Modulation of rat pulmonary carcinogen-metabolising enzyme systems by the isothiocyanates erucin and sulforaphane

Chemico-Biological Interactions

Volumn 177, Issue 2, 2009, Pages 115-120

  Hanlon, Natalya ^a   Coldham, Nick ^b   Sauer, Maurice J ^b   Ioannides, Costas ^a  

^a UNIVERSITY OF SURREY   (United Kingdom)

^b VETERINARY LABORATORIES AGENCY   (United Kingdom)

Author keywords

Chemoprevention; CYP1; Erucin; Isothiocyanates; Quinone reductase; Sulforaphane

Indexed keywords

1 CHLORO 2,4 DINITROBENZENE; 3 (4,5 DIMETHYL 2 THIAZOLYL) 2,5 DIPHENYLTETRAZOLIUM BROMIDE; CARCINOGEN; CYTOCHROME P450 1A1; CYTOCHROME P450 1B1; CYTOCHROME P450 2B; CYTOCHROME P450 3A2; ERUCIN; ETHOXYRESORUFIN; GLUTATHIONE TRANSFERASE; GLUTATHIONE TRANSFERASE ALPHA; GLUTATHIONE TRANSFERASE P1; LACTATE DEHYDROGENASE; PENTOXYRESORUFIN; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE (PHOSPHATE) DEHYDROGENASE (QUINONE); SULFORAPHANE;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; CHEMICAL REACTION; CHEMOPROPHYLAXIS; CONCENTRATION RESPONSE; CONTROLLED STUDY; CYTOSOL; DRUG EFFECT; ENZYME ACTIVITY; ENZYME SUBSTRATE COMPLEX; LUNG CARCINOGENESIS; LUNG SLICE; MALE; NONHUMAN; PROTEIN BLOOD LEVEL; RAT; UPREGULATION; WISTAR RAT;

ANIMALS; ANTICARCINOGENIC AGENTS; ARYL HYDROCARBON HYDROXYLASES; CYTOSOL; DOSE-RESPONSE RELATIONSHIP, DRUG; GLUTATHIONE; LUNG; MALE; ORGAN CULTURE TECHNIQUES; OXAZINES; RATS; RATS, WISTAR; SULFIDES; THIOCYANATES; UP-REGULATION;

RATTUS;

EID: 57649184041     PISSN: 00092797     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cbi.2008.08.015     Document Type: Article

References (42)

1. Stan S.D., Kar S., Stoner G.D., and Singh S.V. Bioactive food components and cancer risk reduction. J. Cell Biochem. 104 (2008) 339-356
2. Zhang Y., Talalay P., Cho G.C., and Posner G.H. A major inducer of anticarcinogenic protective enzymes from broccoli: isolation and elucidation of structure. Proc. Natl. Acad. Sci. 89 (1992) 2399-2403
3. Getahun S.M., and Chung F.L. Conversion of isothiocyanates in humans after ingestion of cooked watercress. Cancer Epidemiol. Biomark. Prev. 8 (1999) 447-451
4. Zhao H., Grossman H.B., Hernandez L.M., Dinney C.P., and Wu X. Dietary isothiocyanates, GSTM1, GSTT1, NAT2 polymorphisms and bladder cancer risk. Int. J. Cancer 120 (2007) 2208-2213
5. Spitz M.R., Duphorne C.M., Detry M.A., Pillow P.C., Amos C.I., Lei L., de Andrade M., Gu X.J., Hong W.K., and Wu X.F. Dietary intake of isothiocyanates: evidence of a joint effect with glutathione S-transferase polymorphisms in lung cancer risk. Cancer Epidemiol. Biomark. Prev. 9 (2000) 1017-1020
6. Hecht S.S., Kenney P.M., Wang M., Trushin N., and Upadhyaya P. 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. 13 (2000) 49-56
7. Hecht S.S., Kenney P.M., Wang M., Trushin N., and Upadhyaya P. Benzyl isothiocyanate: an effective inhibitor of polycyclic aromatic hydrocarbon tumorigenesis in A/J mouse lung. Cancer Lett. 187 (2002) 87-94
8. Wattenberg L.W. Inhibitory effects of benzyl isothiocyanate administered shortly before diethylnitrosamine or benzo[a]pyrene on pulmonary and forestomach neoplasia in A/J mice. Carcinogenesis 8 (1987) 1971-1973
9. Morse M.A., Wang C.X., Stoner G.D., Mandal S., Conran P.G., Amin S.G., Hecht S.S., and Chung F.L. Inhibition of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone-induced DNA adduct formation and tumorigenicity in the lung of F344 rats by dietary phenethyl isothiocyanates. Cancer Res. 49 (1989) 549-553
10. Conaway C.C., Wang C.-X., Pittman B., Yang Y.-M., Schwartz 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 (2005) 8548-8557
11. Conaway C.C., Yang Y.-M., and Chung F.-L. Isothiocyanates as cancer chemopreventive agents: their biological activities and metabolism in rodents and humans. Curr. Drug Metab. 3 (2002) 233-255
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. N. Konsue, C. Ioannides, Tissue differences in the modulation of rat cytochromes P450 and phase II conjugation systems by dietary doses of phenethyl isothiocyanate, Food Chem. Toxicol., in press.
14. N. Hanlon, N. Coldham, M.J. Sauer, C. Ioannides, Up-regulation of the CYP1 family in rat and human liver by the aliphatic isothiocyanates erucin and sulforaphane, Toxicology, in press.
15. Umachandran M., Howarth J., and Ioannides C. Metabolic and structural viability of precision-cut rat lung slices in culture. Xenobiotica 34 (2004) 771-780
16. Lerche-Langrand C., and Toutain H.J. Precision-cut liver slices: characteristics and use for in vitro pharmaco-toxicology. Toxicology 153 (2000) 221-253
17. Hukkanen J., Pelkonen O., Hakkola J., and Raunio H. Expression and regulation of xenobiotic-metabolizing cytochrome P450 (CYP) enzymes in human lung. Crit. Rev. Toxicol. 32 (2002) 391-411
18. Pushparajah D.S., Umachandran M., Plant K.E., Plant N., and Ioannides C. Evaluation of the precision-cut liver and lung slice systems for the study of induction of CYP1, epoxide hydrolase and glutathione S-transferase activities. Toxicology 231 (2007) 68-80
19. Lake B.G., Beamand J.A., Japenga A.C., Renwick A., Davies S., and Price R.J. Induction of cytochrome P-450-dependent enzyme activities in cultured rat slices. Food Chem. Toxicol. 31 (1993) 377-386
20. 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
21. Lubet R.A., Mayer R.T., Cameron J.W., Nims R.N., Burke M.D., Wolf T., and Guengerich F.P. 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
22. 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
23. 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
24. Akerboom T.P.H., and Sies H. Assay of glutathione, glutathione disulfide, and glutathione mixed disulfides in biological samples. Methods Enzymol. 7 (1981) 373-382
25. 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
26. Schwartz A.G., Prysak G.M., Bock C.H., and Cote M.L. The molecular epidemiology of cancer. Carcinogenesis 28 (2007) 507-518
27. Ioannides C., and Lewis D.F.V. Cytochromes P450 in the bioactivation of chemicals. Curr. Topics Med. Chem. 4 (2004) 1767-1788
28. Wall K.L., Gao W., TeKoppele J.M., Kwei G.Y., Kauffman F.C., and Thurman R.G. The liver plays a central role in the mechanism of chemical carcinogenesis due to polycyclic aromatic hydrocarbons. Carcinogenesis 12 (1991) 783-786
29. Kaderlik K.R., Minchin R.F., Mulder G.J., Ilett K.F., Daugaard-Jenson M., Teitel C.H., and Kadlubar F.F. Metabolic activation pathway for the formation of DNA adducts of the carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in rat extrahepatic tissues. Carcinogenesis 15 (1994) 1703-1709
30. Alexandrov K., Rojas M., Geneste O., Castegnaro M., Camus A.-M., Petruzzelli S., Giuntini C., and Bartsch H. An improved fluorometric assay for dosimetry of benzo(a)pyrene diol-epoxide-DNA adducts in smokers' lung-comparisons with total bulky adducts and aryl-hydrocarbon hydroxylase-activity. Cancer Res. 52 (1992) 6248-6253
31. Bartsch H., Castegnaro M., Rojas M., Camus A.-M., Alexandrov K., and Lang M. Expression of pulmonary cytochrome P4501A1 and carcinogen adduct formation in high risk subjects for tobacco-related lung cancer. Toxicol. Lett. 64/65 (1992) 477-483
32. Anttila S., Vainio H., Hietanen H., Camus A.-M., Malaveille C., Brun G., Husgafvel-Pursiainen K., Heikkila L., Karjalainen A., and Bartsch H. Immunohistochemical detection of pulmonary cytochrome P450IA and metabolic activities associated with P450IA1 and P450IA2 isozymes in lung cancer patients. Environ. Health Perspect. 98 (1992) 179-182
33. N. Hanlon, A. Okpara, N. Coldham, M.J. Sauer, C. Ioannides, Modulation of rat hepatic and pulmonary cytochromes P450 and phase II enzyme systems by erucin, an isothiocyanate structurally related to sulforaphane, J. Agric. Food Chem., in press.
34. Lee M.-S. Enzyme induction and comparative oxidative desulfuration of isothiocyanates to isocyanates. Chem. Res. Toxicol. 9 (1996) 1072-1078
35. Bolt H.M., and Roos P.H. In: Ioannides C. (Ed). Cytochromes P450: Role in the Metabolism and Toxicity of Drugs and Other Xenobiotics (2008), RSC Publishing, Cambridge 46-94
36. N. Hanlon, C.L. Poynton, N. Coldham, M.J. Sauer, C. Ioannides, The aliphatic isothiocyanates erucin and sulforaphane do not effectively up-regulate quinone reductase in human liver compared with rat, submitted for publication, Molec. Nutr. Food Res., in press.
37. 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
38. Hanlon N., Coldham N., Gielbert A., Kuhnert N., Sauer M.J., King L.J., and Ioannides C. Absolute bioavailability and dose-dependent pharmacokinetic behaviour of dietary doses of the chemopreventive isothiocyanate sulforaphane in the rat. Br. J. Nutr. 99 (2008) 559-564
39. Al Janobi A.A., Mithen R.F., Gasper A.V., Shaw P.N., Middleton R.J., Ortori C.A., and Barrett D.A. Quantitative measurement of sulforaphane, iberin and their mercapturic acid pathway metabolites in human plasma and urine using liquid chromatography-tandem electrospray ionisation mass spectrometry. J. Chromatogr. B 844 (2006) 223-234
40. Seow A., Vainio H., and Yu M.C. Effect of glutathione-S-transferase polymorphisms on the cancer preventive potential of isothiocyanates: an epidemiological perspective. Mutat. Res. 592 (2005) 58-67
41. Bheemreddy R.M., and Jeffery E.H. The metabolic fate of purified glucoraphanin in F344 rats. J. Agric. Food Chem. 55 (2007) 2861-2866
42. Kassahun K., Davis M., Hu P., Martin B., and Baillie T. Biotransformation of the naturally occurring isothiocyanate sulforaphane in the rat: identification of phase I metabolites and glutathione conjugates. Chem. Res. Toxicol. 10 (1997) 1228-1233