Doxorubicin metabolism and toxicity in human myocardium: Role of cytoplasmic deglycosidation and carbonyl reduction

Chemical Research in Toxicology

Volumn 13, Issue 5, 2000, Pages 414-420

  Licata, Sabrina ^a   Saponiero, Antonella ^a   Mordente, Alvaro ^a   Minotti, Giorgio ^b  

^a CATHOLIC UNIVERSITY   (Italy)

^b UNIVERSITY OF CHIETI   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CARBONYL DERIVATIVE; DOXORUBICIN; DOXORUBICINOL; IRON;

ARTICLE; CARDIOTOXICITY; CONTROLLED STUDY; DRUG HYDROLYSIS; DRUG METABOLISM; HUMAN; HUMAN TISSUE; IRON CHELATION; METABOLITE; OXIDATIVE STRESS; REDUCTION;

ALCOHOL OXIDOREDUCTASES; ANTIBIOTICS, ANTINEOPLASTIC; CELL FRACTIONATION; CYTOSOL; DOXORUBICIN; GLYCOSIDES; HEART; HUMANS; MYOCARDIUM; OXIDATION-REDUCTION; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0034119194     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx000013q     Document Type: Article

References (29)

1. Weiss, R. B. (1992) The anthracyclines: will we ever find a better doxorubicin? Semin. Oncol. 19, 670-686.
2. Singal, P. K., Iliskovic, N., Li, T., and Kumar, D. (1997) Adriamycin cardiomyopathy: pathophysiology and prevention. FASEB J. 11, 931-936.
3. van Asperen, J., van Tellingen, O., Tijssen, F., Schinkel, A. H., and Beijnen, J. H. (1999) Increased accumulation of doxorubicin and doxorubicinol in cardiac tissue of mice lacking mdr1a P-glycoprotein. Br. J. Cancer 79, 108-113.
4. Colombo, T., Parisi, I., Zucchetti, M., Sessa, C., Goldhirsch, A., and D'Incalci, M. (1999) Pharmacokinetic interactions of paclitaxel, docetaxel and their vehicles with doxorubicin. Ann. Oncol. 10, 391-395.
5. Olson, R. D., and Mushlin, P. S. (1990) Doxorubicin cardiotoxicity: analysis of prevailing hypotheses. FASEB J. 4, 3076-3086.
6. Minotti, G., Cavaliere, A. F., Mordente, A., Rossi, M., Schiavello, R., Zamparelli, R., and Possati, G. F. (1995) Secondary alcohol metabolites mediate iron delocalization in cytosolic fractions of myocardial biopsies exposed to anticancer anthracyclines. J. Clin. Invent. 95, 1595-1605.
7. Minotti, G., Recalcati, S., Liberi, G., Calafiore, A. M., Mancuso, C., Preziosi, P., and Cairo, G. (1998) The secondary alcohol metabolite of doxorubicin irreversibly inactivates aconitase/iron regulatory protein-1 in cytosolic fractions from human myocardium. FASEB J. 12, 541-551.
8. Takanashi, S., and Bachur, N. R. (1976) Adriamycin metabolism in man. Evidence for urinary metabolism. Drug Metab. Dispos. 4, 79-87.
9. Minotti, G. (1989) Adriamycin dependent release of iron from microsomal membranes. Arch. Biochem. Biophys. 268, 398-403.
10. 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.
11. Stoscheck, C. M. (1990) Quantitation of Protein. Methods Enzymol. 182, 50-68.
12. Forrest, G. L., Akman, S., Doroshow, J. H., Rivera, H., and Kaplan, D. W. (1991) Genomic sequence and expression of a cloned human carbonyl reductase gene with daunorubicin reductase activity. Mol. Pharmacol. 40, 502-510.
13. Powis, G. (1989) Free radical formation by antitumor quinones. Free Radical Biol. Med. 6, 63-101.
14. Brenner, D. E., Galloway, S., Cooper, J., Noone, R., and Hande, K. R. (1985) Improved high-performance liquid chromatography assay of doxorubicin: detection of circulating aglycones in human plasma and comparison with thin-layer chromatography. Cancer Chemother. Pharmacol. 14, 139-145.
15. Gille, L., and Nohl, H. (1997) Analyses of the molecular mechanism of adriamycin-induced cardiotoxicity. Free Radical Biol. Med. 23, 775-782.
16. Minotti, G. (1993) Sources and role of iron in lipid peroxidation. Chem. Res. Toxicol. 6, 134-146.
17. Stewart, D. J., Grewaal, D., Green, R. M., Mikhael, N., Goel, R., Montpetit, V. A., and Redmond, M. D. (1993) Concentrations of doxorubicin and its metabolites in human autopsy heart and other tissues. Anticancer Res. 13, 1945-1952.
18. Beinert, H., and Kennedy, M. C. (1993) Aconitase, a two-faced protein: enzyme and iron regulatory factor. FASEB J. 7, 1442-1449.
19. Hentze, M. W., and Kuhn, L. C. (1996) Molecular control of vertebrate iron metabolism: mRNA based regulatory circuits operated by iron, nitric oxide and oxidative stress. Proc. Natl. Acad. Sci. U.S.A. 93, 8175-8182.
20. Minotti, G., Cairo, G., and Monti, E. (1999) Role of iron in anthracycline cardiotoxicity: new tunes for an old song? FASEB J. 13, 199-212.
21. Kang, Y. J., Chen, Y., and Epstein, P. N. (1996) Suppression of doxorubicin cardiotoxicity by overexpression of catalase in the heart of transgenic mice. J. Biol. Chem. 271, 12610-12616.
22. Siveski-Iliskovic, N., Hill, M., Chow, D. A., and Singal, K. (1995) Probucol protects against adriamycin cardiomyopathy without interfering with its antitumor effect. Circulation 91, 10-15.
23. Herman, E. H., Ferrans, V. J., Myers, C. E., and van Vleet, J. F. (1985) Comparison of the effectiveness of (±)-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.
24. Legha, S. S., Wang, Y, M., Mackay, B., Ewer, M., Hortobagy, G. N., Benjamin, S. R, and Ali, M. K. (1982) Clinical and pharmacologie investigation of the effects of α-tocopherol on adriamycin cardiotoxicity. Ann. N.Y. Acad. Sci. 393, 411-418.
25. Myers, C., Bonow, R., Palmieri, S., Jenkins, J., Corden, B., Locker, G., Doroshow, J., and Epstein, S. A. (1983) A randomized controlled trial assessing the prevention of doxorubicin cardiomyopathy by N-acetylcysteine. Semin. Oncol. 10 (Suppl. 1), 53-55.
26. Kuffel, M. J., Reid, J. M., and Ames, M. M. (1992) Anthracyclines and their C-13 alcohol metabolites: growth inhibition and DNA damage following incubation with tumor cell lines. Cancer Chemother. Pharmacol. 30, 51-57.
27. Smith, T. H., Fujiwara, A. N., and Henry, D. W. (1978) Adriamycin analogues. 2. Synthesis of 13-deoxyanthracyclines. J. Med. Chem. 21, 280-283.
28. Warrell, R. P., Jr. (1986) Aclacinomycin A: clinical development of a novel anthracydine antibiotic in the haematological cancers. Drugs Exp. Clin. Res. 12, 275-282.
29. Rothig, H. J., Kraemer, H. P., and Sedlacek, H. H. (1985) Aclarubicin: experimental and clinical experience. Drugs Exp. Clin. Res. 11, 123-135.