Thiol oxidation induced by oxidative action of adriamycin

Free Radical Research

Volumn 38, Issue 9, 2004, Pages 963-968

  Muraoka, Sanae ^a   Miura, Toshiaki ^a  

^a HOKKAIDO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Adriamycin; Anthracycline; Glutathione; Horseradish peroxidase; Quinone; Semiquinone

Indexed keywords

ANTHRACYCLINE; CREATINE KINASE; DOXORUBICIN; FREE RADICAL; GLUTATHIONE; HORSERADISH PEROXIDASE; HYDROQUINONE; HYPOXANTHINE; SEMIQUINONE; THIOL; XANTHINE OXIDASE;

ANAEROBIC CAPACITY; ARTICLE; CARDIOTOXICITY; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; DRUG STRUCTURE; ELECTRON SPIN RESONANCE; ENZYME INACTIVATION; LIPID OXIDATION; OXIDATION; STRUCTURE ANALYSIS;

ACLARUBICIN; ANTIBIOTICS, ANTINEOPLASTIC; BENZOQUINONES; CREATINE KINASE; DAUNORUBICIN; DOXORUBICIN; ELECTRON SPIN RESONANCE SPECTROSCOPY; EPIRUBICIN; FREE RADICALS; GLUTATHIONE; HORSERADISH PEROXIDASE; HYDROGEN PEROXIDE; HYPOXANTHINE; IDARUBICIN; OXIDATION-REDUCTION; SULFHYDRYL COMPOUNDS; XANTHINE OXIDASE;

ARMORACIA RUSTICANA;

EID: 5044241619     PISSN: 10715762     EISSN: None     Source Type: Journal    
DOI: 10.1080/10715760400000919     Document Type: Article

References (35)

1. Platel, D., Pouna, P., Bonoron-Adele, S. and Robert, J. (1999) "Comparative cardiotoxicity of idarubicin and doxorubicin. using the isolated perfused rat heart model", Anticancer Drugs 10, 671-676.
2. Hirano, S., Wakazono, K., Agata, N. and Iguchi, H. (1994) "Comparison of cardiotoxicity of pirarubicin, epirubicin and doxorubicin in the rat", Drugs Exp. Clin. Res. 20, 153-160.
3. Temma, K., Akera, T., Chugun, A., Kondo, H., Hagane, K. and Hirano, S. (1993) "Comparison of cardiac actions of doxorubicin, pirarubicin and aclarubicin in isolated guinea-pig heart", Eur. J. Pharmacol. 234, 173-181.
4. Lenaz, L. and Page, J. (1976) "Cardiotoxicity of adriamycin related anthracyclines", Cancer Treat. Rev. 3, 111-120.
5. Singal, P.K., Iliskovic, N., Li, T. and Kumar, D. (1997) "Adriamycin cardiomyopathy: pathophysiology and prevention", FASEB J. 11, 931-936.
6. Doroshow, J.H. and Davies, K.J. (1986) "Redox cycling of anthracyclines by cardiac mitochondria. II. Formation of superoxide anion, hydrogen peroxide, and hydroxyl radical", J. Biol. Chem. 261, 3068-3074.
7. Davies, K.J. and Doroshow, J.H. (1986) "Redox cycling of anthracyclines by cardiac mitochondria. I. Anthracycline radical formation by NADH dehydrogenase", J. Biol. Chem. 261, 3060-3067.
8. Thornalley, P.J. and Dodd, N.J. (1985) "Free radical production from normal and adriamycin-treated rat cardiac sarcosomes", Biochem. Pharmacol. 34, 669-674.
9. Mimnaugh, E.G., Trush, M.A., Bhatnagar, M. and Gram, T.E. (1985) "Enhancement of reactive oxygen-dependent mitochondrial membrane lipid peroxidation by the anticancer drug adriamycin", Biochem. Pharmacol. 34, 847-856.
10. Muraoka, S. and Miura, T. (2003) "Inactivation of mitochondrial succinate dehydrogenase by adriamycin activated horseradish peroxidase and hydrogen peroxide", Chem. Biol. Interact. 145, 67-75.
11. Watts, D.C. (1973) "Creatine Kinase", In: Boyer, P.D., ed., The enzymes VII (Academic Press, New York and London), pp 383-455.
12. Mohamed, H.E., El-Swefy, S.E. and Hagar, H.H. (2000) "The protective effect of glutathione administration on adriamycin-induced acute cardiac toxicity in rats", Pharmacol. Res. 42, 115-121.
13. Olson, R.D., MacDonald, J.S., vanBoxtel, C.J., Boerth, R.C., Harbison, R.D., Slonim, A.E., Freeman, R.W. and Oates, J.A. (1980) "Regulatory role of glutathione and soluble sulfhydryl groups in the toxicity of adriamycin", J. Pharmacol. Exp. Ther. 215, 450-454.
14. Miura, T., Muraoka, S. and Fujimoto, Y. (2000) "Inactivation of creatine kinase by adriamycin during interaction with horseradish peroxidase", Biochem. Pharmacol. 60, 95-99.
15. El-Missiry, M.A., Othman, A.I., Amer, M.A. and Abd, El-Aziz, M.A. (2001) "Attenuation of the acute adriamycin-induced cardiac and hepatic oxidative toxicity by N-(2-mercaptopropionyl) glycine in rats", Free Radic. Res. 35, 575-581.
16. Abd, El-Aziz, M.A., Othman, A.I., Amer, M. and El-Missiry, M.A. (2001) "Potential protective role of angiotensin-converting enzyme inhibitors captopril and enalapril against adriamycin-induced acute cardiac and hepatic toxicity in rats", J. Appl. Toxicol. 21, 469-473.
17. Das, D. and Banerjee, R.K. (1993) "Effect of stress on the antioxidant enzymes and gastric ulceration", Mol. Cell. Biochem. 125, 115-125.
18. Redinbaugh, M.G. and Turley, R.B. (1986) "Adaptation of the bicinchoninic acid protein assay for use with microtiter plates and sucrose gradient fraction", Anal. Biochem. 153, 267-271.
19. Ellman, G.L. (1959) "Tissue sulfhydryl groups", Arch. Biochem. Biophys. 82, 70-77.
20. Beckman, J.S. and Siedow, J.N. (1985) "Bactericidal agents generated by the peroxidase-catalyzed oxidation of parahydroquinones", J. Biol. Chem. 260, 14604-14609.
21. Ross, D., Albano, E., Nilsson, U. and Moldeus, P. (1984) "Thiyl radicals-formation during peroxidase-catalyzed metabolism of acetaminophen in the presence of thiols", Biochem. Biophys. Res. Commun. 125, 109-115.
22. Pan, S.S. and Bachur, N.R. (1980) "Xanthine oxidase catalyzed reductive cleavage of anthracycline antibiotics and free radical formation", Mol. Pharmacol. 17, 95-99.
23. Mottley, C., Toy, K. and Mason, R.P. (1987) "Oxidation of thiol drugs and biochemicals by the lactoperoxidase/hydrogen peroxide system", Mol. Pharmacol. 31, 417-421.
24. Metodiewa, D., Reszka, K. and Dunford, H.B. (1989) "Oxidation of the substituted catechols dihydroxyphenylalanine methyl ester and trihydroxyphenylalanine by lactoperoxidase and its compounds", Arch. Biochem. Biophys. 274, 601-608.
25. Metodiewa, D. and Dunford, H.B. (1990) "Evidence for one-electron oxidation of benzylpenicillin G by lactoperoxidase compounds I and II", Biochem. Biophys. Res. Commun. 169, 1211-1216.
26. Rota, C., Fann, Y.C. and Mason, R.P. (1999) "Phenoxyl free radical formation during the oxidation of the fluorescent dye 2′,7′-dichlorofluorescein by horseradish peroxidase. Possible consequences for oxidative stress measurements", J. Biol. Chem. 274, 28161-28168.
27. Muraoka, S. and Miura, T. (2003) "Inactivation of creatine kinase during the interaction of mefenamic acid with horseradish peroxidase and hydrogen peroxide: participation by the mefenamic acid radical", Life Sci. 72, 1897-1907.
28. Mimnaugh, E.G., Kennedy, K.A., Trush, M.A. and Sinha, B.K. (1985) "Adriamycin-enhanced membrane lipid peroxidation in isolated rat nuclei", Cancer Res. 45, 3296-3304.
29. Minotti, G. (1990) "NADPH- and adriamycin-dependent microsomal release of iron and lipid peroxidation", Arch. Biochem. Biophys. 277, 268-276.
30. 3+-induced inactivation of rat heart mitochondrial creatine kinase: sensitivity to lipid peroxidation", Biol. Pharm. Bull. 17, 1220-1223.
31. Demant, E.J. and Jensen, P.K. (1983) "Destruction of phospholipids and respiratory-chain activity in pig-heart submitochondrial particles induced by an adriamycin-iron complex", Eur. J. Biochem. 132, 551-556.
32. Miura, T., Muraoka, S. and Ogiso, T. (1993) "Adriamycin-induced lipid peroxidation of erythrocyte membranes in the presence of ferritin and the inhibitory effect of ceruloplasmin" , Biol. Pharm. Bull. 16, 664-667.
33. 3+", Pharmacol. Toxicol. 69, 296-300.
34. Rothig, H.J., Kraemer, H.P. and Sedlacek, H.H. (1985) "Aclarubicin: experimental and clinical experience", Drugs Exp. Clin. Res. 11, 123-125.
35. Vile, G. and Winterbourn, C. (1990) "Thiol oxidation and inhibition of Ca-ATPase by adriamycin in rabbit heart microsomes", Biochem. Pharmacol. 39, 769-774.