Anthracycline degradation in cardiomyocytes: A journey to oxidative survival

Chemical Research in Toxicology

Volumn 23, Issue 1, 2010, Pages 6-10

  Menna, Pierantonio ^a   Salvatorelli, Emanuela ^a   Minotti, Giorgio ^a  

^a UNIVERSITY CAMPUS BIO MEDICO   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

5 IMINODAUNORUBICIN; CREATINE KINASE; DAUNORUBICIN; DOXORUBICIN; EPIRUBICIN; HYDROGEN PEROXIDE; HYDROQUINONE; IDARUBICIN; MYOGLOBIN; PHTHALIC ACID; QUINONE DERIVATIVE; REACTIVE OXYGEN METABOLITE; SUCCINATE DEHYDROGENASE; SUPEROXIDE;

BONE MARROW TOXICITY; CARDIOTOXICITY; CATALYST; CELL DEATH; CELL SURVIVAL; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHROMATOPHORE; CONGESTIVE CARDIOMYOPATHY; CONGESTIVE HEART FAILURE; DRUG DEGRADATION; DRUG OXIDATION; HEART MUSCLE CELL; LONG TERM CARE; OXIDATION REDUCTION REACTION; OXIDATIVE STRESS; REVIEW;

ANTHRACYCLINES; ANTIBIOTICS, ANTINEOPLASTIC; APOPTOSIS; DOXORUBICIN; MYOCYTES, CARDIAC; MYOGLOBIN; OXIDATION-REDUCTION; OXIDATIVE STRESS; REACTIVE OXYGEN SPECIES;

EID: 75149193249     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx9003424     Document Type: Review

References (27)

1. Myers, C. E., McGuire, W. P., Liss, R. H., Ifrim, I., Grotzinger, K., and Young, R. C. (1977) Adriamycin: the role of lipid peroxidation in cardiac toxicity and tumor response. Science 197, 165-167.
2. Mariam, Y. H., and Sawyer, A. (1996) A computational study on the relative reactivity of reductively activated 1,4-benzoquinone and its isoelectronic analogs. J. Comput.-Aided Mol. Des. 10, 441-460.
3. Reszka, K. J., McCormick, M. L., and Britigan, B. E. (2001) Peroxidase- and nitrite-dependent metabolism of the anthracycline anticancer agents daunorubicin and doxorubicin. Biochemistry 40, 15349-15361.
4. Miura, T., Muraoka, S., and Fujimoto, Y. (2000) Inactivation of creatine kinase by adriamycin during interaction with horseradish peroxidase. Biochem. Pharmacol. 60, 95-99.
5. Muraoka, S., and Miura, T. (2003) Inactivation of mitochondrial succinate dehydrogenase by adriamycin activated by horseradish peroxidase and hydrogen peroxide. Chem.-Biol. Interact. 145, 67-75.
6. Menna, P., Salvatorelli, E., Giampietro, R., Liberi, G., Teodori, G., Calafiore, A. M., and Minotti, G. (2002) Doxorubicin-dependent reduction of ferrylmyoglobin and inhibition of lipid peroxidation: implications for cardiotoxicity of anticancer anthracyclines. Chem. Res. Toxicol. 15, 1179-1189.
7. Cartoni, A., Menna, P., Salvatorelli, E., Braghiroli, D., Giampietro, R., Animati, F., Urbani, A., Del Boccio, P., and Minotti, G. (2004) Oxidative degradation of cardiotoxic anticancer anthracyclines to phthalic acids: Novel function for ferrylmyoglobin? J. Biol. Chem. 279, 5088-5099.
8. Taatjes, D. J., Gaudiano, G., Resing, K., and Koch, T. H. (1997) Redox pathway leading to the alkylation of DNA by the anthracycline antitumor drugs adriamycin and daunomycin. J. Med. Chem. 40, 1276-1286.
9. Alexander, J., Bhatia, A. V., Mitscher, L. A., Omoto, S., and Suzuki, T. (1980) Methylation and hydroxylation studies on aloe-emodin. J. Org. Chem. 45, 20-24.
10. Kim, K. S., Vanotti, E., Suarato, A., and Johnson, F. (1979) Anthracyclines and related substances. 2. An efficient and regiospecific synthesis of DL-7,9dideoxydaunomycinone. J. Am. Chem. Soc. 101, 2483-2484.
11. Egawa, T., Shimada, H., and Ishimura, Y. (2000) Formation of compound I in the reaction of native myoglobins with hydrogen peroxide. J. Biol. Chem. 275, 34858-34866.
12. Menna, P., Salvatorelli, E., and Minotti, G. (2007) Doxorubicin degradation in cardiomyocytes. J. Pharmacol. Exp. Ther. 322, 408-419.
13. Trost, L. C., and Wallace, K. B. (1994) Adriamycin-induced oxidation of myoglobin. Biochem. Biophys. Res. Commun. 204, 30-37.
14. Yackzan, K. S., and Wingo, W. J. (1982) Transport of fatty acids by myoglobin: A hypothesis. Med. Hypotheses 8, 613-618.
15. Menna, P., Salvatorelli, E., and Minotti, G. (2008) Cardiotoxicity of antitumor drugs. Chem. Res. Toxicol. 15, 1179-1189.
16. Reszka, K. J., Wagner, B. A., Teesch, L. M., Britigan, B. E., Spitz, D. R., and Burns, C. P. (2005) Inactivation of anthracyclines by cellular peroxidases. Cancer Res. 65, 6346-6353.
17. Wagner, B. A., Teesch, L. M., Buettner, G. R., Britigan, B. E., Burns, C. P., and Reszka, K. J. (2007) Inactivation of anthracyclines by serum heme proteins. Chem. Res. Toxicol. 20, 920-926.
18. Minotti, G., Recalcati, S., Menna, P., Salvatorelli, E., Corna, G., and Cairo, G. (2004) Doxorubicin cardiotoxicity and the control of iron metabolism: Quinone dependent and independent mechanisms. Methods Enzymol. 378, 340-361.
19. Minotti, G., Menna, P., Salvatorelli, E., Cairo, G., and Gianni, L. (2004) Anthracyclines: Molecular advances and pharmacologic developments in antitumor activity and cardiotoxicity. Pharmacol. Rev. 56, 185-229.
20. Menna, P., Salvatorelli, E., and Minotti, G. (2009) 4′- Epidoxorubicin to reexplore anthracycline degradation in cardiomyocytes. Chem. Res. Toxicol. 22, 978-983.
21. Ladas, E. J., Jacobson, J. S., Kennedy, D. D., Teel, K., Fleischauer, A., and Kelly, K. M. (2004) Antioxidants and cancer therapy: A systematic review. J. Clin. Oncol. 22, 517-528.
22. Shi, R., Huang, C. C., Aronstam, R. S., Ercal, N., Martin, A., and Huang, Y. W. (2009) N-acetylcysteine amide decreases oxidative stress but not cell death induced by doxorubicin in H9c2 cardiomyocytes. BMC Pharmacol. 9, 7.
23. Salvatorelli, E., Menna, P., Lusini, M., Covino, E., and Minotti, G. (2009) Doxorubicinolone formation and efflux: A salvage pathway against epirubicin accumulation in human heart. J. Pharmacol. Exp. Ther. 329, 175-184.
24. Marcillat, O., Zhang, Y., and Davies, K. J. (1989) Oxidative and non-oxidative mechanisms in the inactivation of cardiac mitochondrial electron transport chain components by doxorubicin. Biochem. J. 259, 181-189.
25. Tokarska-Schlattner, M., Zaugg, M., Zuppinger, C., Wallimann, T., and Schlattner, U. (2006) New insights into doxorubicin-induced cardiotoxicity: The critical role of cellular energetics. J. Mol. Cell. Cardiol. 41, 389-405.
26. Jeyaseelan, R., Poizat, C., Baker, R. K., Abdishoo, S., Isterabadi, L. B., Lyons, G. E., and Kedes, L. (1997) A novel cardiac-restricted target for doxorubicin: CARP, a nuclear modulator of gene expression in cardiac progenitor cells and cardiomyocytes. J. Biol. Chem. 272, 22800-22808.
27. Gianni, L., Herman, E. H., Lipshultz, S. E., Minotti, G., Sarvazyan, N., and Sawyer, D. B. (2008) Anthracycline cardiotoxicity: From bench to bedside. J. Clin. Oncol. 26, 3777-3784.