Modulation of human Multidrug Resistance Protein (MRP) 1 (ABCC1) and MRP2 (ABCC2) transport activities by endogenous and exogenous glutathione-conjugated catechol metabolites

Drug Metabolism and Disposition

Volumn 36, Issue 3, 2008, Pages 552-560

  Slot, Andrew J ^a   Wise, Dana D ^b   Deeley, Roger G ^a   Monks, Terrence J ^b   Cole, Susan P C ^a,c  

^a QUEEN S UNIVERSITY   (Canada)

^b UNIVERSITY OF ARIZONA   (United States)

^c QUEEN S UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

17BETA ESTRADIOL 17 (BETA DEXTRO GLUCURONIDE); 2 (GLUTATHION S YL) CAFFEIC ACID; 2 HYDROXY 1 (GLUTATHION S YL) ESTRADIOL; 2 HYDROXY 1 (GLUTATHION S YL) ESTRONE; 5 (GLUTATHION S YL) N METHYL ALPHA METHYLDOPAMINE; ACETYLCYSTEINE; ADENOSINE TRIPHOSPHATE; CAFFEIC ACID; CATECHOL; DOPAMINE DERIVATIVE; DRUG METABOLITE; ESTRADIOL DERIVATIVE; ESTROGEN DERIVATIVE; ESTRONE DERIVATIVE; GLUCURONIDE; GLUTATHIONE; LEUKOTRIENE C4; MULTIDRUG RESISTANCE PROTEIN 1; MULTIDRUG RESISTANCE PROTEIN 2; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; DRUG DISTRIBUTION; DRUG ELIMINATION; DRUG INHIBITION; DRUG POTENCY; DRUG STRUCTURE; GLUTATHIONE METABOLISM; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; PRIORITY JOURNAL; PROTEIN TRANSPORT;

CATECHOLS; CELL LINE, TRANSFORMED; ESTRADIOL; GLUTATHIONE; HUMANS; KINETICS; LEUKOTRIENE C4; MEMBRANE TRANSPORT PROTEINS; MEMBRANES; MULTIDRUG RESISTANCE-ASSOCIATED PROTEINS; TRANSFECTION; TRITIUM;

MEDA;

EID: 40849139425     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.107.019661     Document Type: Article

References (40)

1. Abel EL, Lyon RP, Bammler TK, Verlinde CL, Lau SS, Monks TJ, and Eaton DL (2004) Estradiol metabolites as isoform-specific inhibitors of human glutathione S-transferases. Chem Biol Interact 151:21-32.
2. Bai F, Jones DC, Lau SS, and Monks TJ (2001) Serotonergic neurotoxicity of 3,4-(±)-methylenedioxyamphetamine and 3,4-(±)- methylendioxymethamphetamine (MDMA) is potentiated by inhibition of γ-glutamyl transpeptidase. Chem Res Toxicol 14:863-870.
3. Bai F, Lau SS, and Monks TJ (1999) Glutathione and N-acetylcysteine conjugates of α-methyldopamine produce serotonergic neurotoxicity: possible role in methylenedioxyamphetamine-mediated neurotoxicity. Chem Res Toxicol 12:1150-1157.
4. 4 express the MRP1 gene-encoded conjugate export pump. Biol Chem 379:1121-1126.
5. Bolton JL, Trush MA, Penning TM, Dryhurst G, and Monks TJ (2000) Role of quinones in toxicology. Chem Res Toxicol 13:135-160.
6. Boumendjel A, Baubichon-Cortay H, Trompier D, Perrotton T, and Di Pietro A (2005) Anticancer multidrug resistance mediated by MRP1: Recent advances in the discovery of reversal agents. Med Res Rev 25:453-472.
7. Butterworth M, Lau SS, and Monks TJ (1996) 17β-Estradiol metabolism by hamster hepatic microsomes: comparison of catechol estrogen O-methylation with catechol estrogen oxidation and glutathione conjugation. Chem Res Toxicol 9:793-799.
8. Butterworth M, Lau SS, and Monks TJ (1998) 2-Hydroxy-4-glutathion-S-yl-17β-estradiol and 2-hydroxy-1-glutathion-S-yl-17β- estradiol produce oxidative stress and renal toxicity in an animal model of 17β-estradiol-mediated nephrocarcinogenicity. Carcinogenesis 19:133-139.
9. Cao K, Devanesan PD, Ramanathan R, Gross ML, Rogan EG, and Cavalieri EL (1998) Covalent binding of catechol estrogens to glutathione catalyzed by horseradish peroxidase, lactoperoxidase, or rat liver microsomes. Chem Res Toxicol 11:917-924.
10. 50) of an enzymatic reaction. Biochem Pharmacol 22:3099-3108.
11. Cui Y, König J, Buchholz U, Spring H, Leier I, and Keppler D (1999) Drug resistance and ATP-dependent conjugate transport mediated by the apical multidrug resistance protein, MRP2, permanently expressed in human and canine cells. Mol Pharmacol 55:929-937.
12. Dallas S, Miller DS, and Bendayan R (2006) Multidrug resistance- associated proteins: expression and function in the central nervous system. Pharmacol Rev 58:140-161.
13. Dantzig AH, Shepard RL, Pratt SE, Tabas LB, Lander PA, Ma L, Paul DC, Williams DC, Peng SB, Slapak CA, et al. (2004) Evaluation of the binding of the tricyclic isoxazole photoaffinity label LY475776 to multidrug resistance associated protein 1 (MRP1) orthologs and several ATP- binding cassette (ABC) drug transporters. Biochem Pharmacol 67:1111-1121.
14. Devanesan P, Santen RJ, Bocchinfuso WP, Korach KS, Rogan EG, and Cavalieri E (2001) Catechol estrogen metabolites and conjugates in mammary tumors and hyperplastic tissue from estrogen receptor-α knock-out (ERKO)/Wnt-1 mice: Implications for initiation of mammary tumors. Carcinogenesis 22:1573-1576.
15. Doherty JA, Weiss NS, Freeman RJ, Dightman DA, Thornton PJ, Houck JR, Voigt LF, Rossing MA, Schwartz SM, and Chen C (2005) Genetic factors in catechol estrogen metabolism in relation to the risk of endometrial cancer. Cancer Epidemiol Biomarkers Prev 14:357-366.
16. Galati G, Sabzevari O, Wilson JX, and O'Brien PJ (2002) Prooxidant activity and cellular effects of the phenoxyl radicals of dietary flavonoids and other polyphenolics. Toxicology 177:91-104.
17. Gekeler V, Ise W, Sanders K, Ulrich W, Beck J (1995) The leukotriene LTD4 receptor antagonist MK571 specifically modulates MRP associated multidrug resistance. Biochem Biophys Res Commun 208:345-352.
18. Haimeur A, Conseil G, Deeley RG, and Cole SPC (2004) The MRP-related and BCRP/ABCG2 multidrug resistance proteins: biology, substrate specificity and regulation. Curr Drug Metab 5:21-53.
19. r 190,000 multidrug resistance protein, MRP, with monoclonal antibodies. Cancer Res 54:5788-5792.
20. Jones DC, Duvauchelle C, Ikegami A, Olsen CM, Lau SS, de la Torre R, and Monks TJ (2005) Serotonergic neurotoxic metabolites of MDMA identified in rat brain. J Pharmacol Exp Ther 313:422-431.
21. König J, Nies AT, Cui Y, Leier I, and Keppler D (1999) Conjugate export pumps of the multidrug resistance protein (MRP) family: localization, substrate specificity, and MRP2-mediated drug resistance. Biochim Biophys Acta 1461:377-394.
22. Koshihara Y, Neichi T, Murota S, Lao A, Fujimoto Y, and Tatsuno T (1984) Caffeic acid is a selective inhibitor for leukotriene biosynthesis. Biochim Biophys Acta 792:92-97.
23. Leslie EM, Bowers RJ, Deeley RG, and Cole SPC (2003) Structural requirements for functional interaction of glutathione tripeptide analogs with the human multidrug resistance protein 1 (MRP1). J Pharmacol Exp Ther 304:643-653.
24. Leslie EM, Deeley RG, and Cole SPC (2005) Multidrug resistance proteins: role of Pglycoprotein, MRP1, MRP2, and BCRP (ABCG2) in tissue defense. Toxicol Appl Pharmacol 204:216-237.
25. Létourneau IJ, Slot AJ, Deeley RG, and Cole SPC (2007) Mutational analysis of a highly conserved proline residue in MRP1, MRP2, and MRP3 reveals a partially conserved function. Drug Metab Dispos 35:1372-1379.
26. Loe DW, Almquist KC, Cole SPC, and Deeley RG (1996a) ATP-dependent 17β-estradiol 17-(β-D-glucuronide) transport by multidrug resistance protein (MRP). inhibition by cholestatic steroids. J Biol Chem 271:9683-9689.
27. Loe DW, Almquist KC, Deeley RG, and Cole SPC (1996b) Multidrug resistance protein (MRP)-mediated transport of leukotriene C4 and chemotherapeutic agents in membrane vesicles. demonstration of glutathione-dependent vincristine transport. J Biol Chem 271:9675-9682.
28. 125I]LY475776. evidence of a major binding site in the COOH-proximal membrane spanning domain. J Biol Chem 277:28690-28699.
29. Mateos R, Goya L, and Bravo L (2006) Uptake and metabolism of hydroxycinnamic acids (chlorogenic, caffeic, and ferulic acids) by HepG2 cells as a model of the human liver. J Agric Food Chem 54:8724-8732.
30. McCann UD and Ricaurte GA (1991) Major metabolites of (±)3,4-methylenedioxyamphetamine (MDA) do not mediate its toxic effects on brain serotonin neurons. Brain Res 545:279-282.
31. Miller RT, Lau SS, and Monks TJ (1996) Effects of intracerebroventricular administration of 5-(glutathion-S-yl)-α-methyldopamine on brain dopamine, serotonin, and norepinephrine concentrations in male Sprague-Dawley rats. Chem Res Toxicol 9:457-465.
32. Moridani MY, Scobie H, and O'Brien PJ (2002) Metabolism of caffeic acid by isolated rat hepatocytes and subcellular fractions. Toxicol Lett 133:141-151.
33. Rogan EG, Badawi AF, Devanesan PD, Meza JL, Edney JA, West WW, Higginbotham SM, and Cavalieri EL (2003) Relative imbalances in estrogen metabolism and conjugation in breast tissue of women with carcinoma: potential biomarkers of susceptibility to cancer. Carcinogenesis 24:697-702.
34. Roy D and Liehr JG (1999) Estrogen, DNA damage and mutations. Mutat Res 424:107-115.
35. Singleton V, Salgues M, Zaya J, and Trousdale E (1985) Caftaric acid disappearance and conversion to products of enzymic oxidation in grape must and wine. Am J Enol Vitic 36:50-56.
36. Stone DM, Stahl DC, Hanson GR, and Gibb JW (1986) The effects of 3,4-methylenedioxymethamphetamine (MDMA) and 3,4-methylenedioxyamphetamine (MDA) on monoaminergic systems in the rat brain. Eur J Pharmacol 128:41-48.
37. Suzuki M, Suzuki H, Sugimoto Y, and Sugiyama Y (2003) ABCG2 transports sulfated conjugates of steroids and xenobiotics. J Biol Chem 278:22644-22649.
38. Wijnholds J, Evers R, van Leusden MR, Mol CA, Zaman GJ, Mayer U, Beijnen JH, van der Valk M, Krimpenfort P, and Borst P (1997) Increased sensitivity to anticancer drugs and decreased inflammatory response in mice lacking the multidrug resistance-associated protein. Nat Med 3:1275-1279.
39. Yue W, Santen RJ, Wang JP, Li Y, Verderame MF, Bocchinfuso WP, Korach KS, Devanesan P, Todorovic R, Rogan EG, et al. (2003) Genotoxic metabolites of estradiol in breast: potential mechanism of estradiol induced carcinogenesis. J Steroid Biochem Mol Biol 86:477-486.
40. Zhang F, Yao D, Hua Y, van Breemen RB, and Bolton JL (2001) Synthesis and reactivity of the catechol metabolites from the equine estrogen, 8,9-dehydroestrone. Chem Res Toxicol 14: 754-763.