4′-epidoxorubicin to re-explore anthracycline degradation in cardiomyocytes

Chemical Research in Toxicology

Volumn 22, Issue 6, 2009, Pages 978-983

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

^a UNIVERSITY CAMPUS BIO MEDICO   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; ANTHRACYCLINE; BAFILOMYCIN A1; DOXORUBICIN; EPIRUBICIN; FERRYLMYOGLOBIN; HYDROGEN PEROXIDE; MALONALDEHYDE; MYOGLOBIN; PROTON TRANSPORTING ADENOSINE TRIPHOSPHATASE; REACTIVE OXYGEN METABOLITE; TERT BUTOXYCARBONYL ALANINE; UNCLASSIFIED DRUG; ALANINE; ANTINEOPLASTIC ANTIBIOTIC; DRUG DERIVATIVE; ENZYME INHIBITOR; MACROLIDE; TERT BUTOXYCARBONYLALANINE; TERT-BUTOXYCARBONYLALANINE;

ANIMAL CELL; ARTICLE; CARDIOTOXICITY; CELL FREE SYSTEM; CELL VIABILITY; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG ACCUMULATION; DRUG DEGRADATION; DRUG DISTRIBUTION; DRUG METABOLISM; HEART MUSCLE CELL; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIPID PEROXIDATION; NONHUMAN; OXIDATIVE STRESS; PROTON TRANSPORT; RAT; ANIMAL; CELL LINE; CHEMISTRY; DRUG EFFECT; METABOLISM; OXIDATION REDUCTION REACTION;

ALANINE; ANIMALS; ANTHRACYCLINES; ANTIBIOTICS, ANTINEOPLASTIC; CELL LINE; DOXORUBICIN; ENZYME INHIBITORS; EPIRUBICIN; HYDROGEN PEROXIDE; MACROLIDES; MYOCYTES, CARDIAC; OXIDATION-REDUCTION; RATS; REACTIVE OXYGEN SPECIES;

EID: 67449087554     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx900039p     Document Type: Article

References (32)

1. Menna, P., Salvatorelli, E., and Minotti, G. (2008) Cardiotoxicity of antitumor drugs. Chem. Res. Toxicol. 15, 1179-1189.
2. Sawyer, D. B., Fukazawa, R., Arstall, M. A., and Kelly, R. A. (1999) Daunorubicin-induced apoptosis in rat cardiac myocytes is inhibited by dexrazoxane. Circ. Res. 84, 257-265. (Pubitemid 29095566)
3. Herman, E. H., Ferrans, V. J., Myers, C. E., and van Vleet, J. F. (1985) Comparison of the effectiveness of (6)-1,2-bis(2,5-deoxopiperanizyl-1-yl)- propane (ICRF-187) and N-acetylcysteine in preventing chronic doxorubicin cardiotoxicity in beagles. Cancer Res. 45, 276-281. (Pubitemid 15196968)
4. 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. (Pubitemid 41079781)
5. 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. (Pubitemid 38720829)
6. 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. (Pubitemid 19100513)
7. Shadle, S. E., Bammel, B. P., Cusack, B. J., Knighton, R. A., Olson, S. J., Mushlin, P. S., and Olson, R. D. (2000) Daunorubicin cardiotoxicity: Evidence for the importance of the quinone moiety in a free-radical-independent mechanism. Biochem. Pharmacol. 60, 1435-1444. (Pubitemid 30742607)
8. Charlier, H. A., Jr., Olson, R. D., Thornock, C. M., Mercer, W. K., Olson, D. R., Broyles, T. S., Muhlestein, D. J., Larson, C. L., Cusack, B. J., and Shadle, S. E. (2005) Investigations of calsequestrin as a target for anthracyclines: Comparison of functional effects of daunorubicin, daunorubicinol, and trifluoperazine. Mol. Pharmacol. 67, 1505-1512. (Pubitemid 40594149)
9. 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. (Pubitemid 44362995)
10. 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. (Pubitemid 35050910)
11. 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. (Pubitemid 38220525)
12. Menna, P., Salvatorelli, E., and Minotti, G. (2007) Doxorubicin degradation in cardiomyocytes. J. Pharmacol. Exp. Ther. 322, 408-419. (Pubitemid 46956366)
13. 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 peroxidase. Cancer Res. 65, 6346-6353. (Pubitemid 40994421)
14. 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. (Pubitemid 47035346)
15. Flogel, U., Godecke, A., Klotz, L. O., and Schrader, J. (2004) Role of myoglobin in the antioxidant defense of the heart. FASEB J. 18, 1156-1158. (Pubitemid 39561555)
16. Witting, P. K., Liao, W.-Q., Matthew, J. H., and Neuzil, J. (2006) Expression of human myoglobin in H9c2 cells enhances toxicity to added hydrogen peroxide. Biochem. Biophys. Res. Commun. 348, 485-493. (Pubitemid 44188595)
17. Gorelik, S., and Kanner, J. (2001) Oxymyoglobin oxidation and membrane lipid peroxidation initiated by iron redox cycle: Prevention of oxidation by enzymic and nonenzymic antioxidants. J. Agric. Food Chem. 49, 5945-5950. (Pubitemid 34062561)
18. 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. (Pubitemid 33151950)
19. Wielinga, P. R., Westerhoff, H. V., and Lankelma, J. (2000) The relative importance of passive and P-glycoprotein mediated anthracycline efflux from multidrug-resistant cells. Eur. J. Biochem. 267, 649-657. (Pubitemid 30082376)
20. Salvatorelli, E., Guarnieri, S., Menna, P., Liberi, G., Calafiore, A. M., Mariggiò, M. A., Mordente, A., Gianni, L., and Minotti, G. (2006) Defective one or two electron reduction of the anticancer anthracycline epirubicin in human heart: Relative importance of vesicular sequestration and impaired efficiency of electron addition. J. Biol. Chem. 281, 10990-11001. (Pubitemid 43855522)
21. Glück, S. (2005) Adjuvant chemotherapy for early breast cancer: Optimal use of epirubicin. Oncologist 10, 780-791. (Pubitemid 43152695)
22. Prasad, M. R., Engelman, R. M., Jones, R. M., and Das, D. K. (1989) Effects of oxyradicals on oxymyoglobin. Deoxygenation, haem removal and iron release. Biochem. J. 263, 731-736. (Pubitemid 19276451)
23. Bowman, F. J., Siebers, A., and Altendorf, K. (1988) Bafilomycins: A class of inhibitors of membrane ATPases from microorganisms, animal cells and plant cells. Proc. Natl. Acad. Sci. U.S.A. 85, 7972-7976. (Pubitemid 18272062)
24. Korchazhkina, O., Exley, C., and Spencer, S. A. (2003) Measurement by reversed-phase high-performance liquid chromatography of malondialdehyde in normal human urine following derivatisation with 2,4-dinitrophenylhydrazine. J. Chromatogr., B: Anal. Technol. Biomed. Life Sci. 794, 353-362. (Pubitemid 37101013)
25. Kluza, J., Marchetti, P., Gallego, M. A., Lancel, S., Fournier, C., Loyens, A., Beauvillain, J. C., and Bailly, C. (2004) Mitochondrial proliferation during apoptosis induced by anticancer agents: Effects of doxorubicin and mitoxantrone on cancer and cardiac cells. Oncogene 23, 7018-7030. (Pubitemid 39319164)
26. L'Ecuyer, T., Sanjeev, S., Thomas, R., Novak, R., Das, L., Campbell, W., and Heide, R. V. (2006) DNA damage is an early event in doxorubicin-induced cardiac myocyte death. Am. J. Physiol. Heart Circ. Physiol. 291, H1273-H1280. (Pubitemid 44343672)
27. Merten, K. E., Jiang, Y., Feng, W., and Kang, Y. J. (2006) Calcineurin activation is not necessary for doxorubicin-induced hypertrophy in H9c2 embryonic rat cardiac cells: Involvement of the phosphoinositide 3-kinase-Akt pathway. J. Pharmacol. Exp. Ther. 319, 934-940. (Pubitemid 44776399)
28. Kaiserová, H., Simůnek, T., van der Vijgh, W. J., Bast, A., and Kvasnicková, E. (2007) Flavonoids as protectors against doxorubicin cardiotoxicity: Role of iron chelation, antioxidant activity and inhibition of carbonyl reductase. Biochim. Biophys. Acta 1772, 1065-1074.
29. Altan, N., Chen, Y., Schindler, M., and Simon, S. M. (1998) Defective acidification in human breast tumor cells and implications for chemotherapy. J. Exp. Med. 187, 1583-1598. (Pubitemid 28235100)
30. Ouar, Z., Bens, M., Vignes, C., Paulais, M., Pringel, C., Fleury, J., Cluzeaud, F., Lacave, R., and Vandewalle, A. (2003) Inhibitors of vacuolar Hu-ATPase impair the preferential accumulation of daunomycin in lysosomes and reverse the resistance to anthracyclines in drug-resistant renal epithelial cells. Biochem. J. 370, 185-193. (Pubitemid 36259431)
31. Lucani, F., Spada, M., De Milito, A., Molinari, A., Rivoltini, L., Montanaro, A., Marra, M., Lugini, L., Logozzi, M., Lozupone, F., Federici, C., Iessi, E., Parmiani, G., Arancia, G., Belardelli, F., and Fais, S. (2004) Effect of proton pump inhibitor pretreatment on resistance of solid tumors to cytotoxic drugs. J. Natl. Cancer Inst. 96, 1702-1713. (Pubitemid 39585639)
32. 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. (Pubitemid 27386100)