Sulforaphane and its analogues inhibit CYP1A1 and CYP1A2 activity induced by benzo[a]pyrene

Journal of Biochemical and Molecular Toxicology

Volumn 23, Issue 1, 2009, Pages 18-28

  Skupinska, Katarzyna ^a   Misiewicz Krzeminska, Irena ^a   Stypulkowski, Rafal ^a   Lubelska, Katarzyna ^a   Kasprzycka Guttman, Teresa ^a  

^a NATIONAL MEDICINES INSTITUTE   (Poland)

Author keywords

Chemoprevention; CYP1A1; CYP1A2; Isothiocyanates; Polycyclic aromatic hydrocarbons

Indexed keywords

ALYSSIN; AROMATIC HYDROCARBON RECEPTOR; BENZO[A]PYRENE; CYTOCHROME P450 1A1; CYTOCHROME P450 1A2; ISOTHIOCYANATE 2 OXOHEXYL; ISOTHIOCYANIC ACID; SULFORAPHANE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMOPROPHYLAXIS; DRUG ACTIVITY; ENZYME INHIBITION; HUMAN; HUMAN CELL;

BENZO(A)PYRENE; CELL LINE, TUMOR; CELL NUCLEUS; CYTOCHROME P-450 CYP1A1; CYTOCHROME P-450 CYP1A2; ENZYME INDUCTION; HUMANS; PROTEIN TRANSPORT; RECEPTORS, ARYL HYDROCARBON; THIOCYANATES;

BRASSICA;

EID: 59949104984     PISSN: 10956670     EISSN: 10990461     Source Type: Journal    
DOI: 10.1002/jbt.20259     Document Type: Article

References (37)

1. Jongeneelen FJ, van Leeuwen FE, Oosterink S, Anzion RB, van der Loop F, Bos RP, van Veen HG. Ambient and biological monitoring of cokeoven workers: Determinants of the internal dose of polycyclic aromatic hydrocarbons. Br J Ind Med 1990;47:454-461.
2. Zhang KL, Ma JX, Chen XY, Sun Y, Kong QY, Liu J, Li H. Frequent CYP1A1 expression in gastric cancers and their related lesions. Oncol Rep 2004;12:1335-1340.
3. 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.
4. Coumoul X, Diry M, Robillot C, Barouki R. Differential regulation of cytochrome P450 1A1 and 1B1 by a combination of dioxin and pesticides in the breast tumor cell line MCF-7. Cancer Res 2001;61:3942-3948.
5. Shimada T, Inoune K, Suzuki Y, Kawai T, Azuma E, Nakajima T, Shindo M, Kurose K, Sugie A, Yamagishi Y, Fujii-Kuriyama Y, Hashimoto M. Arylhydrocarbon receptor-dependent induction of liver and lung cytochromes P450 1A1, 1A2 and 1B1 by polycyclic aromatic hydrocarbons and polychlorinated biphenyls in genetically engineered C57BL/6J mice. Carcinogenesis 2002;23:1199-1207.
6. Arin c E, Sen A, Bozcaarmutlu A. Cytochrome P4501A and associated mixed function oxidase induction in fish as biomarker for toxic carcinogenic pollutants the aquatic environment. Pure Appl Chem 2000;72:985-994.
7. Skupinska K, Misiewicz I, Kasprzycka-Guttman T. A comparison of the concentration-effect relationships of PAHs on CYP1A induction in HepG2 and Mcf7 cells. Arch Toxicol 2007;81:183-200.
8. Decaprio AP. Biomarkers: Coming of age for environmental health and risk assessment. Environ Sci Technol 1997;31:1837-1848.
9. 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;16:415-422.
10. Nishikawa A, Furukawa F, Uneyama C, Ikezaki S, Tanakamaru Z, Chung FL, Takahashi M, Hayashi Y. Chemopreventive effects of phenethyl isothiocyanate on lung and pancreatic tumorigenesis in N-nitrosobis(2-oxopropyl)amine-treated hamsters. Carcinogenesis 1996;17:1381-1384.
11. Hecht SS, Kenney PM, 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.
12. Conaway CC, Jiao D, Chung FL. Inhibition of rat liver cytochrome P450 isozymes by isothiocyanates and their conjugates: A structure-activity relationship study. Carcinogenesis 1996;17:2423-2427.
13. Mahéo K, Morel F, Langouët S, Kramer H, Le Ferrec E, Ketterer B, Guillouzo A. Inhibition of cytochromes P-450 and induction of glutathione S-transferases by sulforaphane in primary human and rat hepatocytes. Cancer Res 1997;57:3649-3652.
14. Conaway CC, Yang YM, Chung FL. Isothiocyanates as cancer chemopreventive agents: Their biological activities and metabolism in rodents and humans. Curr Drug Metab 2002;3:233-255.
15. Schmid H, Karrer P. Synthese der racemischen und der optisch aktiven Formen des sulforaphans. Helv Chem Acta 1948;31:1497-1505.
16. MacDonald CJ, Ciolino HP, Yeh GC. The drug salicylamide is an antagonist of the aryl hydrocarbon receptor that inhibits signal transduction induced by 2,3,7,8-tetrachlorodibenzo-p-dioxin. Cancer Res 2004;64:429-434.
17. Ciolino HP, MacDonald CJ, Yeh GC. Inhibition of carcinogen-activating enzymes by 16α-fluoro-5-androsten-17-one. Cancer Res 2002;62:3685-3690.
18. Burke MD, Thompson S, Elcombre CR, Halpert J, Haaparanta T, Mayer RT. Ethoxy-, pentoxy- and benzyloxyphenoxazones and homologues: A series of substrates to distinguish between different induced cytochromes P-450. Biochem Pharmacol 1985;34:3337-3345.
19. Bradford MM. A rapid sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem 1976;72:248-254.
20. Loaiza-Pérez AI, Trapani V, Hose C, Singh SS, Trepel JB, Stevens MF, Bradshaw TD, Sausville EA. Aryl hydrocarbon receptor mediates sensitivity of MCF-7 breast cancer cells to antitumor agent 2-(4-amino-3-methylphenyl) benzothiazole. Mol Pharmacol 2002;61:13-19.
21. Bosetti C, Boffetta P, La Vecchia C. Occupational exposures to polycyclic aromatic hydrocarbons, and respiratory and urinary tract cancers: A quantitative review to 2005. Ann Oncol 2007;18:431-446.
22. Juge N, Mithen RF, Traka M. Molecular basis for chemo-prevention by sulforaphane: A comprehensive review. Cell Mol Life Sci 2007;64:1105-1127.
23. Misiewicz I, Skupinska K, Kasprzycka-Guttman T. Sulforaphane and 2-oxohexyl isothiocyanate induce cell growth arrest and apoptosis in L-1210 leukemia and ME- 18 melanoma cells. Oncol Rep 2003;10:2045-2050.
24. Misiewicz I, Skupinska K, Kasprzycka-Guttman T. Sulforaphane-mediated induction of a phase 2 detoxifying enzyme NAD(P)H:quinone reductase and apoptosis in human lymphoblastoid cells. Acta Biochim Pol 2004;51:711-721.
25. Zhang Y, Talalay P, Cho CG, Posner GH. A major inducer of anticarcinogenic protective enzymes from broccoli: Isolation and elucidation of structure. Proc Natl Acad Sci USA 1992;89:2399-2403.
26. Sparfel L, Huc L, Le Vee M, Desille M, Lagadic-Gossmann D, Fardel O. Inhibition of carcinogen-bioactivating cytochrome P450 1 isoforms by amiloride derivatives. Biochem Pharmacol 2004;67:1711-1719.
27. Jørgensen ECB, Autrup H. Autoregulation of human CYP1A1 gene promoter activity in HepG2 and MCF-7 cells. Carcinogenesis 1996;17:435-441.
28. Bacon JR, Williamson G, Garner RC, Lappin G, Langouet S, Bao Y. Sulforaphane and quercetin modulate PhIP-DNA adduct formation in human HepG2 cells and hep-atocytes. Carcinogenesis 2003;24:1903-1911.
29. Hanlon PR, Webber DM, Barnes DM. Aqueous extract from Spanish black radish (Raphanus sativus L. var. niger) induces detoxification enzymes in the HepG2 human hepatoma cell line. J Agric Food Chem 2007;55:6439-6446.
30. Yoxall V, Kentish P, Coldham N, Kuhnert N, Sauer MJ, Ioannides C. Modulation of hepatic cytochromes P450 and phase II enzymes by dietary doses of sulforaphane in rats: Implications for its chemopreventive activity. Int J Cancer 2005;117:356-362.
31. Langouët S, Furge LL, Kerriguy N, Nakamura K, Guillouzo A, Guengerich FP. Inhibition of human cytochrome P450 enzymesby1,2-dithiole-3- thione,oltipraz and its derivatives, and sulforaphane. Chem Res Toxicol 2000;13:245-252.
32. Chang TKH, Chen J, Lee WBK. Differential inhibition and inactivation of human CYP1 enzymes by trans-resveratrol: Evidence for mechanism-based inactivation of CYP1A2. J Pharmacol Exp Ther 2001;299: 874-882.
33. Wen X, Walle UK, Walle T. 5,7-Dimethoxyflavone downregulates CYP1A1 expression and benzo[a]pyrene- induced DNA binding in Hep G2 cells. Carcinogenesis 2005;26:803-809.
34. Han W, Pentecost BT, Pietropaolo RL, Fasco MJ, Spivack SD. Estrogen receptor alpha increases basal and cigarette smoke extract-induced expression of CYP1A1 and CYP1B1, but not GSTP1, in normal human bronchial epithelial cells. Mol Carcinog 2005;44:202-211.
35. Matthews J, Wihlén B, Thomsen J, Gustafsson JA. Aryl hydrocarbon receptor-mediated transcription: Ligand-dependent recruitment of estrogen receptor alpha to 2,3,7,8-tetrachlorodibenzo-p-dioxin-responsive promoters. Mol Cell Biol 2005;25:5317-5328.
36. Pledgie-Tracy A, Sobolewski MD, Davidson NE. Sulforaphane induces cell type-specific apoptosis in human breast cancer cell lines. Mol Cancer Ther 2007;6:1013-1021.
37. Erkoç, Erkoç F. Theoretical investigation of sulforaphane molecule. J Mol Struct 2005;714:81-85.