The secondary alcohol and aglycone metabolites of doxurubicin alter metabolism of human erythrocytes

Brazilian Journal of Medical and Biological Research

Volumn 36, Issue 12, 2003, Pages 1643-1651

  Misiti, F ^a   Giardina, B ^a,b   Mordente, A ^a   Clementi, M E ^b  

^a CATHOLIC UNIVERSITY   (Italy)

^b CNRS   (France)

Author keywords

Aglycone metabolite; Anthracyclines; Doxorubicin; Doxorubicinol; Hemoglobin; Pentose phosphate pathway; 13C NMR spectroscopy

Indexed keywords

ADRIAMYCINONE; ALCOHOL DERIVATIVE; ANTIOXIDANT; CATALASE; DOXORUBICIN; DOXORUBICIN DERIVATIVE; DOXORUBICINOL; DRUG METABOLITE; GLUTATHIONE PEROXIDASE; GLUTATHIONE REDUCTASE; HEMOGLOBIN; METHEMOGLOBIN; OXYGEN; PENTOSE PHOSPHATE; SUPEROXIDE DISMUTASE;

ARTICLE; BIOLOGICAL MODEL; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG EXPOSURE; DRUG PROTEIN BINDING; DRUG STRUCTURE; ENZYME ACTIVITY; ENZYME INHIBITION; ERYTHROCYTE METABOLISM; HUMAN; HUMAN CELL; OXYGEN AFFINITY; PENTOSE PHOSPHATE CYCLE; TEMPERATURE MEASUREMENT;

EID: 0346336127     PISSN: 0100879X     EISSN: 1414431X     Source Type: Journal    
DOI: 10.1590/S0100-879X2003001200005     Document Type: Article

References (37)

1. Singal PK & Iliskovic N (1998). Doxorubicin-induced cardiomyopathy. New England Journal of Medicine, 339: 900-905.
2. Lefrak EA, Pitha J, Rosenheim S & Gottlieb JA (1973). A clinical pathological analysis of adriamycin cardiotoxicity. Cancer, 32: 302-314.
3. Olson RD & Mushlin PS (1990). Doxorubicin cardiotoxicity: analysis of prevailing hypotheses. FASEB Journal, 4: 3076-3086.
4. Powis G (1989). Free radical formation by antitumor quinones. Free Radical Biology and Medicine, 6: 63-101.
5. Singal PK, Deally CMR & Weinberg LE (1987). Subcellular effects of adryamicin in the heart: a concise review. Journal of Molecular and Cellular Cardiology, 19: 817-828.
6. Licata S, Saponiero A, Mordente A & Minotti G (2000). Doxorubicin metabolism and toxicity in human myocardium: Role of cytoplasmic deglycosylation and carbonyl reduction. Chemical Research in Toxicology, 13: 414-420.
7. Boucek Jr RJ, Olson RD, Brenner DE, Ogumbumni ME, Inui M & Flescher S (1987). The major metabolite of doxorubicin is a potent inhibitor of membrane associated ion pumps: a correlative study of cardiac muscle with isolated membrane fractions. Journal of Biological Chemistry, 262: 15851-15856.
8. Olson RD, Mushlin PS, Brenner DE, Fleischer S, Cusack BJ, Chang BK & Boucek Jr RJ (1988). Doxorubicin cardiotoxicity may be caused by its metabolite, doxorubicinol. Proceedings of the National Academy of Sciences, USA, 85: 3585-3589.
9. Sokolove PM, Kester MB & Haynes J (1993). Interaction of adriamycin aglycones with isolated mitochondria. Effect of selenium deficiency. Biochemical Pharmacology, 46: 691-697.
10. 2+ from rat heart mitochondria. Induction by adriamycin aglycone. Biochemical Pharmacology, 37: 803-812.
11. + movements in red blood cells. Research Communications in Chemical Pathology and Pharmacology, 26: 277-284.
12. + antiport in erythrocytes isolated from cancer patients. Cancer Research, 56: 511-514.
13. Thompson MG, Chahwala SB & Hickman JA (1987). Inhibition of human erythrocyte inositol lipid metabolism by adriamycin. Cancer Research, 47: 2799-2803.
14. Miura T, Muraoka S & Ogiso T (1993). Adriamycin-induced lipid peroxidation of erythrocyte membranes in the presence of ferritin and the inhibitory effect of ceruplasmin. Biological and Pharmaceutical Bulletin, 16: 664-667.
15. DeAtley SM, Aksenov MY, Aksenova MV, Carney JM & Butterfield DA (1998). Adriamycin induces protein oxidation in erythrocyte membrane. Pharmacology and Toxicology, 83: 62-68.
16. Suwalsky M, Hernandez P, Villena F, Aguilar F & Sotomayor CP (1999). The anticancer drug adriamycin interacts with the human erythrocyte membrane. Zeithschrift für Naturforschung. Section C, 54c: 271-277.
17. Andersen A, Holte H & Slordal L (1999). Pharmacokinetics and metabolism of doxorubicin after short-term infusions in lymphoma patients. Cancer Chemotherapy and Pharmacology, 44: 422-426.
18. Lachatre F, Marquet P, Ragot S, Gaulier JM, Cardot P & Dupuy JL (2000). Simultaneous determination of four anthracyclines and three metabolites in human serum by liquid chromatography-electrospray mass spectrometry. Journal of Chromatography. B, Biomedical Applications, 738: 281-291.
19. Takanashi S & Bachur NR (1976). Adriamycin metabolism in man. Evidence from urinary metabolism. Drug Metabolism and Disposition, 4: 79-87.
20. Zijlstra WG, Buursma A & Meeuwsen-van der Roast WP (1991). Absorption spectra of human fetal and adult oxyhemoglobin, deoxyhemoglobin, carboxyhemoglobin, and methemoglobin. Clinical Chemistry, 37: 1633-1638.
21. 2-dependent stimulation of the pentose phosphate pathway by S-nitrosocysteine in human erythrocytes. Biochemical and Biophysical Research Communications, 294: 829-834.
22. Messana I, Ferroni F, Misiti F, Girelli G, Pupella M, Castagnola M, Zappacosta B & Giardina B (2000). Blood bank conditions and RBCs: the progressive loss of metabolic modulation. Transfusion, 40: 353-360.
23. Beutler E (1975) Red cell metabolism. In: Beutler E (Editor), A Manual of Biochemical Methods. 2nd edn. Grune & Stratton, New York, 71-73.
24. Heikkila RE (1985). Autoxidation of 6-hydroxydopamine. In: Greenwald RA (Editor), Handbook of Methods for Oxygen Radicals Research. CRC Press, Boca Raton, FL, USA, 233-235.
25. Carlberg I & Mannervik B (1985). Glutathione reductase. Methods in Enzymology, 113: 484-490.
26. Giardina B & Amiconi G (1981). Measurement of binding of gaseous and non gaseous ligands to hemoglobins by conventional spectrophotometric procedures. Methods in Enzymology, 76: 417-427.
27. Boyer PD (1954). Spectrophotometric study of the reaction of protein sulfhydryl groups with organic mercurials. Journal of the American Chemical Society, 76: 4331-4337.
28. Henderson CA, Metz EN, Balcerzak SP & Sagone Jr AL (1978). Adriamycin and daunomycin generate reactive oxygen compounds in erythrocytes. Blood, 52: 878-885.
29. Bates DA & Winterbourn CC (1982). Reaction of adriamycin with haemoglobin. Superoxide dismutase indirectly inhibits reactions of the adriamycin semiquinone. Biochemical Journal, 203: 155-160.
30. Minotti G, Recalcati S, Mordente A, Liberi G, Calafiore AM, Mancuso C, Preziosi P & Cairo G (1998). The secondary alcohol metabolite of doxorubicin irreversibly inactivates aconitase/iron regulatory protein-1 in cytosolic fractions from human myocardium. FASEB Journal, 12: 541-552.
31. McMillan DC, Jensen CB & Jollow DJ (1998). Role of lipid peroxidation in dapsone-induced hemolytic anemia. Journal of Pharmacology and Experimental Therapeutics, 287: 868-876.
32. 2 equilibrium of normal and SH(beta 93)-modified human hemoglobin. European Journal of Biochemistry, 121: 325-328.
33. Ramanathan-Girish S & Boroujerdi M (2001). Contradistinction between doxorubicin and epirubicin: in vitro interaction with blood components. Journal of Pharmacy and Pharmacology, 53: 15-21.
34. Vaidyanathan S & Boroujerdi M (2000). Interaction of dexrazoxane with red blood cells and hemoglobin alters pharmacokinetics of doxorubicin. Cancer Chemotherapy and Pharmacology, 46: 93-100.
35. Shinohara K & Tanaka KR (1980). The effects of adriamycin (doxorubicin HCl) on human red blood cells. Hemoglobin, 4: 735-745.
36. Miccadei S, Fanciulli M, Bruno T, Paggi MG & Floridi A (1996). Energy metabolism of adryamicin-sensitive and resistant Ehrlich ascites tumor cells. Oncology Research, 8: 27-35.
37. Ferretti A, Chen LL, Di Vito M, Barca S, Tombesi M, Cianfriglia M, Bozzi A, Strom R & Podo F (1993). Pentose phosphate pathway alterations in multi drug resistant leukemic T-cells: 31P NMR and enzymatic studies. Anticancer Research, 13: 867-872.