Metabolic activation of adriamycin by NADPH-cytochrome P450 reductase; overview of its biological and biochemical effects

Acta Biochimica Polonica

Volumn 49, Issue 2, 2002, Pages 323-331

  Bartoszek, Agnieszka ^a  

^a GDANSK UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

Adriamycin; Covalent binding to macromolecules; NADPH cytochrome P450 reductase; Oxygen radicals

Indexed keywords

LETHRINIDAE;

ANTINEOPLASTIC AGENT; ANTINEOPLASTIC ANTIBIOTIC; DOXORUBICIN; MALONALDEHYDE; NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE FERRIHEMOPROTEIN REDUCTASE; SCAVENGER;

ANIMAL; ARTICLE; BREAST TUMOR; CELL CULTURE; CHEMISTRY; DNA ADDUCT; ENZYMOLOGY; HUMAN; LIVER; METABOLISM; RAT;

ANIMALS; ANTIBIOTICS, ANTINEOPLASTIC; ANTINEOPLASTIC AGENTS; BREAST NEOPLASMS; DNA ADDUCTS; DOXORUBICIN; FREE RADICAL SCAVENGERS; HUMANS; LIVER; MALONDIALDEHYDE; NADP; NADPH-FERRIHEMOPROTEIN REDUCTASE; RATS; TUMOR CELLS, CULTURED;

EID: 0039483056     PISSN: 0001527X     EISSN: None     Source Type: Journal    
DOI: 10.18388/abp.2002_3790     Document Type: Article

References (21)

1. Alegria AA, Samuni A, Mitchell JB, Riesz P, Russo A. (1989) Free radicals induced by adriamycin-sensitive and adriamycin-resistant cells: a spin-trapping study. Biochemistry.; 28: 8653-8.
2. Bachur NS, Gordon SL, Gee MV, Kon H. (1979) NADPH cytochrome P450 reductase activation of anticancer agents to free radicals. Proc Natkl Acad Sci U S A.; 76: 954-7.
3. Bartoszek A, Wolf CR. (1992) Enhancement of doxorubicin toxicity following activation by NADPH cytochrome P450 reductase. Biochem Pharmacol.; 43: 1449-57.
4. Bligh HFJ, Bartoszek A, Robson CN, Hickson ID, Kasper CB, Beggs JD, Wolf CR. (1990) Activation of mitomycin C by NADPH: cytochrome P450 reductase. Cancer Res.; 50: 7789-92.
5. Cummings J, Allan L, Willmott N, Riley R, Workman P, Smyth JF. (1994) The enzymology of doxorubicin quinone reduction in tumour tissue. Biochem Pharmacol.; 44: 2175-83.
6. Cummings J, Bartoszek A, Smyth JF. (1991) Determination of covalent binding to intact DNA, RNA, and oligonucleotides by intercalating anticancer drugs using high-performance liquid chromatography. Studies with doxorubicin and cytochrome P450 reductase. Anal Biochem.; 194: 146-55.
7. Doroshow JH. (1986) Prevention of doxorubicin-induced killing of MCF-7 human breast cells by oxygen radical scavengers and iron chelating agents. Biochem Biophys Res Commun.; 135: 330-5.
8. Gaudiano G, Koch TH, Lo Bello M, Nuccetelli M, Ravagnan G, Serafino A, Sinibaldi-Vallebona P. (2000) Lack of glutathione conjugation to adriamycin in human breast cancer MCF-7/DOX cells. Biochem Pharmacol.; 60: 1915-23.
9. Gerwitz DA. (1999) A critical evaluation of the mechanism of action proposed for the antitumor effects of the anthracycline antibiotics adriamycin and daunomycin. Biochem Pharmacol.; 57: 724-41.
10. Konopa J. (1990) Interstrand DNA crosslinking by 1-nitroacridines, anthracyclines and aminoanthraquinones. Pharmacol Ther.; 7 (suppl.): 83-94.
11. Paur E, Youngman RJ, Lengfelder E, Elstner EF. (1984) Mechanism of adriamycin-dependent oxygen activation catalyzed by NADPH-cytochrome c-(ferrodoxin)-oxido-reductase. Z Naturforsch.; 39c: 261-7.
12. Podell ER, Harrington DJ, Taatjes DJ, Koch TH. (1999) Crystal structure of epidoxorubicin-formaldehyde virtual crosslink of DNA and evidence for its formation in human breast-cancer cells. Acta Cryst.; D55: 1516-23.
13. Sharples RA, Cullinane C, Phillips DR. (2000) Adriamycin-induced inhibition of mitochondrial-encoded polypeptides as a model system for the identification of hotspots for DNA-damaging agents. Anti-Cancer Drug Design.; 15: 183-90.
14. Sinha BK. (1989) Free radicals in anticancer drug pharmacology Chem-Biol Interact.; 69: 293-317.
15. Składanowski A, Konopa J. (1994) Relevance of interstrand DNA crosslinking induced by anthracyclines for their biological activity. Biochem Pharmacol.; 47: 2279-87.
16. Taatjes DJ, Fenick DJ, Gaudiano G, Koch TH. (1998) A redox pathway leading to the alkylation of nucleic acids by doxorubicin and related anthracyclines: application to the design of antitumor drugs for resistant cancer. Curr Pharmaceut Design.; 4: 203-18.
17. Taatjes DJ, Koch TH. (2001) Nuclear targeting and retention of anthracycline antitumor drugs in sensitive and resistant tumor cells. Curr Med Chem.; 8: 15-29.
18. Tempczyk A, Tarasiuk J, Ossowski T, Borowski E. (1988) An alternative concept for the molecular nature of the peroxidating ability of anthracycline antitumor antibiotics and anthracenediones. Anti-Cancer Drug Design.; 2: 371-85.
19. Tolba KA, Deliargyris EN. (1999) Cardiotoxicity of cancer therapy. Cancer Invest.; 17: 408-22.
20. Wallace KB, Johnson AJ. (1987) Oxygen-dependent effect of microsomes on the binding of doxorubicin to rat hepatic nuclear DNA. Mol Pharmacol.; 31: 307-11.
21. Zeman SM, Phillips DR, Crothers DM. (1998) Characterization of covalent adriamycin-DNA adducts. Proc Natl Acad Sci U S A.; 95: 11561-5.