Direct evidence for in vivo nitroxide free radical production from a new antiarrhythmic drug by epr spectroscopy

Free Radical Biology and Medicine

Volumn 22, Issue 5, 1997, Pages 909-916

  Twomey, Patrick ^a   Taira, Junsei ^a   DeGraff, William ^a   Mitchell, James B ^a   Russo, Angelo ^a   Krishna, Murali C ^a   Hankovszky, Olga H ^b   Frank, László ^c   Hideg, Kálmán ^b  

^a NATIONAL CANCER INSTITUTE   (United States)

^b UNIVERSITY OF PÉCS   (Hungary)

^c Alkaloida Chemical Company Ltd   (Hungary)

Author keywords

Cardiac arrhythmias; EPR spectroscopy; Free radicals

Indexed keywords

3 CARBAMOYL 2,2,5,5 TETRAMETHYL 3 PYRROLINE 1 OXYL; ANTIARRHYTHMIC AGENT; FREE RADICAL; NITROXIDE;

ANIMAL CELL; ANTIOXIDANT ACTIVITY; ARTICLE; CHO CELL; DRUG TRANSFORMATION; ELECTRON SPIN RESONANCE; HEART ARRHYTHMIA; HEART MUSCLE ISCHEMIA; NONHUMAN; PRIORITY JOURNAL;

ANIMALS; ANTI-ARRHYTHMIA AGENTS; ANTIOXIDANTS; ARRHYTHMIA; CELL LINE; CRICETINAE; ELECTRON SPIN RESONANCE SPECTROSCOPY; FEMALE; FREE RADICALS; HEMEPROTEINS; HUMANS; MICE; MICE, INBRED C3H; MYOCARDIAL REPERFUSION INJURY; NITROGEN OXIDES; OXIDATION-REDUCTION;

EID: 0031029545     PISSN: 08915849     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0891-5849(96)00477-7     Document Type: Article

References (31)

1. Zweier J. L., Kuppusamy P. Electron paramagnetic resonance measurements of free radicals in the intact beating heart: A technique for detection and characterization of free radicals in whole biological tissues. Proc. Natl. Acad. Sci. USA. 85:1988;5703-5707.
2. McCord J. M. Oxygen-derived radicals: A link between reperfusion injury and inflammation. Fed. Proc. 46:1987;2402-2406.
3. Omar B. A., Flores S. C., McCord J. M. Superoxide dismutase: Pharmacological developments and applications. Adv. Pharmacol. 21:1992;109-161.
4. Mitchell J. B., Samuni A., Krishna M. C., DeGraff W. G., Ahn M. S., Samuni U., Russo A. Biologically active metal-independent superoxide dismutase mimics. Biochemistry. 29:1990;2802-2807.
5. Singh B. N., Vaughan Williams E. M. A fourth class of anti-dysrhythmic action? Effect of verapamil on ouabain toxicity, on atrial and ventricular intracellular potentials, and on other features of cardiac function. Cardiovas. Res. 6:1972;109-119.
6. Hankovszky O. H., Hideg K., Bodi I., Frank L. New antiarrhythmic agents. 2,2,5,5-tetramethyl-3-pyrroline-3-carboxamides and 2,2,5,5-tetramethylpyrrolidines-3-carboxamides. J. Med. Chem. 29:1986;1138-1152.
7. Rozantsev E. G. Free nitroxyl radicals. 1970;Plenum Press, New York.
8. Valvis I. I., Lischick D., Shen D., Sofer S. S. In vitro synthesis of nitroxide free radicals by hog liver microsomes. Free Radic. Biol. Med. 9:1990;345-353.
9. Rosenthal I., Krishna M. C., Yang G. C., Kondo T., Riesz P. A new approach for EPR detection of hydroxyl radicals by reaction with sterically hindered cyclic amines and oxygen. FEBS Lett. 222:1987;75-79.
10. Chen K., Swartz H. M. Oxidation of hydroxylamines to nitroxide spin labels in living cells. Biochem. Biophys. Acta. 970:1988;270-277.
11. Chen K., Glockner J. F., Morse P. D., Swartz H. M. Effects of oxygen on the metabolism of nitroxide spin labels in cells. Biochemistry. 28:1989;2496-2501.
12. Krishna M. C., Grahame D. A., Samuni A., Mitchell J. B., Russo A. Oxoammonium cation intermediate in the nitroxide-catalyzed dismutation of superoxide. Proc. Natl. Acad. Sci. USA. 89:1992;5537-5541.
13. Nilsson U. A., Olsson L. I., Carlin G., Bylund-Fellenius A. C. Inhibition of lipid peroxidation by spin labels. Relationships between structure and function. J. Biol. Chem. 264:1989;11131-11135.
14. 2 decomposition by peroxidases and pseudoperoxidases. Free Radic. Res. Comm. 17:1992;157-175.
15. Gerlock J. L., Zacmanidis P. J., Bauer D. R., Simpson D. J., Blough N. V., Salmeen I. T. Fluorescence detection of free radicals by nitroxide scavenging. Free Radic. Res. Commun. 10:1990;119-121.
16. Samuni A., Godinger D., Aronovitch J., Russo A., Mitchell J. B. Nitroxides block DNA scission and protect cells from oxidative damage. Biochemistry. 30:1991;555-561.
17. Hahn S. M., Krishna C. M., Samuni A., DeGraff W., Cuscela D. O., Johnstone P., Mitchell J. B. Potential use of nitroxides in radiation oncology. Cancer Res. 54:1994;2006s-2010s.
18. Samuni A., Mitchell J. B., DeGraff W., Krishna C. M., Samuni U., Russo A. Nitroxide SOD-mimics: Modes of action. Free Radic. Res. Commun. 12-13:1991;187-194.
19. Mitchell J. B., DeGraff W., Kaufman D., Krishna M. C., Samuni A., Finkelstein E., Ahn M. S., Hahn S. M., Gamson J., Russo A. Inhibition of oxygen-dependent radiation-induced damage by the nitroxide superoxide dismutase mimic, Tempol. Arch. Biochem. Biophys. 289:1991;62-70.
20. Slater A. F. G., Nobel C. S. I., Maellaro E., Bustamante J., Kimland M., Orrenius S. Nitrone spin traps and a nitroxide antioxidant inhibit a common pathway of thymocyte apoptosis. Biochem. J. 306:1995;771-778.
21. Gelvan D., Saultman P., Powell S. Cardiac reperfusion damage prevented by a stable nitroxide free radical. Proc. Natl. Acad. Sci. USA. 88:1991;4680-4684.
22. Hahn S. M., Tochner Z., Krishna C. M., Glass J., Wilson L., Samuni A., Sprague M., Venzon D., Glatstein E., Mitchell J. B., Russo A. Tempol, a stable free radical, is a novel murine radiation protector. Cancer Res. 52:1992;1750-1753.
23. Rachmilewitz D., Karmeli F., Okon E., Samuni A. A novel antiulcergenic stable radical prevents gastric mucosal lesions in rats. Gut. 35:1994;1181-1188.
24. Karmeli F., Eliakim R., Okon E., Samuni A., Rachmilewitz D. A stable nitroxide radical effectively decreases mucosal damage in experimental colitis. Gut. 37:1995;386-393.
25. Niki E. Free radical initiators as a source of water- or lipid-soluble peroxyl radicals. Methods Enzymol. 186B:1990;100-108.
26. Liebmann J., Bourg J., Krishna C. M., Glass J., Cook J. A., Mitchell J. B. Pharmacokinetic properties of nitroxide-labeled albumin in mice. Life Sci. 54:1994;PL503-PL509.
27. Dalaris D., Eddy L., Arduini A., Cadenas E., Hochstein P. Mechanisms of reoxygenation injury in myocardial infarction: Implications of a myoglobin redox cycle. Biochem. Biophys. Res. Commun. 160:1989;1162-1168.
28. Laranjinha J., Almeida L., Madeira V. Reduction of ferrylmyoglobin by dietary phenolic acid derivatives of cinnamic acid. Free Radic. Biol. Med. 19:1995;329-337.
29. Damiani L. A., Case D. E. Metabolism of Heterocyctes. Katritzky A. R., Rees C. W. Comprehensive organic chemistry. 1:1984;223-246 Oxford Press, London.
30. Swartz H. M. Principles of the metabolism of nitroxides and their implications for spin trapping. Free Radic. Res. Commun. 9:1990;399-405.
31. Komarov A. M., Joseph J., Lai C. S. In vivo pharmacokinetics of nitroxides in mice. Biochem. Biophys. Res. Commun. 201:1994;1035-1042.