Differential Ability of Cytostatics from Anthraquinone Group to Generate Free Radicals in Three Enzymatic Systems: NADH Dehydrogenase, NADPH Cytochrome P450 Reductase, and Xanthine Oxidase

Oncology Research

Volumn 13, Issue 5, 2002, Pages 245-252

  Pawłowska, Jolanta ^a   Tarasiuk, Jolanta ^a,c   Wolf, C Roland ^b   Paine, Mark J I ^b   Borowski, Edward ^a  

^a GDANSK UNIVERSITY OF TECHNOLOGY   (Poland)

^b UNIVERSITY OF DUNDEE   (United Kingdom)

^c UNIVERSITY OF SZCZECIN   (Poland)

Author keywords

Anthraquinone compounds; Free radical formation; NADH dehydrogenase; NADPH cytochrome P450 reductase; Xanthine oxidase

Indexed keywords

2 (DIMETHYLAMINOETHYLAMINO)PYRIDAZONANTHRONE; 2 [2 (DIMETHYLAMINO)ETHYL] 6 [2 (DIMETHYLAMINO)ETHYLAMINO]PYRIMIDO[5,6,1 DE]ACRIDINO 1,3,7 TRIONE; 3' HYDROXYDOXORUBICIN; 5 IMINODAUNORUBICIN; ANNAMYCIN; ANTHRAPYRIDAZONE; ANTHRAQUINONE DERIVATIVE; CYTOSTATIC AGENT; DAUNORUBICIN; DAUNORUBICIN DERIVATIVE; DOXORUBICIN DERIVATIVE; EPIRUBICIN; FREE RADICAL; MITOXANTRONE; N (1 CARBOXYPROPEN 1 YL)DAUNORUBICIN; N,N DIBENZYLDAUNORUBICIN; OXYGEN; PA 39; PYRIMIDOACRIDONE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE DEHYDROGENASE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE FERRIHEMOPROTEIN REDUCTASE; UNCLASSIFIED DRUG; XANTHINE OXIDASE; ANTINEOPLASTIC AGENT; REACTIVE OXYGEN METABOLITE;

ANTINEOPLASTIC ACTIVITY; ARTICLE; ATMOSPHERE; CARDIOTOXICITY; CATALYSIS; CYTOTOXICITY; DRUG EFFECT; DRUG STRUCTURE; DRUG SYNTHESIS; ELECTRON TRANSPORT; PRIORITY JOURNAL; STRUCTURE ANALYSIS; ANIMAL; CHEMISTRY; DRUG POTENTIATION; HORSE; METABOLISM; SWINE;

ANIMALS; ANTHRAQUINONES; ANTINEOPLASTIC AGENTS; FREE RADICALS; HORSES; NADH DEHYDROGENASE; NADPH-FERRIHEMOPROTEIN REDUCTASE; REACTIVE OXYGEN SPECIES; SWINE; XANTHINE OXIDASE;

EID: 0141889541     PISSN: 09650407     EISSN: None     Source Type: Journal    
DOI: 10.3727/096504003108748294     Document Type: Article

References (55)

1. Wiernik, P. H.; Dutcher, J. P. Clinical importance of anthracyclines in the treatment of acute myeloid leukemia. Leukemia 6(Suppl. 1):67; 1992.
2. Lown, J. W. Discovery and development of anthracycline antitumor antibiotics. Chem. Soc. Rev. 165; 1993.
3. Olson, R. D.; Mushlin, P. S. Doxorubicin cardiotoxicity: Analysis of prevailing hypothesis. FASEB J. 4:3076; 1990.
4. Havlin, K. A. Cardiotoxicity of anthracyclines and other antineoplastic agents. In: Acosta, D., ed. Cardiovascular toxicology (2nd ed.). New York: Raven Press; 1992:143.
5. Rhoden, W.; Hasleton, P.; Brooks, N. Anthracyclines and the heart. Br. Heart J. 70:499; 1993.
6. Bachur, N. E.; Gordon, S. L.; Gee, M. V. Anthracycline antibiotic augmentation of microsomal electron transport and free radical formation. Mol. Pharmacol. 13:901; 1977.
7. Bachur, N R.; Gordon, S. L.; Gee, M. V. A general mechanisms for microsomal activation of quinone anticancer agents. Cancer Res. 38:1745; 1978.
8. Doroshow, I.; Reeves, J. Daunorubicin stimulated reactive oxygen metabolism in cardiac sarcosomes. Biochem. Pharmacol. 26:285; 1981.
9. Powis, G. Free radical formation by antitumour quinones. Free Radic. Biol. Med. 6:63; 1989.
10. O'Brien, P. J. Molecular mechanisms of quinone cytotoxicity. Chem. Biol. Interact. 80:1; 1991.
11. Begleiter, A. Cytocidal action of the quinine group and its relationship to antitumor activity. Cancer Res. 43:481; 1983.
12. Begleiter, A. Studies on the mechanism of action of quinine antitumor agents. Biochem. Pharmacol. 34:2629; 1985.
13. Begleiter, A.; Blair, G. W. Quinone-induced DNA damage and its relationship to antitumor activity in L5178Y lymphoblasts. Cancer Res. 44:78; 1984.
14. Begleiter, A.; Leith, M. K. Activity of quinine alkylating agents in quinine resistant cells. Cancer Res. 50:2872; 1990.
15. Doroshow, J. H. Effect of anthracycline antibiotics on oxygen radical formation in rat heart. Cancer Res. 43:460; 1983.
16. Shinha, B. K. Free radicals in anticancer drug pharmacology. Chem. Biol. Interact. 69:293; 1989.
17. Davies, K. J. A.; Doroshow, J. H. Redox cycling of anthracyclines by cardiac mitochondria. I. Anthracycline radical formation by NADH dehydrogenase. J. Biol. Chem. 261:3060; 1986.
18. Myers, C. E.; Mcguire, W. P.; Liss, R. H.; Ifrim, I.; Grotzinger, K.; Young, R. C. Adriamycin: The role of lipid peroxidation in cardiac toxicity and tumor response. Science 196:165; 1977.
19. Lee, V.; Randhawa, A. K.; Singal, P. K. Adriamycin-induced myocardial dysfunction in vitro is mediated by free radicals. Am. J. Physiol. 261:H989; 1991.
20. Doroshow, J. H.; Davies, K. J. A. Redox cycling of anthracycline by cardiac mitochondria. II. Formation of superoxide anion, hydrogen peroxide and hydroxyl radical. J. Biol. Chem. 261:3068; 1986.
21. Julicher, R. H. M.; Sterrenberg, L.; Bast, A.; Riksen, K. O. W. M.; Koomen, J. M.; Noordhoek, J. The role of lipid peroxidation in acute doxorubicin-induced cardiotoxicity as studied in rat isolated heart. J. Pharm. Pharmacol. 38:277; 1986.
22. Gille, L.; Nohl, H. Analyses of the molecular mechanism of adriamycin-induced cardiotoxicity. Free Radic. Biol. Med. 23:775; 1997.
23. Davies, K. J. A.; Doroshow, J. H.; Hochstein, P. Mitochondrial NADH dehydrogenase-catalyzed oxygen radical production by adriamycin and the relative inactivity of 5-iminodaunorubicin. FEBS Lett. 153:227; 1983.
24. Doroshow, J. H. Anthracycline antibiotic-stimulated superoxide, hydrogen peroxide and hydroxyl radical production by NADH dehydrogenase. Cancer Res. 43:4543; 1983.
25. Kharasch, E. D.; Novak, R. F. (1983) Bis (alkylamino) anthracenedione antineoplastic agent metabolic activation by NADPH-cytochrome P-450 reductase and NADH dehydrogenase: Diminished activity relative to anthracyclines. Arch. Biochem. Biophys. 224:682; 1983.
26. Pan, S. S.; Bachur, N. R. Xanthine oxidase catalysed reductive cleavage of anthracycline antibiotics and free radical formation. Mol. Pharmacol. 17:95; 1980.
27. Bakker, P. T.; Albracht, S. P. Evidence for two independent pathways of electron transfer in mitochondrial NADH:Q oxidoreductase. I. Pre-steady-state kinetics with NADPH. Biochim. Biophys. Acta 850:413; 1986.
28. Albracht, S. P.; Bakker, P. T. Evidence for two independent pathways of electron transfer in mitochondrial NADH:Q oxidoreductase. II. Kinetics of reoxidation of the reduced enzyme. Biochim. Biophys. Acta 850:423; 1986.
29. Iyanagi, I.; Mason, H. S. Some properties of hepatic reduced nicotinamide adenine dinucleotide phosphate-cytochrome c reductase. Biochemistry 12:2297; 1973.
30. Vermilion, J. L.; Coon, M. J. Highly purified detergent-solubilized NADPH-cytochrome P450 reductase from phenobarbital-induced rat liver microsomes. Biochem. Biophys. Res. Commun. 60:1315; 1974.
31. Schwab, G. E.; Johnson, E. F. In: Guengnerich, F. P., ed. Mammalian cytochromes P450 (Vol. 1). Boca Raton, FL: CRC Press; 1987:55-105.
32. Eger, B. T.; Eikmanns, V.; Pai, E. F.; Sato, M.; Okamoto, K.; Nishino, T. Crystallization and preliminary X-ray diffraction of xanthine oxidase isolated from bovine milk. In: Yagi, K., ed. Flavins and flavoproteins. Berlin: de Gruyter; 1994:727-729.
33. Hart, L. I.; Mcgartoll, M. A.; Chapman, H. R.; Bray, R. C. The composition of milk xanthine oxidase. Biochem. J. 116:851; 1970.
34. Bray, R. C. In: Boyer, D. P., ed. The enzymes (Vol. XII, Part B). New York: Academic Press; 1975:300-419.
35. Huber, R.; Hof, P.; Duarte, R. O.; Moura, J. J. G.; Moura, I.; Liu, M. Y.; Legall, J.; Hille, R.; Archer, M.; Romao, M. J. A structure-based catalytic mechanism for the xanthine oxidase family of molybdenum enzymes. Proc. Natl. Acad. Sci. 93:8846; 1996.
36. Tarasiuk, J.; Tkaczyk-Gobis, K.; Stefanska, B.; Dzieduszycka, M.; Priebe, W.; Martelli, S.; Borowski, E. The role of structural factors of anthraquinone compounds and their quinone-modified analogues in NADH dehydrogenase-catalysed oxygen radical formation. Anticancer Drug Des. 13:923; 1998.
37. Tarasiuk, J.; Garnier-Suillerot, A.; Stefanska, B.; Borowski, E. The essential role of anthraquinones as substrates for NADH dehydrogenase in their redox cycling activity. Anticancer Drug Des. 7:329; 1992.
38. Tarasiuk, J.; Stefanska, B.; Borowski, E. Low stimulation of NADH oxidation and oxygen consumption by 5-iminodaunorubicin and its derivatives. Acta Biochim. Pol. 37: 251; 1990.
39. Frank, P.; Novak, R. F. Effects of anthrapyrazole antineoplastic agents on lipid peroxidation. Biochem. Biophys. Res. Commun. 140:797; 1986.
40. Stefanska, B.; Dzieduszycka, M.; Martelli, S.; Tarasiuk, J.; Bontemps-Gracz, M.; Borowski, E. 6-[Aminoalkykamino]-substituted 7H-benzo[e]perimidin-7-ones as novel antineoplastic agents. Synthesis and biological evaluation. J. Med. Chem. 36:38; 1993.
41. Gams, R. A.; Westler, M. J. Mitoxantrone cardiotoxicity: Results from southeaster cancer study group. Cancer Treat. Symp. 3:31; 1984.
42. Shell, F. C.; Yap, H. Y.; Blumenschein, G.; Valdivieso, M.; Bidey, M. Potential cardiotoxicity with mitoxantrone. Cancer Treat. Rep. 66:1641; 1982.
43. Unverferth, D. V.; Bashore, I. M.; Magrien, R. D.; Fetters, J. K.; Neidhart, J. A. Histology and functional characteristics of human heart after mitoxantrone therapy. Cancer Treat. Symp. 3:47; 1984.
44. Tarasiuk, J.; Tkaczyk, K.; Dzieduszycka, M.; Borowski, E. The structural factors determining the low activity of antitumor anthracenediones, mitoxantrone and ametantrone in free radicals generation. 5th International Symposium on Molecular Aspects of Chemotherapy, Gdansk 21-24 VII; 1995:55.
45. Stefanska, B.; Borowski, E.; Falkowski, L.; Martelli, S. Synthesis and antileukemic activity of some novel N-substituted derivatives of daunorubicin. Pol. J. Chem. 60: 525; 1986.
46. Tong, G. L.; Wu, H. Y.; Smith, T. H.; Henry, D. W. Adriamycin analogues. 3. Synthesis of N-alkylated anthracyclines with enhanced and reduced cardiotoxicity. J. Med. Chem. 22:912; 1979.
47. Tong, G. L.; Henry, D. H.; Acton, E. M. 5-Iminodaunorubicin. Reduced cardiotoxic properties in an antitumor anthracycline. J. Med. Chem. 22:36; 1979.
48. Murdock, K. C.; Child, R. G.; Fabio, P. F.; Angier, R. B.; Wallace, R. E.; Durr, F. E.; Citarella, R. V. Antitumor agents. I. 1,4-bis[(aminoalkyl)amino]-9,10-anthracenediones. J. Med. Chem. 22:1024; 1979.
49. Antonini, J.; Cola, D.; Polucci, P.; Bontemps-Gracz, M.; Borowski, E.; Martelli, S. Synthesis of (dialkylamino)alkyl-disubstituted pyrimido [5,6,1-de]acridines, a novel group of anticancer agents active on a multidrug resistant cell line. J. Med. Chem. 38:3282; 1995.
50. Horton, D.; Priebe, W.; Varela, O. Synthesis and antitumor activity of 3-deamino-3′-hydroxydoxorubicin. A facile procedure for the preparation of doxorubicin analogs. J. Antibiot. 37:853; 1984.
51. Horton, D.; Priebe, W. U.S. patent 4.537.882; 1985.
52. Smith, G. C. M.; Tew, D.; Wolf, C. R. Dissection of NADPH-cytochrome P450 oxidoreductase into distinct functional domains. Proc. Natl. Acad. Sci. USA 91:8710; 1994.
53. Azzi, A.; Montecucco, C.; Richter, C. The use of acetylated ferricytochrome c for the detection of superoxide radicals produced in biological membranes. Biochem. Biophys. Res. Commun. 65:597; 1975.
54. Pawlowska, J.; Tarasiuk, J.; Borowski, E.; Wasowska, M.; Oszczapowicz, I.; Wolf, C. R. The ability of new formamidine sugar-modified derivatives of daunorubicin to stimulate free radical formation in three enzymatic systems: NADH dehydrogenase, NADPH cytochrome P450 reductase and xanthine oxidase. Acta Biochim. Pol. 47: 141; 2000.
55. Hille, R.; Nishino, T. Flavoprotein structure and mechanism. 4. Xanthine oxidase and xanthine dehydrogenase. FASEB J. 9:995; 1995.