Oxidative degradation of cardiotoxic anticancer anthracyclines to phthalic acids: Novel function for ferrylmyoglobin

Journal of Biological Chemistry

Volumn 279, Issue 7, 2004, Pages 5088-5099

  Cartoni, Antonella ^a   Menna, Pierantonio ^b   Salvatorelli, Emanuela ^b   Braghiroli, Daniela ^b   Giampietro, Rossella ^b   Animati, Fabio ^a   Urbani, Andrea ^b   Del Boccio, Piero ^b   Minotti, Giorgio ^b,c  

^a Menarini Ricerche ^*  (Italy)

^b UNIVERSITY OF CHIETI   (Italy)

^c School of Medicine   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACIDS; CHROMOPHORES; MASS SPECTROMETRY; OXIDATION; TOXICITY; TUMORS;

CARDIOTOXICITY; OXIDATIVE DEGRADATION;

DEGRADATION;

3 METHOXYPHTHALIC ACID; ANTHRACYCLINE DERIVATIVE; DAUNORUBICIN; DOXORUBICIN; FERRYLMYOGLOBIN; HEMIN; HYDROGEN PEROXIDE; IDARUBICIN; NAPHTHAZARIN; PHTHALIC ACID DERIVATIVE; PORPHYRIN DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ARTICLE; CARDIOTOXICITY; CHEMICAL REACTION KINETICS; CHROMATOPHORE; DRUG DEGRADATION; DRUG OXIDATION; EMBRYO; ENZYME ACTIVITY; HEART MUSCLE CELL; HUMAN; HUMAN TISSUE; MOUSE; NONHUMAN; PRIORITY JOURNAL; PROTEIN FUNCTION; RAT; STOICHIOMETRY; ULTRAVIOLET RADIATION;

ANIMALS; ANTHRACYCLINES; ANTIBIOTICS, ANTINEOPLASTIC; ANTINEOPLASTIC AGENTS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYTOSOL; DOXORUBICIN; HORSES; HUMANS; HYDROGEN PEROXIDE; IRON; KINETICS; MALE; METMYOGLOBIN; MICE; MICE, INBRED BALB C; MODELS, CHEMICAL; MYOCARDIUM; MYOGLOBIN; OXYGEN; PHTHALIC ACIDS; PORPHYRINS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPECTROPHOTOMETRY; TIME FACTORS; ULTRAVIOLET RAYS;

ANIMALIA; EQUUS CABALLUS; MURINAE;

EID: 1242272119     PISSN: 00219258     EISSN: None     Source Type: Journal    
DOI: 10.1074/jbc.M306568200     Document Type: Article

References (41)

1. Yusa, K., and Shikama, K. (1987) Biochemistry 26, 6684-6688
2. Galaris, D., and Korantzopoulos, P. (1997) Free Radic. Biol. Med. 22, 657-667
3. Arduini, A., Eddy, L., and Hochstein, P. (1990) Free Radic. Biol. Med. 9, 511-513
4. Gunther, M. R., Sampath, V., and Caughey, W. S. (1999) Free Radic. Biol. Med. 26, 1388-1395
5. Egawa, T., Shimada, H., and Ishimura, Y. (2000) J. Biol. Chem. 275, 34858-34866
6. Rao, S. I., Wilks, A., Hamberg, M., and Ortiz de Montellano, P. R. (1994) J. Biol. Chem. 269, 7210-7216
7. DeGray, J. A., Gunther, M. R., Tschirret-Guth, R., Ortiz de Montellano, P. R., and Mason, R. P. (1997) J. Biol. Chem. 272, 2359-2362
8. Gunther, M. R., Sturgeon, B. E., and Mason, R. P. (2000) Free Radic. Biol. Med. 28, 709-719
9. Doroshow, J. H., and Davies, K. J. (1986) J. Biol. Chem. 261, 3068-3074
10. Minotti, G., Cairo, G., and Monti, E. (1999) FASEB J. 13, 199-212
11. Kalyanaraman, B., Joseph, J., Kalivendi, S., Wang, S., Konorev, E., and Kotamraju, S. (2002) Mol. Cell. Biochem. 234, 119-124
12. Trost, L. C., and Wallace, K. B. (1994) Biochem. Biophys. Res. Commun. 204, 30-37
13. Taylor, D., and Hochstein, P. (1978) Biochem. Pharmacol. 27, 2079-2082
14. Menna, P., Salvatorelli, E., Giampietro, R., Liberi, G., Teodori, G., Calafiore, A. M., and Minotti, G. (2002) Chem. Res. Toxicol. 15, 1179-1189
15. Miura, T., Muraoka, S., and Fujimoto, Y. (2000) Biochem. Pharmacol. 60, 95-99
16. Reszka, K. J., McCormick, M. L., and Britigan, B. E. (2001) Biochemistry 40, 15349-15361
17. Reszka, K. J., McCormick, M. L., and Britigan, B. E. (2003) Free Radic. Biol. Med. 35, 78-93
18. Reszka, K. J., and Britigan, L. H. (2002) Free Radic. Biol. Med. 33, (suppl.) 443
19. Wentzel, B. B., Donners, M. P. J., Alsters, P. L., Feiters, M. C., and Nolte, R. J. M. (2000) Tetrahedron 56, 7797-7803
20. Mordente, A., Santini, S., Miggiano, G. A. D., Martorana, G. E., Petitti, T., Minotti, G., and Giardina, B. (1994) J. Biol. Chem. 269, 27394-27400
21. Taatjes, D. J., Gaudiano, G., Resing, K., and Koch, T. H. (1997) J. Med. Chem. 40, 1276-1286
22. Minotti, G., Saponiero, A., Licata, S., Menna, P., Calafiore, A. M., Teodori, G., and Gianni, L. (2001) Clin. Cancer Res. 7, 1511-1515
23. Minotti, G., Cavaliere, A. F., Mordente, A., Rossi, M., Schiavello, R., Zamparelli, R., and Possati, G. F. (1995) J. Clin. Investig. 95, 1595-1605
24. Swaanenburg, J. C., Visser-VanBrummen, P. J., DeJongste, M. J., and Tiebosch, A. T. (2001) Am. J. Clin. Pathol. 115, 770-777
25. Minotti, G., Ronchi, R., Salvatorelli, E., Menna, P., and Cairo, G. (2001) Cancer Res. 61, 8422-8428
26. Mosmann, T. (1983) J. Immunol. Methods 65, 55-63
27. Stoscheck, C. M. (1990) Methods Enzymol. 182, 50-68
28. Van der Zee, J., Barr, D. P., and Mason, R. P. (1996) Free Radic. Biol. Med. 20, 199-206
29. Bloom, J., Lehman, P., Israel, M., Rosario, O., and Korfmacher, W. A. (1992) J. Anal. Toxicol. 16, 223-227
30. Arcamone, F., Cassinelli, G., Franceschi, G., Penco, S., Pol, C., Redaelli, S., and Selva, A. (1972) International Symposium on Adriamycin, pp. 10-22, Springer-Verlag, Berlin
31. Šantavý, F., Hruban, L., Šimánek, V., and Walterová, D. (1970) Collect. Czech. Chem. Commun. 35, 2418-2443
32. Giulivi, C., and Cadenas, E. (1998) Free Radic. Biol. Med. 24, 269-279
33. Baron, C. P., Skibsted, L. H., and Andersen, H. J. (2000) Free Radic. Biol. Med. 28, 549-558
34. Gianni, L., Vigano, L., Locatelli, A., Capri, G., Giani, A., Tarenzi, E., and Bonadonna, G. (1997) J. Clin. Oncol. 15, 1906-1915
35. Alexander, J., Bhatia, A. V., Mitscher, L. A., Omoto, S., and Suzuki, T. (1980) J. Org. Chem. 45, 20-24
36. Ramu, A., Mehta, M. M., Liu, J., Turyan, I., and Aleksic, A. (2000) Cancer Chemother. Pharmacol. 46, 449-458
37. Schmidt, H. W., Haemmerli, S. D., Schoemaker, H. E., and Leisola, M. S. A. (1989) Biochemistry 28, 1776-1783
38. Akman, S. A., Forrest, G., Chu, F. F., Esworthy, R. S., and Doroshow, J. H. (1990) Cancer Res. 50, 1397-1402
39. Gille, L., and Nohl, H. (1997) Free Radic. Biol. Med. 23, 775-782
40. Alberts, D. S., Bachur, N. R., and Holtzman, J. L. (1971) Clin. Pharmacol. Ther. 12, 96-104
41. Arcamone, F., Lazzati, M., Vicario, G. P., and Zini, G. (1984) Cancer Chemother. Pharmacol. 12, 157-166