacol. 2003, 63:915-924.