Inhibition of anthracycline semiquinone formation by ICRF-187 (Dexrazoxane) in cells

Free Radical Biology and Medicine - Tập 20 - Trang 905-914 - 1996
Krisztina L. Malisza1, Brian B. Hasinoff1
1Faculty of Pharmacy, University of Manitoba, Winnipeg, Manitoba R3T 2N2 Canada

Tài liệu tham khảo

Gianni, 1983, The biochemical basis of anthracycline toxicity and anti-tumor activity, Rev. Biochem. Toxicol., 5, 1 Weiss, 1992, The anthracyclines: Will we ever find a better doxorubicin?, Semin. Oncol., 19, 670 Gutteridge, 1984, Lipid peroxidation and possible hydroxyl radical formation stimulated by the self-reduction of a doxorubicin-iron(III) complex, Biochem. Pharmacol., 33, 1725, 10.1016/0006-2952(84)90340-X Gianni, 1985, Characterization of the cycle of iron-mediated electron transfer from adriamycin to molecular oxygen, J. Biol. Chem., 260, 6820, 10.1016/S0021-9258(18)88854-8 Halliwell, 1989 Bachur, 1979, NADPH cytochrome P-450 reductase activation of quinone anticancer agents to free radicals, 76, 954 Sato, 1977, Electron spin resonance study on the mode of generation of free radicals of daunomycin, adriamycin, and carboquone in NAD(P)H-microsome system, Gann, 68, 603 Kalyanaraman, 1980, Spin-trapping and direct electron spin resonance investigations of the redox metabolism of quinone anticancer drugs, Biochim. Biophys. Acta, 630, 119, 10.1016/0304-4165(80)90142-7 Hoey, 1988, A comparison of the free radical properties of several anthracycline anti-tumour drugs and some of their analogues, Free Radic. Res. Commun., 5, 169, 10.3109/10715768809066926 Zweier, 1986, Differences in O2 reduction by the iron complexes of adriamycin and daunomycin: The importance of the sidechain hydroxyl group, Biochim. Biophys. Acta, 884, 326, 10.1016/0304-4165(86)90181-9 Hasinoff, 1990, Oxyradical production results from the Fe3+-doxorubicin complex undergoing self-reduction by its a-ketol group, Biochem. Cell. Biol., 68, 1331, 10.1139/o90-195 Speyer, 1992, ICRF-187 permits longer treatment with doxorubicin in women with breast cancer, J. Clin. Oncol., 10, 117, 10.1200/JCO.1992.10.1.117 Hasinoff, 1989, The interaction of the cardioprotective agent ICRF-187 ((+)-1,2-bis(3,5-dioxopiperazinyl-1-yl)propane), its hydrolysis product ICRF-198, and other chelating agents with the Fe(III) and Cu (II) complexes of adriamycin, Agents Actions, 26, 378, 10.1007/BF01967305 Hasinoff, 1990, The iron(III) and copper(II) complexes of adriamycin promote the hydrolysis of the cardioprotective agent ICRF-187 ((+)-1,2-bis(3,5-dioxopiperazinyl-1-yl)propane), Agents Actions, 29, 374, 10.1007/BF01966470 Huang, 1982, Metal binding by pharmaceuticals. Part 2. Interactions of Ca(II), Cu(II), Fe(II), Mg(II), Mn(II) and Zn(II) with the intracellular hydrolysis products of the antitumor agent ICRF-159 and its inactive homologue ICRF-192, Agents Actions, 12, 536, 10.1007/BF01965940 Buss, 1993, The one-ring open hydrolysis product intermediates of the cardioprotective agent ICRF-187 (dexrazoxane) displace iron from iron-anthracycline complexes, Agents Actions, 40, 86, 10.1007/BF01976756 Dawson, 1975, Studies on the stability and cellular distribution of dioxopiperazines in cultured BHK-21S cells, Biochem. Pharmacol., 24, 2249, 10.1016/0006-2952(75)90262-2 Hasinoff, 1995, NADPH-cytochrome-P450 reductase promotes hydroxyl radical production by the iron complex of ADR-925, the hydrolysis product of ICRF-187 (dexrazoxane), Free Radic. Res., 22, 319, 10.3109/10715769509145644 Malisza, 1995, Doxorubicin reduces the iron (III) complexes of the hydrolysis products of the antioxidant cardioprotective agent dexrazoxane (ICRF-187) and produces hydroxyl radicals, Arch. Biochem. Biophys., 316, 680, 10.1006/abbi.1995.1091 Von Hoff, 1979, Risk factors for doxorubicin-induced congestive heart failure, Ann. Intern. Med., 91, 710, 10.7326/0003-4819-91-5-710 Von Hoff, 1977, Daunomycin-induced cardiotoxicity in children and adults, 62, 200 Burke, 1987, The structural basis for anthracycline antibiotic stimulation of oxygen consumption by HL-60 cells and mitochondria, Cancer Biochem. Biophys., 9, 245 1989 Swartz, 1972, Biological applications of electron spin resonance, 100 Tarasiuk, 1992, Thermodynamics of the anthracycline-nuclei interactions in drug-resistant and drug-sensitive K562 cells, Biochem. Pharmacol., 43, 2575, 10.1016/0006-2952(92)90146-A Kalyanaraman, 1991, An electron paramagnetic resonance study of the interactions between the adriamycin semiquinone, hydrogen peroxide, iron-chelators, and radical scavengers, Arch. Biochem. Biophys., 286, 164, 10.1016/0003-9861(91)90023-C Alegria, 1989, Free radicals induced by adriamycin-sensitive and adriamycinresistant cells: A spin trapping study, Biochemistry, 28, 8653, 10.1021/bi00447a056 Fisher, 1992, NAD(P)H (quinone acceptor) oxidoreductase (DT-diaphorase)-mediated two-electron reduction of anthraquinone-based antitumor agents and generation of hydroxyl radicals, Biochem. Pharmacol., 43, 575, 10.1016/0006-2952(92)90581-3 Hasinoff, 1994, An HPLC and spectrophotometric study of the hydrolysis of ICRF-187 ((+)-1,2-bis(3,5-dioxopiperazinyl-1-yl)propane) and its one-ring opened intermediates, Int. J. Pharmaceut., 107, 67, 10.1016/0378-5173(94)90303-4 Hasinoff, 1994, Pharmacodynamics of the hydrolysis-activation of the cardioprotective agent ICRF-187 ((+)-1,2-bis(3,5-dioxopiperazinyl-l-yl)propane)), J. Pharm. Sci., 83, 64, 10.1002/jps.2600830115 Skovsgaard, 1982, Membrane transport of anthracyclines, Pharmacol. Ther., 18, 293, 10.1016/0163-7258(82)90034-1 Grandi, 1988, Screening of anthracycline analogs, Vol. 6, 571 Berman, 1992, Comparative cellular pharmacology of daunorubicin and idarubicin in human multidrug resistant leukemia cells, Blood, 79, 3267, 10.1182/blood.V79.12.3267.3267 Davies, 1986, Redox cycling of anthracyclines by cardiac mitrochondria. 1. Anthracycline radical formation by NADH dehydrogenase, J. Biol. Chem., 261, 3060, 10.1016/S0021-9258(17)35746-0 Myers, 1988, Biochemical mechanisms of tumor cell kill by the anthracyclines, Vol. 6, 527 Goormaghtigh, 1990, Structure of the adriamycin-cardiolipin complex, 35, 247 Constantinides, 1990, Transverse location of anthracyclines in lipid bilayers, 35, 259 Crane, 1985, Transplasma-membrane redox systems in growth and development, Biochim. Biophys. Acta, 811, 233, 10.1016/0304-4173(85)90013-8 Alegria, 1990, Semiquinones derived from anthraquinone-containing antitumor drugs can partition into phosphatidylcholine bilayers, Biochim. Biophys. Acta, 1035, 51, 10.1016/0304-4165(90)90172-S Friche, 1990, In vitro circumvention of anthracycline-resistance in ehrlich ascites tumor by anthracycline analogues, Biochem. Pharmacol., 39, 1721, 10.1016/0006-2952(90)90117-4 Dorr, 1991, Comparison of cytoxicity in heart cells and tumor cells exposed to to DNA intercalating agents in vitro, Anti-Cancer Drugs, 2, 27, 10.1097/00001813-199102000-00003 Vile, 1989, Microsomal lipid peroxidation induced by Adriamycin, epirubicin, daunorubicin and mitoxantrone: A comparative study, Cancer Chemother. Pharmacol., 24, 105, 10.1007/BF00263129 Yeung, 1989, A functional assessment of the relative cardiotoxicity of adriamycin and epirubicin in the rat, Radiother. Oncol., 15, 275, 10.1016/0167-8140(89)90096-0 Le Bot, 1988, Different cytoxicity and metabolism of doxorubicin, daunorubicin, epirubicin, esorubicin and idarubicin in cultured human and rat hepatocytes, Biochem. Pharmacol., 37, 3877, 10.1016/0006-2952(88)90069-X Tanabe, 1991, Inhibition of topoisomerase II by antitumor agents bis(2,6-dioxopiperazine) derivatives, Cancer Res., 51, 4903 Hasinoff, 1993, The enzymatic ring-opening reactions of the chiral cardioprotective agent (+)(S)-ICRF-187 and its (-)(R)-enantiomer ICRF-186 by dihydropyrimidine amidohydrolase, Drug Metab. Dispos., 21, 883 Hochster, 1992, Pharmacokinetics of the cardioprotector ADR-529 (ICRF-187) in escalating doses combined with fixed-dose doxorubicin, J. Natl. Cancer Inst., 84, 1725, 10.1093/jnci/84.22.1725