Cross-functioning between the extraneuronal monoamine transporter and multidrug resistance protein 1 in the uptake of adrenaline and export of 5-(Glutathion-S-yl)adrenaline in rat cardiomyocytes

Chemical Research in Toxicology

Volumn 22, Issue 1, 2009, Pages 129-135

  Costa, Vera Marisa ^a   Ferreira, Luísa Maria ^b   Branco, Paula Sério ^b   Carvalho, Félix ^a   Bastes, Maria Lourdes ^a   Carvalho, Rui Albuquerque ^c   Carvalho, Márcia ^a,d   Remião, Fernando ^a  

^a UNIVERSITY OF PORTO   (Portugal)

^b UNIVERSIDADE NOVA DE LISBOA   (Portugal)

^c UNIVERSITY OF COIMBRA   (Portugal)

^d UNIVERSIDADE FERNANDO PESSOA   (Portugal)

Author keywords

[No Author keywords available]

Indexed keywords

5 (GLUTATHION S YL)ADRENALINE; ADRENALIN; CATECHOLAMINE; CORTICOSTERONE; ELACRIDAR; EXTRANEURONAL MONOAMINE TRANSPORTER; GLYCOPROTEIN P; MONOAMINE; MULTIDRUG RESISTANCE PROTEIN 1; QUINIDINE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CELL ISOLATION; CELL TRANSFER; EFFUSION; HEART MUSCLE CELL; INHIBITION KINETICS; MALE; MEMBRANE TRANSPORT; METABOLITE; NONHUMAN; OXIDATION; RAT;

RATTUS;

EID: 61849145099     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx8002577     Document Type: Article

References (48)

1. 2+-induced isoproterenol oxidation into isoprenochrome in adult rat calcium-tolerant cardiomyocytes. Chem. Res. Toxicol. 15, 861-869.
2. Bindoli, A., Rigobello, M. P., and Deeble, D. J. (1992) Biochemical and toxicological properties of the oxidation products of catecholamines. Free Radical Biol. Med. 13, 391-405.
3. Dhalla, S. N., Sasaki, H., Mochizuki, S., Dhalla, S. K., Liu, X., and Elimban, V. (2001) Catecholamine-induced cardiomyopathy. In Cardiovascular Toxicology (Acosta, D. J., Ed.) pp 269-318, Taylor and Francis, London.
4. Flaherty, J. T. (1991) Myocardial injury mediated by oxygen free radical. Am. J. Med. 91, 79S-88S.
5. Costa, V. M., Silva, R., Ferreira, L. M., Branco, P. S., Carvalho, F., Bastos, M. L., Carvalho, R. A., Carvalho, M., and Remião, F. (2007) Oxidation process of adrenaline in freshly isolated rat cardiomyocytes: Formation of adrenochrome, quinoproteins and GSH-adduct. Chem. Res. Toxicol. 20, 1183-1191.
6. Carvalho, M., Remião, F., Milhazes, N., Borges, F., Fernandes, E., Monteiro, M. C, Goncalves, M. J., Seabra, V., Amado, F., Carvalho, F., and Bastos, M. L. (2004) Metabolism is required for the expression of ecstasy-induced cardiotoxicity in vitro. Chem. Res. Toxicol. 17,623-632.
7. Remião, F., Carmo, H., Carvalho, F., and Bastos, M. L. (2001) Copper enhances isoproterenol toxicity in isolated rat cardiomyocytes. Car-diovasc. Toxicol. I, 195-204.
8. Remião, F., Rettori, D., Han, D., Carvalho, F., Bastos, M. L., and Cadenas, E. (2004) Leucoisoprenochrome-o-semiquinone formation in freshly isolated adult rat cardiomyocytes. Chem. Res. Toxicol. 17, 1584-1590.
9. Monks, T. J., and Lau, S. S. (1992) Toxicology of quinone-thioethers. Crit. Rev. Toxicol. 22, 243-270.
10. Monks, T. J., and Lau, S. S. (1997) Biological reactivity of polyphe-nolic-glutathione conjugates. Chem. Res. Toxicol. 10, 1296-1313.
11. Spencer, J. P. E., Jenner, P., Daniel, S. E., Lees, A. J., Marsden, D. C, and Halliwell, B. (1998) Conjugates of catecholamines with cysteine and GSH in Parkinson's disease: Possible mechanism of formation involving reactive oxygen species. J. Neurochem. 71, 2112-2122.
12. Spencer, J. P. E., Whiteman, M., Jenner, P., and Halliwel, B. (2002) 5-S-Cysteinyl-conjugates of catecholamines induce cell damage, extensive DNA base modication and increases in caspase-3 activity in neurons. J. Neurochem. 81, 122-129.
13. Carvalho, M., Hawksworth, G., Milhazes, N., Borges, F., Monks, T. J., Fernandes, E., Carvalho, F., and Bastos, M. L. (2002) Role of metabolites in MDMA (ecstasy)-induced nephrotoxicity: An in vitro study using rat and human renal proximal tubular cells. Arch. Toxicol. 76, 581-588.
14. Capela, J. P., Meisel, A., Abreu, A. R., Branco, P. S., Ferreira, L. M., Lobo, A. M., Remiao, F., Bastos, M. L., and Carvalho, F. (2006) Neurotoxicity of ecstasy metabolites in rat cortical neurons and influence of hyperthermia. J. Pharmacol. Exp. Ther. 316, 53-61.
15. Capela, J. P., Macedo, C, Branco, P. S., Ferreira, L. M., Lobo, A., Fernandes, E., Remião, F., Bastos, M. L., Dirnagl, U., Meisel, A., and Carvalho, F. (2007) Neurotoxicity mechanisms of Another ecstasy metabolites. Neuroscience 146, 1743-1757.
16. LaVoie, M. J., and Hastings, T. G. (1999) Dopamine quinone formation and protein modification associated with the striatal neurotoxicity of methamphetamine: evidence against a role for extracellular dopamine. J. Neurosci. 19, 1484-1491.
17. Ghosh, S., Ting, S., Lau, H., Pulinilkunnil, T., An, D., Qi, D., Abraham, M. A., and Rodrigues, B. (2004) Increased efflux of glutathione conjugate in acutely diabetic cardiomyocytes. Can. J. Physiol. Pharmacol. 82, 879-887.
18. Juliano, R. L., and Ling, V. (1976) A surface glycoprotein modulating drug permeability in Chinese hamster ovary cell mutants. Biochim. Biophys. Acta 455, 152-162.
19. Cole, S. P., Bhardwaj, G., Gerlach, J. H., Mackie, J. E., Grant, C. E., Almquist, K. C., Stewart, A. J., Kurz, E. U., Duncan, A. M., and Deeley, R. G. (1992) Overexpression of a transporter gene in a multidrug resistant human lung cancer cell line. Science 258, 1650-1654.
20. Allikmets, R., Schriml, L. M., Hutchinson, A., Romano-Spica, V., and Dean, M. (1998) A human placenta-specific ATP-binding cassette gene (ABCP) on chromosome 4q22 that is involved in multidrug resistance. Cancer Res. 58, 5337-5339.
21. Borst, P., and Elferink, O. R. (2002) Mammalian ABC transporters in health and disease. Annu. Rev. Biochem. 71, 537-592.
22. Schinkel, A. H., and Jonker, J. W. (2003) Mammalian drug efflux transporters of the ATP binding cassette (ABC) family: An overview. Adv. Drug Delivery Rev. 55, 3-29.
23. Ballatori, N., Hammond, C. L., Cunningham, J. B., Krance, S. M., and Marchan, R. (2005) Molecular mechanisms of reduced glutathione transport: role of the MRP/CFTR/ABCC and OATP/SLC21A families of membrane proteins. Toxicol. Appl. Pharmacol. 204, 238-255.
24. Leslie, E. M., Deeley, R. G., and Cole, S. P. (2007) Multidrug resistance proteins: Role of P-glycoprotein, MRP1, MRP2 and BCRP (ABCG2) in tissue defense. Toxicol. Appl. Pharmacol. 204,216-227.
25. McDevitt, C. A., and Callaghan, R. (2007) How can we best structure information on P-glycoprotein to design inhibitors? Pharmacol. Ther. 113, 429-441.
26. Cole, S. P. C, and Deeley, R. G. (2006) Transport of glutathione and glutathione conjugates by MRP1. Trends Pharmacol. Sci. 27, 438-446.
27. Eisenhofer, G. (2001) The role of neuronal and extraneuronal plasma membrane transporters in the inactivation of peripheral catecholamines. Pharmacol. Ther. 91, 35-62.
28. Iversen, L. L. (1965) The uptake of catecholamines at high perfusion concentrations in the rat isolated heart: A novel catecholamine uptake process. Br. J. Pharmacol. 24, 18-33.
29. Malmfors, T. (1967) Fluorescence histochemical studies on the uptake, storage, and release of catecholamines. Circ. Res. XX-XXI, 11125-11142.
30. Westfall, T. C, and Westfall, D. P. (2006) Adrenergic agonists and antagonists. In Goodman & Gilman's The Pharmacological Basis of Therapeutics (Brunton, L. L., Lazo, J. S., and Parker, K. L., Eds.) McGraw-Hill, New York.
31. Engel, K., and Wang, J. (2005) Interaction of organic cations with a newly identified plasma membrane monoamine transporter. Mol. Pharmacol. 68, 1397-1407.
32. Engel, K., Zhou, M., and Wang, J. (2004) Identification and characterization of a novel monoamine transporter in the human brain. J. Biol. Chem. 279, 50042-50049.
33. Silva, R., Boldt, S., Costa, V. M., Carmo, H., Carvalho, M., Carvalho, F., Bastos, M. L., Lemos-Amado, F., and Remiao, F. (2007) Evaluation of GSH adducts of adrenaline in biological samples. Biomed. Chro-matogr. 21, 670-679.
34. Varma, M. V. S., Sarkar, M., Kapoor, N., and Panchagnula, R. (2005) pH-dependents functional activity of P-glycoprotein in limiting intestinal absorption of protic drugs 1. Simultaneous determination of quinidine and markers in rat in situ perfusion samples. J. Chro-matogr. B 816, 243-249.
35. 2 in isolated cardiac myocytes. Mol. Cell. Biochem. 163-164, 181-183.
36. Carvalho, M., Milhazes, N., Remiao, F., Borges, F., Fernandes, E., Amado, F., Monks, T. J., Carvalho, F., and Bastos, M. L. (2004) Hepatotoxicity of 3,4-methylenedioxyamphetamine and alpha-meth-yldopamine in isolated rat hepatocytes: formation of glutathione conjugates. Arch. Toxicol. 78, 16-24.
37. Declèves, X., Niel, E., Debray, M., and Scherrmann, J.-M. (2006) Is P-glycoprotein (ABCB1) a phase 0 or a phase 3 colchicine transporter depending on colchicine exposure conditions? Toxicol. Appl. Pharmacol. 217, 153-160.
38. Schutte, M. E., Freidig, A. P., van de Sandt, J. J. M., Alink, G. M., Rietjens, I. M. C. M., and Groten, J. P. (2006) An in vitro and in silico study on the flavonoid-mediated modulation of the transport of 2-amino-l-methyl-6- phenylimidazo[4,5-b]pyridine (PhIP) through Ca-co-2 monolayers. Toxicol. Appl. Pharmacol. 217, 204-215.
39. Gruber, A., Larsson, R., Nygren, P., Björkholm, M., and Peterson, C. (1994) A non-P-glycoprotein-mediated mechanism of vincristine transport which is affected by resistance modifiers and present in chemosensitive cells. Leukemia 8, 985-989.
40. Meissner, K., Sperker, B., Karsten, C, zu Schwabedissen, H. M., Seeland, U., Bohm, M., Bien, S., Dazert, P., Kunert-Keil, C, Vogelgesang, S., Warzok, R., Siegmund, W., Cascorbi, I., Wendt, M., and Kroemer, H. K. (2002) Expression and localization of P-glycoprotein in human heart: effects of cardiomyopathy. J. Histochem. Cytochem. 50, 1351-1356.
41. Lazarowski, A. J., Garcia Rivello, H. J., Vera Janavel, G. L., Cuniberti, L. A., Cabeza Meckert, P. M., Yannarelli, G. G., Mele, A., Crottogini, A. J., and Laguens, R. P. (2005) Cardiomyocytes of chronically ischemic pig hearts express the MDR-1 gene-encoded P-glycoprotein. J. Histochem. Cytochem. 53, 845-850.
42. Laguens, R. P., Lazarowski, A. J., Cuniberti, L. A., Vera Janavel, G. L., Cabeza Meckert, P. M., Yannarelli, G. G., del Valle, H. F., Lascano, E. C., Negroni, J. A., and Crottogini, A. J. (2007) Expression of the MDR-1 gene-encoded P-glycoprotein in cardiomyocytes of conscious sheep undergoing acute myocardial ischemia followed by reperfusion. J Histochem. Cytochem. 55, 191-197.
43. Estevez, M. D., Wolf, A., and Schramm, U. (2000) Effect of PSC 833, verapamil and amiodarone on adriamycin toxicity in cultured rat cardiomyocytes. Toxicol in Vitro 14, 17-23.
44. Sukhai, M., and Piquette-Miller, M. (2000) Regulation of the multidrug resistance genes by stress signals. Pharm. Pharm. Sci. 3, 268-280.
45. Goldstein, D. S. (2003) Catecholamines and stress. Endocr. Regul. 37, 69-80.
46. Goldstein, D. S., Eisenhofer, G., and Kopin, I. J. (2003) Sources and significance of plasma levels of catechols and their metabolites in humans. J. Pharmacol. Exp. Ther. 305, 800-811.
47. Yang, C. P., DePinho, S. G., Greenberger, L. M., Arceci, R. J., and Horwitz, S. B. (1989) Progesterone interacts with P-glycoprotein in multidrug-resistant cells and in the endometrium of gravid uterus. J. Biol. Chem. 264, 782-788.
48. Shirasaka, Y., Sakane, T., and Yamashita, S. (2006) Effect of P-glycoprotein expression levels on the concentration-dependent permeability of drugs to the cell membrane. J. Pharm. Sci. 97, 553-565.