Different effectiveness of piperidine nitroxides against oxidative stress induced by doxorubicin and hydrogen peroxide

Cell Biology and Toxicology

Volumn 24, Issue 1, 2008, Pages 101-112

  Czepas, J ^a   Koceva Chyla A ^a   Gwozdzinski K ^a   Jozwiak Z ^a  

^a UNIVERSITY OF LODZ   (Poland)

Author keywords

Cytotoxicity; Doxorubicin; EPR; Hydrogen peroxide; Lipid peroxidation; Nitroxides

Indexed keywords

2,2,6,6 TETRAMETHYLPIPERIDINE 1 OXYL; 4 ACETAMIDO 2,2,6,6 TETRAMETHYLPIPERIDINE 1 OXYL; DOXORUBICIN; HYDROGEN PEROXIDE; NITROXIDE DERIVATIVE; PIPERIDINE DERIVATIVE; TEMPAMINE; TEMPOL; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; BIOLOGICAL ACTIVITY; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG RESPONSE; LIPID PEROXIDATION; NONHUMAN; OXIDATIVE STRESS; PRIORITY JOURNAL;

ANIMALS; CELL DEATH; CELL LINE; CELL MEMBRANE; CELL SURVIVAL; CRICETINAE; CRICETULUS; CYCLIC N-OXIDES; CYTOPROTECTION; DOXORUBICIN; ELECTRON SPIN RESONANCE SPECTROSCOPY; HYDROGEN PEROXIDE; LIPID PEROXIDATION; OXIDATION-REDUCTION; OXIDATIVE STRESS; PIPERIDINES; SPIN LABELS;

EID: 37749011317     PISSN: 07422091     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10565-007-9020-3     Document Type: Article

References (46)

1. Carmichael J, DeGraff WG, Gazdar AF, Minna JD, Mitchell JB. Evaluation of a tetrazolium-based semiautomated colorimetric assay-assessment of chemosensitivity testing. Cancer Res 1987;47:936-42.
2. Constantinides PP, Wang YY, Burke TG, Tritton TR. Transverse location of anthracyclines in lipid bilayers. Paramagnetic quenching studies. Biophys Chem 1990;35:259-64.
3. Demple B. A bridge to control. Science 1998;279:1655-6.
4. Dorr RT. Cytoprotective agents for anthracyclines. Semin Oncol 1996;23:23-34.
5. Gardner AM, Xu FH, Fady C, Jacoby FJ, Duffley DC, Tu Y, et al. Apoptotic vs. nonapoptotic cytotoxicity induced by hydrogen peroxide. Free Radic Biol Med 1997;22:73-83.
6. Gariboldi MB, Rimoldi V, Supino R, Favini E, Monti E. The nitroxide Tempol induces oxidative stress, p21WAF1/CIP1, and cell death in HL60 cells. Free Radic Biol Med 2000;29:633-41.
7. Gariboldi MB, Ravizza R, Petterino C, Castagnaro M, Finocchiaro G, Monti E. Study of in vitro and in vivo effects of the piperidine nitroxide Tempol-a potential new therapeutic agent for gliomas. Eur J Cancer 2003;39:829-37.
8. Gariboldi MB, Terni F, Ravizza R, Meschini S, Marra M, Condello M, et al. The nitroxide Tempol modulates anthracycline resistance in breast cancer cells. Free Radic Biol Med 2006;40:1409-18.
9. Gewirtz DA. A critical evaluation of the mechanisms of action proposed for the antitumor effects of the anthracycline antibiotics adriamycin and daunomycin. Biochem Pharmacol 1999;57:727-41.
10. Głȩbska J, Pułaski L, Gwoździński K, Skolimowski J. Structure-activity relationship studies of protective function of nitroxides in Fenton system. Biometals 2001;14:159-70.
11. Głȩbska J, Skolimowski J, Kudzin Z, Gwoździń ski K, Grzelak A, Bartosz G. Pro-oxidative activity of nitroxides in their reactions with glutathione. Free Radic Biol Med 2003;35:310-6.
12. Halliwell B, Aruoma OI. DNA damage by oxygen-derived species. Its mechanism and measurement in mammalian systems. FEBS Lett 1991;281:9-19.
13. Halliwell B, Gutteridge JM. Formation of thiobarbituric-acid-reactive substance from deoxyribose in the presence of iron salts: the role of superoxide and hydroxyl radicals. FEBS Lett 1981;128:347-52.
14. Jabs J. Reactive oxygen intermediates as mediators of programmed cell death in plants and animals. Biochem Pharmacol 1999;57:231-45.
15. Jȩdrzejczak M, Koceva-Chyła A, Gwoździński K, Jóźwiak Z. Changes in plasma membrane fluidity of immortal rodent cells induced by anticancer drugs doxorubicin, aclarubicin and mitoxantrone. Cell Biol Int 1999;23:497-506.
16. Koceva-Chyła A, Kochman A, Głȩbska J, Gwoździński K, Jóźwiak Z, Metodiewa D. Tempicol-3, a novel piperidine-N-oxide stable radical and antioxidant, with low toxicity acts as apoptosis inducer and cell proliferation modifier of Yoshida sarcoma cells in vivo. Anticancer Res 2000;20:4611-8.
17. Koceva-Chyła A, Sokal A, Kania K, Gwoździński K, Jóźwiak Z. The nitroxides pirolin and pirolid protect the plasma membranes of rat cardiomyocytes against damage induced by anthracyclines. Cell Moll Biol Lett 2003;8:171-7.
18. Kovacic P, Osuna JA Jr. Mechanisms of anti-cancer agents: emphasis on oxidative stress and electron transfer. Curr Pharm Des 2000;6:277-309.
19. 2 or as SOD mimics? J Biol Chem 1996a;271:26026-31.
20. Krishna MC, Samuni A, Taira J, Goldstein S, Mitchell JB, Russo A. Stimulation by nitroxides of catalase-like activity of hemeproteins. Kinetics and mechanism. J Biol Chem 1996b;271:26018-25.
21. Krishna MC, DeGraff W, Hankovszky OH, Sar CP, Kalai T, Jeko J, et al. Studies of structure-activity relationship of nitroxide free radicals and their precursors as modifiers against oxidative damage. J Med Chem 1998;41:3477-92.
22. Kroll C, Langner A, Borchert HH. Nitroxide metabolism in the human keratinocyte cell line HaCaT. Free Radic Biol Med 1999;26:850-7.
23. Landolt-Bornstein. New Series II/13c. Berlin: Springer-Verlag; 1983: 183, 218.
24. Link G, Tirosh R, Pinson A, Hershko C. Role of iron in the potentiation of anthracycline cardiotoxicity: identification of heart cell mitochondria as a major site of iron-anthracycline interaction. J Lab Clin Med 1996;127:272-8.
25. Metodiewa D, Koceva-Chyła A, Kochman A, Skolimowski J, Jóźwiak Z. Antiproliferative and cytotoxic effect of N,N-diethyl-aminoethyl ethers of flavanone oximes: a comparison with anthracycline(s), anthraquinone and nitroxides action. Anticancer Res 1999;19:1255-60.
26. Metodiewa D, Skolimowski J, Kochman A, Koceva-Chyła A. The paradoxical apoptotic effects of novel nitroxide antioxidants on Yoshida sarcoma cells in vivo: a commentary. Anticancer Res 2000;20:2593-600.
27. Mizutani H, Tada-Oikawa S, Hiraku Y, Kojima M, Kawanishi S. Mechanism of apoptosis induced by doxorubicin through the generation of hydrogen peroxide. Life Sci 2005;76:1439-53.
28. Monti E, Cova D, Guido E, Morelli R, Oliva C. Protective effect of the nitroxide tempol against the cardiotoxicity of adriamycin. Free Radic Biol Med 1996;21:463-70.
29. Morris S, Sosnovsky G, Hui B, Huber CO, Rao NU, Swartz HM. Chemical and electrochemical reduction rates of cyclic nitroxides (nitroxyls). J Pharm Sci 1991;80:149-52.
30. Nilsson UA, Olsson LI, Carlin G, Bylund-Fellenius AC. Inhibition of lipid peroxidation by spin labels. Relationships between structure and function. J Biol Chem 1989;264:11131-5.
31. Novak I, Harrison LJ, Kovac B, Pratt LM. Electronic structure of persistent radicals: nitroxides. J Org Chem 2004;69:7628-34.
32. Offer T, Russo A, Samuni A. The pro-oxidative activity of SOD and nitroxide SOD mimics. FASEB J 2000;14:1215-23.
33. Ortega-Gutierrez S, Garcia JJ, Martinez-Ballarin E, Reiter RJ, Millan-Plano S, Robinson M, et al. Melatonin improves deferoxamine antioxidant activity in protecting against lipid peroxidation caused by hydrogen peroxide in rat brain homogenates. Neurosci Lett 2002;323:55-9.
34. Rozantsev EG. Svobodnyje iminoksylnyje radicaly. Moscow: Chimia; 1970.
35. Saito K, Takeshita K, Ueda JI, Ozawa T. Two reaction sites of a spin label, TEMPOL (4-hydroxy-2,2,6,6-tetramethylpiperidine-N-oxyl), with hydroxyl radical. J Pharm Sci 2003;92:275-80.
36. Samuni AM, Barenholz Y. Site-activity relationship of nitroxide radical's antioxidative effect. Free Radic Biol Med 2003;34:177-85.
37. Samuni AM, DeGraff W, Krishna MC, Mitchell JB. Nitroxides as antioxidants: Tempol protects against EO9 cytotoxicity. Mol Cell Biochem 2002a;234/235:327-33.
38. Samuni A, Goldstein S, Russo A, Mitchell JB, Krishna MC, Neta P. Kinetics and mechanism of hydroxyl radical and OH-adduct radical reactions with nitroxides and with their hydroxylamines. J Am Chem Soc 2002b;124:8719-24.
39. Scott MD, Meshnick SR, Eaton JW. Superoxide dismutase amplifies organismal sensitivity to ionizing radiation. J Biol Chem 1989;264:2498-501.
40. Shan K, Lincoff AM, Young JB. Anthracycline-induced cardiotoxicity. Ann Intern Med 1996;1:47-58.
41. Skladanowski A, Konopa J. Adriamycin and daunomycin induce programmed cell death (apoptosis) in tumor cells. Biochem Pharmacol 1993;46:375-82.
42. Sun Y, Oberley LW. Redox regulation of transcriptional activators. Free Radic Biol Med 1996;21:335-48.
43. Young RC, Ozols RF, Myers CE. The anthracycline antineoplastic drugs. N Engl J Med 1981;305:139-53.
44. Zhang R, Pinson A, Samuni A. Both hydroxylamine and nitroxide protect cardiomyocytes from oxidative stress. Free Radic Biol Med 1998;24:66-75.
45. Zhang R, Goldstein S, Samuni A. Kinetics of superoxide-induced exchange among nitroxide antioxidants and their oxidized and reduced forms. Free Radic Biol Med 1999;26:1245-52.
46. Zhao QL, Fujiwara Y, Kondo T. Mechanism of cell death induction by nitroxide and hyperthermia. Free Radic Biol Med 2006;40:1131-43.