Effects of benzyl-, phenethyl-, and α-naphthyl isothiocyanates on P-glycoprotein- and MRP1-mediated transport

Journal of Pharmaceutical Sciences

Volumn 93, Issue 7, 2004, Pages 1901-1911

  Hu, Ke ^a   Morris, Marilyn E ^a  

^a UNIVERSITY AT BUFFALO   (United States)

Author keywords

Benzyl isothiocyanate; Daunomycin; MRP1; Multidrug resistance; Naphthyl isothiocyanate; P glycoprotein; Phenethyl isothiocyanate

Indexed keywords

1 NAPHTHYL ISOTHIOCYANATE; AMINE; BENZYL ISOTHIOCYANATE; DAUNORUBICIN; GLUTATHIONE TRANSFERASE; GLYCOPROTEIN P; ISOTHIOCYANIC ACID DERIVATIVE; MULTIDRUG RESISTANCE PROTEIN 1; PHENETHYL ISOTHIOCYANATE; VERAPAMIL; VERLUKAST;

ARTICLE; COLON ADENOCARCINOMA; CONTROLLED STUDY; DRUG DETERMINATION; DRUG MECHANISM; DRUG PROTEIN BINDING; ENZYME SUBSTRATE; EVALUATION; GENE OVEREXPRESSION; HUMAN; HUMAN CELL; MULTIDRUG RESISTANCE;

EID: 3042552897     PISSN: 00223549     EISSN: None     Source Type: Journal    
DOI: 10.1002/jps.20101     Document Type: Article

References (39)

1. Juliano RL, Ling V. 1976. A surface glycoprotein modulating drug permeability in Chinese hamster ovary cell mutants. Biochim Biophys Acta 455:152-162.
2. Cole SP, Bhardwaj G, Gerlach JH, Mackie JE, Grant CE, Almquist KC, Stewart AJ, Kurz EU, Duncan AM, Deeley RG. 1992. Overexpression of a transporter gene in a multidrug-resistant human lung cancer cell line. Science 258:1650-1654.
3. Zhang Y, Talalay P. 1994. Anticarcinogenic activities of organic isothiocyanates: Chemistry and mechanisms. Cancer Res 54(Suppl 7):1976s-1981s.
4. Hecht SS. 2000. Inhibition of carcinogenesis by isothiocyanates. Drug Metab Rev 32:395-411.
5. Zhang Y, Talalay P. 1998. Mechanism of differential potencies of isothiocyanates as inducers of anticarcinogenic Phase 2 enzymes. Cancer Res 58:4632-4639.
6. Hu R, Kim BR, Chen C, Hebbar V, Kong AN. 2003. The roles of JNK and apoptotic signaling pathways in PEITC-mediated responses in human HT-29 colon adenocarcinoma cells. Carcinogenesis 24:1361-1367.
7. Tseng E, Kamath A, Morris ME. 2002. Effect of organic isothiocyanates on the P-glycoprotein- and MRP1-mediated transport of daunomycin and vinblastine. Pharm Res 19:1509-1515.
8. Conaway CC, Jiao D, Kohri T, Liebes L, Chung FL. 1999. Disposition and pharmacokinetics of phenethyl isothiocyanate and 6-phenylhexyl isothiocyanate in F344 rats. Drug Metab Dispos 27:13-20.
9. Xu K, Thornalley PJ. 1999. Synthesis of C-14-labelled phenethyl isothiocyanate and the cysteine conjugate S-(N-phenethylthiocarbamoyl) cysteine and use under physiological conditions. J Radiolabelled Cpd Radiopharm 42:1069-1074.
10. Zhang S, Morris ME. 2003. Effect of the flavonoids biochanin A and silymarin on the P-glycoprotein-mediated transport of digoxin and vinblastine in human intestinal Caco-2 cells. Pharm Res 20:1184-1191.
11. Tietze F. 1969. Enzymic method for quantitative determination of nanogram amounts of total and oxidized glutathione: Applications to mammalian blood and other tissues. Anal Biochem 27:502-522.
12. Habig WH, Pabst MJ, Jakoby WB. 1974. Glutathione S-transferases. The first enzymatic step in mercapturic acid formation. J Biol Chem 249:7130-7139.
13. Hu K, Morris ME. 2003. Determination of alpha-naphthylisothiocyanate and metabolites alpha-naphthylamine and alpha-naphthylisocyanate in rat plasma and urine by high-performance liquid chromatography. J Chromatogr B Anal Technol Biomed Life Sci 788:17-28.
14. Zhang S, Morris ME. 2003. Effects of the flavonoids biochanin A, morin, phloretin, and silymarin on P-glycoprotein-mediated transport. J Pharmacol Exp Ther 304:1258-1267.
15. Nguyen H, Zhang S, Morris ME. 2003. Effect of flavonoids on MRPl-mediated transport in Panc-1 cells. J Pharm Sci 92:250-257.
16. Lee MS. 1996. Enzyme induction and comparative oxidative desulfuration of isothiocyanates to isocyanates. Chem Res Toxicol 9:1072-1078.
17. Xu K, Thornalley PJ. 2000. Studies on the mechanism of the inhibition of human leukaemia cell growth by dietary isothiocyanates and their cysteine adducts in vitro. Biochem Pharmacol 60:221-231.
18. Goosen TC, Mills DE, Hollenberg PF. 2001. Effects of benzyl isothiocyanate on rat and human cytochromes P450: Identification of metabolites formed by P450 2B1. J Pharmacol Exp Ther 296:198-206.
19. Zhang Y, Callaway EC. 2002. High cellular accumulation of sulphoraphane, a dietary anticarcinogen, is followed by rapid transporter-mediated export as a glutathione conjugate. Biochem J 364(Pt 1):301-307.
20. Breier A, Ziegelhoffer A, Famulsky K, Michalak M, Slezak J. 1996. Is cysteine residue important in FITC-sensitive ATP-binding site of P-type ATPases? A commentary to the state of the art. Mol Cell Biochem 160-161:89-93.
21. Dinkova-Kostova AT, Massiah MA, Bozak RE, Hicks RJ, Talalay P. 2001. Potency of Michael reaction acceptors as inducers of enzymes that protect against carcinogenesis depends on their reactivity with sulfhydryl groups. Proc Natl Acad Sci USA 98:3404-3409.
22. al-Shawi MK, Urbatsch IL, Senior AE. 1994. Covalent inhibitors of P-glycoprotein ATPase activity. J Biol Chem 269:8986-8992.
23. Adesida A, Edwards LG, Thornalley PJ. 1996. Inhibition of human leukaemia 60 cell growth by mercapturic acid metabolites of phenylethyl isothiocyanate. Food Chem Toxicol 34:385-392.
24. Zhang Y. 2000. Role of glutathione in the accumulation of anticarcinogenic isothiocyanates and their glutathione conjugates by murine hepatoma cells. Carcinogenesis 21:1175-1182.
25. Jedlitschky G, Leier I, Buchholz U, Barnouin K, Kurz G, Keppler D. 1996. Transport of glutathione, glucuronate, and sulfate conjugates by the MRP gene-encoded conjugate export pump. Cancer Res 56:988-994.
26. Zaman GJ, Lankelma J, van Tellingen O, Beijnen J, Dekker H, Paulusma C, Oude Elferink RP, Baas F, Borst P. 1995. Role of glutathione in the export of compounds from cells by the multidrug-resistance-associated protein. Proc Natl Acad Sci USA 92:7690-7694.
27. Salerno M, Garnier-Suillerot A. 2001. Kinetics of glutathione and daunorubicin efflux from multidrug resistance protein overexpressing small-cell lung cancer cells. Eur J Pharmacol 421:1-9.
28. Leslie EM, Deeley RG, Cole SP. 2003. Bioflavonoid stimulation of glutathione transport by the 190-kDa multidrug resistance protein 1 (MRP1). Drug Metab Dispos 31:11-15.
29. Thornalley PJ. 2002. Isothiocyanates: Mechanism of cancer chemopreventive action. Anticancer Drugs 13:331-338.
30. Zhang Y. 2001. Molecular mechanism of rapid cellular accumulation of anticarcinogenic isothiocyanates. Carcinogenesis 22:425-431.
31. Zhang Y, Kolm RH, Mannervik B, Talalay P. 1995. Reversible conjugation of isothiocyanates with glutathione catalyzed by human glutathione transferases. Biochem Biophys Res Commun 206:748-755.
32. Conaway CC, Krzeminski J, Amin S, Chung FL. 2001. Decomposition rates of isothiocyanate conjugates determine their activity as inhibitors of cytochrome p450 enzymes. Chem Res Toxicol 14:1170-1176.
33. Xu K, Thornalley PJ. 2001. Involvement of glutathione metabolism in the cytotoxicity of the phenethyl isothiocyanate and its cysteine conjugate to human leukaemia cells in vitro. Biochem Pharmacol 61:165-177.
34. Carpenter-Deyo L, Marchand DH, Jean PA, Roth RA, Reed DJ. 1991. Involvement of glutathione in 1-naphthylisothiocyanate (ANIT) metabolism and toxicity to isolated hepatocytes. Biochem Pharmacol 42:2171-2180.
35. Li Y, Yousef IM, Plaa GL. 1995. 1-Naphthyl isocyanate and 1-naphthylamine as metabolites of 1-naphthylisothiocyanate. Liver 15:271-275.
36. Mehendale HM, Roth RA, Gandolfi AJ, Klaunig JE, Lemasters JJ, Curtis LR. 1994. Novel mechanisms in chemically induced hepatotoxicity. FASEB J 8:1285-1295.
37. Roth RA, Dahm LJ. 1997. Neutrophil- and glutathione-mediated hepatotoxicity of alpha- naphthylisothiocyanate. Drug Metab Rev 29:153-165.
38. Dietrich CG, Ottenhoff R, de Waart DR, Oude Elferink RP. 2001. Role of MRP2 and GSH in intrahepatic cycling of toxins. Toxicology 167:73-81.
39. Jiang ZQ, Chen C, Yang B, Hebbar V, Kong AN. 2003. Differential responses from seven mammalian cell lines to the treatments of detoxifying enzyme inducers. Life Sci 72:2243-2253.