Metabolism is required for the expression of ecstasy-induced cardiotoxicity in vitro

Chemical Research in Toxicology

Volumn 17, Issue 5, 2004, Pages 623-632

  Carvalho, Márcia ^a   Remião, Fernando ^a   Milhazes, Nuno ^a,b   Borges, Fernanda ^a   Fernandes, Eduarda ^a   Do Céu Monteiro, Maria ^b   Gonçalves, Maria José ^b   Seabra, Vítor ^b   Amado, Francisco ^c   Carvalho, Félix ^a   Bastos, Maria Lourdes ^a  

^a UNIVERSITY OF PORTO   (Portugal)

^b CESPU   (Portugal)

^c UNIVERSITY OF AVEIRO   (Portugal)

Author keywords

[No Author keywords available]

Indexed keywords

3,4 METHYLENEDIOXYAMPHETAMINE; 3,4 METHYLENEDIOXYMETHAMPHETAMINE; ADENOSINE DIPHOSPHATE; ADENOSINE TRIPHOSPHATE; ALPHA METHYLDOPAMINE; ALPHA METHYLDOPAMINOCHROME; BIOGENIC AMINE; CALCIUM; CATECHOL DERIVATIVE; GLUTATHIONE; GLUTATHIONE DISULFIDE; GLUTATHIONE PEROXIDASE; GLUTATHIONE REDUCTASE; GLUTATHIONE TRANSFERASE; N METHYL ALPHA METHYLDOPAMINE; N METHYL ALPHA METHYLDOPAMINOCHROME; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CALCIUM CELL LEVEL; CARDIOTOXICITY; CELL STRUCTURE; CELL SUSPENSION; CONCENTRATION (PARAMETERS); CONJUGATION; CONTROLLED STUDY; DRUG ABUSE; ENZYME ACTIVITY; EXPOSURE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HOMEOSTASIS; IN VITRO STUDY; MALE; METABOLISM; METABOLITE; NONHUMAN; OXIDATION; RAT;

3,4-METHYLENEDIOXYAMPHETAMINE; ADENOSINE DIPHOSPHATE; ADENOSINE TRIPHOSPHATE; ANIMALS; CALCIUM; CELL SURVIVAL; CELLS, CULTURED; DEOXYEPINEPHRINE; GLUTATHIONE; GLUTATHIONE DISULFIDE; GLUTATHIONE PEROXIDASE; GLUTATHIONE REDUCTASE; GLUTATHIONE TRANSFERASE; METABOLISM; MYOCYTES, CARDIAC; RATS; SEROTONIN AGENTS; TIME FACTORS;

ANIMALIA; MEDA;

EID: 2442639021     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx049960f     Document Type: Article

References (50)

1. Henry, J. A., Jeffreys, K. J., and Dawling, S. (1992) Toxicity and deaths from 3,4-methylenedioxymethamphetamine ("ecstasy"). Lancet 340, 384-387.
2. Milroy, C. M., Clark, J. C., and Forrest, A. R. W. (1996) Pathology of deaths associated with "ecstasy" and "eve" misuse. J. Clin. Pathol. 49, 149-153.
3. Suarez, R., and Riemersma, R. (1988) "Ecstasy" and sudden cardiac death. Am. J. Forensic Med. Pathol. 9, 339-341.
4. O'Cain, P., Hletko, S., Ogden, B., and Varner, K. (2000) Cardiovascular and sympathetic responses and reflex changes elicited by MDMA. Physiol. Behav. 70, 141-148.
5. Lester, S. J., Baggott, M., Welm, S., Schiller, N. B., Jones, R. T., Foster, E., and Mendelson, J. (2000) Cardiovascular effects of 3,4-methylenedioxymethamphetamine. A double-blind, placebo-controlled trial. Ann. Intern. Med. 133, 969-973.
6. Fitzgerald, J. L., and Reid, J. J. (1994) Sympathomimetic actions of methylenedioxymethamphetamine in rat and rabbit isolated cardiovascular tissues. J. Pharm. Pharmacol. 46, 826-832.
7. Varner, K. Y., Delcarpio, J. B., and Moerschbaecher, J. M. (1998) Cardiac toxicity elicited by repeated administration of 3,4-methyl-enedioxymethamphetamine (MDMA). NIDA Res. Monogr. 179, 214.
8. Rona, G. (1985) Catecholamine cardiotoxicity. J. Mol. Cell Cardiol. 17, 291-306.
9. Wheatley, A. M., Thandroyen, F. T., and Opie, L. H. (1985) Catecholamine-induced myocardial cell damage: catecholamines or adrenochrome? J. Mol. Cell Cardiol. 17, 349-359.
10. Gesi, M., Lenzi, P., Soldani, P., Ferrucci, M., Giusiani, A., Fornai, F., and Paparelli, A. (2002) Morphological effects in the mouse myocardium after methylenedioxymethamphetamine administration combined with loud noise exposure. Anat. Rec. 267, 37-46.
11. He, S. Y. (1995) Methamphetamine-induced toxicity in cultured adult rat cardiomyocytes. Nippon Hoigaku Zasshi 49, 175-186.
12. Bai, F., Lau, S. S., and Monks, T. J. (1999) Glutathione and N-acetylcysteine conjugates of α-Methyldopamine produce serotoninergic neurotoxicity: possible role in methylenedioxyamphet-amine-mediated neurotoxicity. Chem. Res. Toxicol. 12, 1150-1157.
13. Bai, F., Jones, D. C., Lau, S. S., and Monks, T. J. (2001) Serotonergic Neurotoxicity of 3,4-(±)-Methylenedioxyamphet-amine and 3,4-(±)-Methylenedioxymethamphetamine (Ecstasy) Is Potentiated by Inhibition of gamma-Glutamyl Transpeptidase. Chem. Res. Toxicol. 14, 863-870.
14. Miller, R. T., Lau, S. S., and Monks, T. J. (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.
15. Miller, R. T., Lau, S. S., and Monks, T. J. (1997) 2,5-bis-(Glutathion-S-yl)-α-Methyldopamine, a putative metabolite of (±)-3,4-methylenedioxyamphetamine, decreases brain serotonin concentrations. Eur. J. Pharmacol. 323, 173-180.
16. Carvalho M., Milhazes, N., Remião, F., Borges, F., Fernandes, E., Monks, T., Amado, F., Carvalho, F., and Bastos, M. L. (2004) Hepatotoxicity of 3,4-methylenedioxyamphetamine and α-Methyldopamine in isolated rat hepatocytes: formation of glutathione conjugates. Arch. Toxicol. 78, 16-24.
17. Carvalho, M., Hawksworth, G., Milhazes, N., Borges, F., Monks, T., 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.
18. Lim, H. K., and Foltz, R. L. (1988) In vivo and in vitro metabolism of 3,4-(methylenedioxy)methamphetamine in the rat: identification of metabolites using an ion trap detector. Chem. Res. Toxicol. 1, 370-378.
19. Kumagai, Y., Lin, L. Y., Schmitz, D. A., and Cho, A. K. (1991) Hydroxyl radical mediated demethylenation of (methylenedioxy)-phenyl compounds. Chem. Res. Toxicol. 4, 330-334.
20. Marquardt, G. M., DiStefano, V., and Ling, L. L. (1978) Metabolism of beta-3,4-methylenedioxyamphetamine in the rat. Biochem. Pharmacol. 27, 1503-1505.
21. Bolton, J. L., Trush, M. A., Penning, T. M., Dryhurst, G., and Monks, T. J. (2000) Role of quinones in toxicology. Chem. Res. Toxicol. 13, 135-160.
22. Bindoli, A., Rigobello, M. P., and Galzigna, L. (1989) Toxicity of aminochromes. Toxicol. Lett. 48, 3-20.
23. 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.
24. Hiramatsu, M., Kumagai, Y., Unger, S. E., and Cho, A. K. (1990) Metabolism of methylenedioxymethamphetamine: formation of dihydroxymethamphetamine and a quinone identified as its glutathione adduct. J. Pharmacol. Exp. Ther. 254, 521-527.
25. Remião, F., Carmo, H., Carvalho, F., and Bastos, M. L. (2001) Cardiotoxicity studies using freshly isolated calcium-tolerant cardiomyocytes from adult rat. In Vitro Cell Dev. Biol. Anim. 37, 1-4.
26. Remião, F., Carvalho, M., Carmo, H., Carvalho, F. D., and Bastos, M. L. (2002) Cu2+-induced isoproterenol oxidation into isoprenochrome in adult rat calcium-tolerant cardiomyocytes. Chem. Res. Toxicol. 15, 861-869.
27. Stocchi, V., Cucchiarini, L., Magnani, M., Chiarantini, L., Palma, P., and Crescentini, G. (1985) Simultaneous extraction and reverse-phase high-performance liquid chromatographic determination of adenine and pyridine nucleotides in human red blood cells. Anal. Biochem. 146, 118-124.
28. Carvalho, M., Carvalho, F., Remião, F., Pereira, M. L., Pires-das-Neves, R., and Bastos, M. L. (2002) Effect of 3,4-methylene-dioxymethamphetamine ("ecstasy") on body temperature and liver antioxidant status in mice: influence of ambient temperature. Arch. Toxicol. 76, 166-172.
29. Boston, D., Koyama, T., Rodriguez-Larrain, J., Zou, A., Su, Z., and Barry, W. (1998) Effects of angiotensin II on intracellular calcium and contracture in metabolically inhibited cardiomyocytes. J. Pharmacol. Exp. Ther. 285, 716-723.
30. DiVirgilio, F., Steinberg, T. H., and Silverstein, S. C. (1990) Inhibition of Fura-2 sequestration and secretion with organic anion transport blockers. Cell Calcium 11, 57-62.
31. Lemos-Amado, F., Domingues, P., Ferrer-Correia, A., Remião, F., Milhazes, N., Borges, F., Carvalho, F. D., and Bastos, M. L. (2001) Electrospray tandem mass spectrometry of aminochromes. Rapid Commun. Mass Spectrom. 15, 2466-2471.
32. Kreth, K.-P., Kovar, K.-A., Schwab, M., and Zanger, U. M. (2000) Identification of the human cytochromes P450 involved in the oxidative metabolism of "ecstasy"-related designer drugs. Biochem. Pharmacol. 59, 1563-1571.
33. Chavdarian, C. G., Karashima, D., Castagnoli, N. J., and Hundley, H. K. (1978) Oxidative and cardiovascular studies on natural and synthetic catecholamines. J. Med. Chem. 21, 548-554.
34. Zhang, F., and Dryhurst, G. (1994) Effects of L-cysteine on the oxidation chemistry of dopamine: new reaction pathways of potential relevance to idiopathic Parkinson's disease. J. Med. Chem. 37, 1084-1098.
35. Carstam, R., Brinck, C., Hindemith-Augustsson, A., Rorsman, H., and Rosengren, E. (1991) The neuromelanin of the human substancia nigra. Biochim. Biophys. Acta 1097, 152-160.
36. Hegedus, Z. L. (2000) The probable involvement of soluble and deposited melanins, their intermediates and the reactive oxygen side-products in human diseases and aging. Toxicology 145, 85-101.
37. Ben-Shachar, D., Riederer, P., and Youdim, M. B. (1991) Iron-melanin interaction and lipid peroxidation: implications for Parkinson's disease. J. Neurochem. 57, 1609-1614.
38. DiMascio, P., Murphy, M. E., and Sies, H. (1991) Antioxidant defense systems: the role of carotenoids, tocopherols, and thiols. Am. J. Clin. Nutr. 53, 194S-200S.
39. Ommen, B. V., Ploemen, J. H. T. M., Bogaards, J. J. P., Monks, T. J., Lau, S. S., and Bladeren, P. J. V. (1991) Irreversible inhibition of rat glutathione S-transferase 1-1 by quinones and their glutathione conjugates. Structure-activity relationship and mechanism. Biochem. J. 276, 661-666.
40. Monks, T. J., and Lau, S. S. (1992) Toxicology of quinonethioethers. Crit. Rev. Toxicol. 22, 243-270.
41. Remiã, F., Carmo, H., Carvalho, F. D., and Bastos, M. L. (1999) Inhibition of glutathione reductase by isoproterenol oxidation products. J. Enzyme Inhib. 15, 47-61.
42. Timerman, A. P., Altschuld, R. A., Hohl, C. M., Brierley, G. P., and Merola, A. J. (1990) Cellular glutathione and the response of adult rat heart myocytes to oxidant stress. J. Mol. Cell Cardiol. 22, 565-575.
43. Kang, Y. J. (2001) Molecular and cellular mechanisms of cardiotoxicity. Environ. Health Perspect. 109, 27-34.
44. Orrenius, S., McConkey, D. J., Bellomo, G., and Nicotera, P. (1989) Role of Ca2+ in toxic cell killing. TIPS 10, 281-285.
45. Taam, G. M., Takeo, S., Ziegelhoffer, A., Singal, P. K., Beamish, R. E., and Dhalla, N. S. (1986) Effect of adrenochrome on adenine nucleotides and mitochondrial oxidative phosphorylation in rat heart. Can. J. Cardiol. 2, 88-93.
46. Haworth, R. (1990) Use of isolated adult myocytes to evaluate cardiotoxicity. II. Preparation and properties. Toxicol. Pathol. 18, 521-530.
47. Dhanbhoora, C. M., and Babson, J. R. (1992) Thiol depletion induces lethal cell injury in cultured cardiomiocytes. Arch. Biochem. Biophys. 293, 130-139.
48. Garcia-Repetto, R., Moreno, E., Soriano, T., Jurado, C., Gimenez, M. P., and Menendez, M. (2003) Tissue concentrations of MDMA and its metabolite MDA in three fatal cases of overdose. Forensic Sci. Int. 135, 110-114.
49. Sticht, G., Pluisch, F., Bierhoff, E., and Kaferstein, H. (2003) Fatal outcome of Ecstasy overdose. Arch. Kriminol. 211, 73-80.
50. Segura, M., Ortuno, J., Farre, M., McLure, J. A., Pujadas, M., Pizarro, N., Llebaria, A., Joglar, J., Roset, P. N., Segura, J., and Torre, R. d. L. (2001) 3,4-Dihydroxymethamphetamine (HHMA). A major in vivo 3,4-methylenedioxymethamphetamine (MDMA) metabolite in humans. Chem. Res. Toxicol. 14, 1203-1208.