Tissue differences in the modulation of rat cytochromes P450 and phase II conjugation systems by dietary doses of phenethyl isothiocyanate

Food and Chemical Toxicology

Volumn 46, Issue 12, 2008, Pages 3677-3683

  Konsue, N ^a   Ioannides, C ^a  

^a UNIVERSITY OF SURREY   (United Kingdom)

Author keywords

Chemoprevention; Cytochromes P450; Isothiocyanates; Phenethyl isothiocyanate; Quinone reductase

Indexed keywords

CYTOCHROME P450; GLUTATHIONE TRANSFERASE; PHENETHYL ISOTHIOCYANATE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE (PHOSPHATE) DEHYDROGENASE (QUINONE);

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; CANCER PREVENTION; CHEMOPROPHYLAXIS; CONJUGATION; CONTROLLED STUDY; DETOXIFICATION; DIET SUPPLEMENTATION; DOSE RESPONSE; DRUG MECHANISM; DRUG MEGADOSE; ENZYME ACTIVITY; KIDNEY; LIVER; LOW DRUG DOSE; LUNG; MALE; NONHUMAN; RAT;

ANIMALS; CYTOCHROME P-450 ENZYME SYSTEM; DIET; DOSE-RESPONSE RELATIONSHIP, DRUG; ISOTHIOCYANATES; KIDNEY; LIVER; LUNG; MALE; MIXED FUNCTION OXYGENASES; RATS; RATS, WISTAR; WEIGHT GAIN; XENOBIOTICS;

RATTUS;

EID: 55949121573     PISSN: 02786915     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.fct.2008.09.046     Document Type: Article

References (54)

1. Akerboom T.P.H., and Sies H. Assay of glutathione, glutathione disulfide, and glutathione mixed disulfides in biological samples. Meth. Enzymol. 7 (1981) 373-382
2. Ambrosone C.B., McCann S.E., Freudenheim J.L., Marshall J.R., Zhang Y., and Shields P.G. Breast cancer risk in premenopausal women is inversely associated with consumption of broccoli, but is not modified by GST genotype. J. Nutr. 134 (2004) 1134-1138
3. Boysen G., Kenney P.M.J., Upadhaya P., Wang M., and Hecht S.S. Effects of benzyl isothiocyanate and 2-phenethyl isothiocyanate on benzo[a]pyrene and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone metabolism in F-344 rats. Carcinogenesis 24 (2003) 517-525
4. Bradford M.M. A rapid and sensitive method for the quantitation of microgram quantities of protein utilising the principle of protein-dye binding. Anal. Biochem. 72 (1976) 248-254
5. Burke M.D., and Mayer R.T. Ethoxyresorufin: direct fluorimetric assay of a microsomal O-dealkylation which is preferentially inducible by 3-methylcholanthrene. Drug Metab. Dispos. 2 (1974) 583-588
6. Burke M.D., and Mayer R.T. Differential effects of phenobarbitone and 3-methylcholanthrene induction on the hepatic microsomal and cytochrome P450 binding of phenoxazone and a homologous series of its n-alkyl ethers (alkoxyresorufins). Chem. Biol. Inter. 45 (1983) 243-258
7. Callberg I., and Mannervik B. Purification and characterisation of the flavoenzyme glutathione reductase from rat liver. J. Biol. Chem. 250 (1975) 5475-5480
8. Chung F.-L., Clifford Conaway C., Rao C.V., and Reddy B.S. Chemoprevention of aberrant crypt foci in Fischer rats by sulforaphane and phenethyl isothiocyanate. Carcinogenesis 21 (2000) 2287-2291
9. Chung F.-L. Chemoprevention of lung cancer by isothiocyanates and their conjugates in A/J mice. Exp. Lung Res. 27 (2001) 319-330
10. Conaway C.C., Wang C.-X., Pittman B., Yang Y.-M., Schwarz J.E., Tian D., McIntee E.J., Hecht S.S., and Chung F.-L. Phenethyl isothiocyanate and sulforaphane and their N-acetylcysteine conjugates inhibit malignant progression of lung adenomas induced by tobacco carcinogens in A/J mice. Cancer Res. 65 (2005) 8548-8557
11. Dingley K.H., Ubick E.A., Chiarappa-Zucca M.L., Nowell S., Abel S., Ebeler S.E., Mitchell A.E., Burns S.A., Steinberg F.M., and Clifford A.J. Effect of dietary constituents with chemopreventive potential on adduct formation of a low dose of the heterocyclic amines PhIP and IQ and phase II enzymes. Nutr. Cancer 46 (2003) 212-221
12. Guo Z., Smith T.J., Wang E., Sadrieh N., Ma Q., Thomas P.E., and Yang C.S. Effect of phenethyl isothiocyanate, a carcinogenesis inhibitor, on xenobiotic-metabolizing enzymes and nitrosamine metabolism in rats. Carcinogenesis 13 (1992) 2205-2210
13. Goosen T.C., Mills D.E., and Hollenberg P.F. Effects of benzyl iosthiocyanate on rat and human cytochromes P450: identification of metabolites formed by P450 2B1. J. Pharmacol. Exp. Ther. 296 (2001) 198-206
14. Habig W.H., Pabst M.J., and Jakoby W.B. Glutathione S-transferase, the first enzymic step in mercapturic acid formation. J. Biol. Chem. 249 (1974) 7130-7139
15. Hecht S.S. Inhibition of carcinogenesis by isothiocyanates. Drug Met. Rev. 32 (2000) 395-411
16. Hecht S.S., Trushin N., Rigotty J., Carmella S.G., Borukhova A., Akerkar S.A., and Rivenson A. Complete inhibition of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone induced rat lung tumorigenesis and favorable modification of biomarkers by phenethyl isothiocyanate. Cancer Epidem. Biomar. Prev. 5 (1996) 645-652
17. Herrero M.E., Arand M., Hengstler J.G., and Oesch F. Recombinant expression of human microsomal epoxide hydrolase protects V79 Chinese hamster cells from styrene oxide - but not from ethylene oxide-induced DNA strand breaks. Environ. Mol. Mutagen. 30 (1997) 429-439
18. Holst B., and Williamson G. A critical review of the bioavailability of glucosinolates and related compounds. Nat. Prod. Rep. 21 (2004) 425-447
19. Ishizaki H., Brady J.F., Ming S.M., and Yang C.S. Effect of phenethyl isothiocyanate on microsomal N-nitrosodimethylamine metabolism and other monooxygenase activities. Xenobiotica 20 (1990) 255-264
20. Jiao D., Yu M.C., Hankin J.H., Low S.-H., and Chung F.-L. Total isothiocyanate contents in cooked vegetables frequently consumed in Singapore. J. Agric. Food Chem. 46 (1998) 1055-1058
21. Kuroiwa Y., Nishikawa A., Kitamura Y., Kanki K., Ishii Y., Umemura T., and Hirose M. Protective effects of benzyl isothiocyanate and sulforaphane but not resveratrol against initiation of pancreatic carcinogenesis in hamsters. Cancer Lett. 241 (2006) 275-280
22. Lee M.-S. Enzyme induction and comparative oxidative desulfuration of isothiocyanates to isocyanates. Chem. Res. Toxicol. 9 (1996) 1072-1078
23. Lin H.J., Probst-Hensch N.M., Louie A., Kau I.H., Witte J.S., Ingles S.A., Frank H.D., Lee E.R., and Haile R.W. Glutathione transferase null genotype, broccoli, and lower prevalence of colorectal adenomas. Cancer Epidemiol. Biomar. Prev. 7 (1998) 647-652
24. London S.J., Yuan J.M., Chung F.L., Gao Y.T., Coetzee G.A., Ross R.K., and Yu M.C. Isothiocyanates, glutathione S-transferase M1 and T1 polymorphisms, and lung cancer risk: a prospective study in Shanghai, China. Lancet 356 (2000) 724-729
25. Lubet R.A., Mayer R.T., Cameron J.W., Nims R.N., Burke M.D., Wolf T., and Guengerich F. Dealkylation of pentoxyresorufin: a rapid and sensitive assay for measuring induction of cytochrome(s) P450 by phenobarbital and other xenobiotics in the rat. Arch. Biochem. Biophys. 238 (1985) 43-48
26. Manson M.M., Ball H.W.L., Barrett M.C., Clark H.L., Judah D.J., Williamson G., and Neal G.E. Mechanism of action of dietary chemopreventive agents in rat liver: induction of phase I and II drug metabolizing enzymes and aflatoxin B-1 metabolism. Carcinogenesis 18 (1997) 1729-1738
27. Maron M.D., and Ames B.N. Revised methods for the Salmonella mutagenicity test. Mut. Res. 113 (1983) 173-215
28. Moreno R.L., Goosen T., Kent U.M., Chung F.-L., and Hollenberg P.F. Differential effects of naturally occurring isothiocyanates on the activities of cytochrome P450 2E1 and the mutant P450 2E1 T303A. Arch. Biochem. Biophys. 391 (2001) 99-110
29. Morris C.R.I., Chen S.C., Zhou L., Schopfer L.M., Ding X., and Mirvish M.M. Inhibition by allyl sulfides and phenethyl isothiocyanate of methyl-n-pentylnitrosamine depentylation by rat esophageal microsomes, human and rat CYP2E1, and rat CYP2A3. Nutr. Cancer 48 (2004) 54-63
30. Morse M.A., Eklind K.I., Amin S.G., Hecht S.S., and Chung F.-L. Effects of alkyl chain length on the inhibition of NNK-induced neoplasia in A/J mice by arylalkyl isothiocyanates. Carcinogenesis 10 (1989) 1757-1759
31. Myzak M.C., Karplus P.A., Chung F.-Y., and Dashwood R.H. A novel mechanism of chemoprevention by sulforaphane: inhibition of histone deacetylase. Cancer Res. 64 (2004) 5767-5774
32. Nakajima M., Yoshida R., Shimada N., Yamazaki H., and Yokoi T. Inhibition and inactivation of human cytochrome P450 isoforms by phenethyl isothiocyanate. Drug Met. Disp. 29 (2001) 1110-1113
33. Nims R.W., and Lubet R.A. The CYP2B family. In: Ioannides C. (Ed). Cytochromes P450: Metabolic and Toxicological Aspects (1996), CRC Press Inc., Boca Raton 135-160
34. Nishikawa A., Furukawa F., Uneyama C., Ikezaki S., Tanakamaru Z., Chung F.-L., Takahashi M., and Hayashi Y. Chemopreventive effects of phenethyl isothiocyanate on lung pancreatic tumorigenesis in N-nitrosobis(2-oxopropyl)amine-treated hamsters. Carcinogenesis 17 (1996) 1381-1384
35. Plate A.Y.A., and Gallaher D.D. Effects of indole-3-carbinol and phenethyl isothiocyanate on colon carcinogenesis induced by azoxymethane in rats. Carcinogenesis 27 (2006) 287-292
36. Prohaska H.J., and Santamaria A.B. Direct measurement of NAD(P)H: quinone reductase from cells cultured in microtiter wells: a screening assay for anticarcinogenic enzyme inducers. Anal. Biochem. 169 (1988) 328-336
37. Reinke L.A., and Moyer M.J. P-Nitrophenol hydroxylation: a microsomal oxidation which is highly inducible by ethanol. Drug Met. Disp. 13 (1985) 548-552
38. Ricci G., Caccuri A., Bello M., Pastore A., Piemonte F., and Federici G. Colorimetric and fluorometric assays of glutathione-S-transferase based on 7-chloro-4-nitrobenzo-2-oxa-1,3-diazole. Anal. Biochem. 218 (1994) 463-465
39. Sherratt P.J., and Hayes J.D. Glutathione S-transferases. In: Ioannides C. (Ed). Enzyme Systems that Metabolise Drugs and other Xenobiotics (2002), John Wiley & Sons, Ltd., Chichester 319-352
40. Smith T.J., Guo Z.Y., Li C., Ning S.M., Thomas P.E., and Yang C.S. Mechanisms of inhibition of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone bioactivation in mouse by dietary phenethyl isothiocyanate. Cancer Res. 53 (1993) 3276-3282
41. Staretz M.E., and Hecht SS. Effects of phenethyl isothiocyanate on the tissue distribution of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone and metabolites in F-344 rats. Cancer Res. 55 (1995) 5580-5588
42. Stoner G.D., Morissey D., Heu Y.-H., Daniel E.M., Galati A.J., and Wagner S.A. Inhibitory effects of phenethyl isothiocyanate on N-nitrosobenzylmethylamine carcinogenesis in the rat esophagus. Cancer Res. 51 (1991) 2063-2068
43. Stresser D.M., Turner S.D., Blanchard A.P., Miller V.P., and Crespi C.L. Cytochrome P450 fluorimetric substrates: identification of isoform-selective probes for rat CYP2D2 and human CYP3A4. Drug Met. Disp. 30 (2002) 845-852
44. Takagi H., Shibutani M., Uneyama C., Lee K.-Y., Kato N., Inoue K., and Hirose M. Limited tumor-initiating activity of phenylethyl isothiocyanate by promotion with sodium l-ascorbate in rat two-stage urinary bladder carcinogenesis model. Cancer Lett. 219 (2005) 147-153
45. Talalay P., and Fahey J.W. Phytochemicals from cruciferous plants protect against cancer by modulating carcinogen metabolism. J. Nutr. 131 (2001) 3027S-3033S
46. Turesky J. Heterocyclic aromatic amine metabolism, DNA adduct formation, mutagenesis and carcinogenesis. Drug Met. Rev. 34 (2002) 625-650
47. Verhoeven D.T.H., Goldbohm R.A., van Poppel G., Verhagen H., and van den Brandt P.A. Epidemiological studies on Brassica vegetables and cancer risk. Cancer Epidemiol. Biomar. Prev. 5 (1996) 733-748
48. Von Weymarn L.B., Chun J.A., and Hollenberg P.F. Effects of benzyl and phenethyl isothiocyanate on P450 2A6 and 2A13: potential for chemoprevention in smokers. Carcinogenesis 27 (2006) 782-790
49. Von Weymarn L.B., Chun J.A., Knudsen G.A., and Hollenberg P.F. Effects of eleven isothiocyanates on P450 2A6 - and 2A13-catalyzed coumarin 7-hydroxylation. Chem. Res. Toxicol. 20 (2007) 1952-1959
50. Wattenberg L.W. Inhibition of carcinogenic effects of polycyclic aromatic hydrocarbons by benzyl isothiocyanate and related compounds. J. Natl. Cancer Inst. 58 (1977) 395-398
51. Xu K., and Thornalley P.J. Involvement of glutathione metabolism in the cytotoxicity of the phenethyl isothiocyanate and its cysteine conjugate to human leukaemia cells in vitro. Biochem. Pharmacol. 61 (2001) 165-177
52. Yoxall V., Kentish P., Coldham N., Kuhnert N., Sauer M.J., and 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 117 (2005) 356-362
53. Zhang Y. Cancer-preventive isothiocyanates: measurement of human exposure and mechanism of action. Mut. Res. 555 (2004) 173-190
54. Zhao Y., Yao S., and Li J. Vegetable-derived isothiocyanates: anti-proliferative activity and mechanism of action. Proc. Nutr. Soc. 65 (2006) 68-75