Nitrone spin traps and their pyrrolidine analogs in myocardial reperfusion injury: Hemodynamic and ESR implications - Evidence for a cardioprotective phosphonate effect for 5-(diethoxyphosphoryl)-5-methyl1- pyrroline N-oxide in rat hearts

European Journal of Biochemistry

Volumn 254, Issue 2, 1998, Pages 256-265

  Pietri, Sylvia ^a   Liebgott, Thibaut ^a   Fréjaville, Claudine ^a   Tordo, Paul ^a   Culcasi, Marcel ^a  

^a AIX MARSEILLE UNIVERSITY   (France)

Author keywords

Continuous flow ESR; Functional recovery; Ischemia reperfusion injury; Spin trap; Superoxide

Indexed keywords

(2 METHYL 2 PYRROLIDINYL)PHOSPHONIC ACID ETHYL ESTER; 5 (DIETHOXYPHOSPHORYL) 5 METHYL 1 PYRROLIDINE N OXIDE; 5,5 DIMETHYL 1 PYRROLINE 1 OXIDE; PHOSPHONIC ACID DERIVATIVE; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; DRUG EFFECT; HEART MUSCLE INJURY; HEART MUSCLE REPERFUSION; HEART PROTECTION; HEMODYNAMICS; MALE; NONHUMAN; PRIORITY JOURNAL; RAT; REPERFUSION INJURY;

ANIMALS; CYCLIC N-OXIDES; ELECTRON SPIN RESONANCE SPECTROSCOPY; FREE RADICALS; HEMODYNAMIC PROCESSES; KINETICS; MALE; MYOCARDIAL REPERFUSION INJURY; NITROGEN OXIDES; PHOSPHONIC ACIDS; PYRROLIDINES; RATS; RATS, WISTAR; SPIN LABELS;

ANIMALIA;

EID: 0032102275     PISSN: 00142956     EISSN: None     Source Type: Journal    
DOI: 10.1046/j.1432-1327.1998.2540256.x     Document Type: Article

References (50)

1. Simpson, P. J. & Lucchesi, B. R. (1987) Free radicals and myocardial ischemia and reperfusion injury, J. Lab. Clin. Med. 110, 13-30.
2. Bolli, R. (1991) Oxygen-derived free radicals and myocardial reperfusion injury: an overview, Cardiovasc. Drugs Ther. 5, 249-268.
3. Goldhaber, J. I. & Weiss, J. N. (1992) Oxygen free radicals and cardiac reperfusion abnormalities, Hypertension 20, 118-127.
4. Zweier, J. L., Flaherty, J. T. & Weisfeldt, M. L. (1987) Direct measurement of free radical generation following reperfusion of ischemic myocardium, Proc. Natl Acad. Sci. USA 84, 1404-1407.
5. Baker, J. E., Felix, C. C., Olinger, G. N. & Kalyanaraman, B. (1988) Myocardial ischemia and reperfusion: direct evidence for free radical generation by electron spin resonance spectroscopy, Proc. Natl Acad. Sci. USA 85, 2786-2789.
6. Nakazawa, H., Ichimori, K., Shinozaki, Y., Okino, H. & Hori, S. (1988) Is superoxide demonstration by electron-spin resonance spectroscopy really superoxide? Am. J. Physiol. 255, H213-H215.
7. Van der Kraaij, A. M. M., Koster, J. F. & Hagen, W. R. (1989) Reappraisal of the e.p.r.signals in (post)-ischaemic cardiac tissue, Biochem. J. 264, 687-694.
8. Zweier, J. L., Kuppusamy, P., Williams, R., Rayburn, B. K., Smith, D., Weisfeldt, M. L. & Flaherty, J. T. (1989) Measurement and characterization of postischemic free radical generation in the isolated perfused heart, J. Biol. Chem. 264, 18 890-18 895.
9. Ruuge, E. K., Ledenev, A. N., Lakomkin, V. L., Konstantinov, A. A. & Ksenzenko, M. Y. (1991) Free radical metabolites in myocardium during ischemia and reperfusion, Am. J. Physiol. 261 (Suppl.), 81-86.
10. Garlick, P. B., Davies, M. J., Hearse, D. J. & Slater, T. F. (1987) Direct detection of free radicals in the reperfused rat heart using electron spin resonance spectroscopy, Circ. Res. 61, 757-760.
11. Bolli, R., Patel, B. S., Jeroudi, M. O., Lai, E. K. & McCay, P. B. (1988) Demonstration of free radical generation in 'stunned' myocardium of intact dogs with the use of the spin trap α-phenyl N-tert-butyl nitrone, J. Clin. Invest. 82, 476-485.
12. Sekili, S., McCay, P. B., Li, X.-Y, Zughaib, M., Sun, J.-Z., Tang, L., Thornby, J. I. & Bolli, R. (1993) Direct evidence that the hydroxyl radical plays a pathogenetic role in myocardial 'stunning' in the conscious dog and demonstration that stunning can be markedly attenuated without subsequent adverse effects, Circ. Res. 73, 705-723.
13. Nohl, H., Stolze, K., Napetschnig, S. & Ishikawa, T. (1991) Is oxidative stress primarily involved in reperfusion injury of the ischemic heart? Free Radical Biol. & Med. 11, 581-588.
14. Blasig, I. E., Shuter, S., Garlick, P. & Slater, T. (1994) Relative time-profiles for free radical trapping, coronary flow, enzyme leakage, arrhythmias, and function during myocardial reperfusion, Free Radical Biol. & Med. 16, 35-41.
15. Pietri, S., Culcasi, M. & Cozzone, P. J. (1989) Real-time continuous-flow spin trapping of hydroxyl free radical in the ischemic and post-ischemic myocardium, Eur. J. Biochem. 186, 163-173.
16. Arroyo, C. M., Kramer, J. H., Dickens, B. F. & Weglicki, W. B. (1987) Identification of free radicals in myocardial ischemia/reperfusion by spin trapping with nitrone DMPO, FEBS Lett. 221, 101-104.
17. Zweier, J. L. (1988) Measurement of superoxide-derived free radicals in the reperfused heart. Evidence for a free radical mechanism of reperfusion injury, J. Biol. Chem. 263, 1353-1357.
18. Blasig, I. E., Ebert, B., Hennig, C., Pali, T. & Tosaki, A. (1990) Inverse relationship between ESR spin trapping of oxyradicals and degree of functional recovery during myocardial reperfusion in isolated working rat heart, Cardiovasc. Res. 24, 263-270.
19. Tosaki, A. & Braquet, P. (1990) DMPO and reperfusion injury; arrhythmia, heart function, electron spin resonance, and nuclear magnetic resonance studies in isolated working guinea pig hearts, Am. Heart J. 120, 819-830.
20. Tosaki, A., Blasig, I. E., Pali, T. & Ebert, B. (1990) Heart protection and radical trapping by DMPO during reperfusion in isolated working rat hearts, Free Radical Biol. & Med. 8, 363-372.
21. Tosaki, A., Haseloff, R. F., Hellegouarch, A., Schoenheit, K., Martin, V. V., Das, D. K. & Blasig, I. E. (1992) Does the antiarrhythmic effect of DMPO originate from its oxygen radical trapping property or the structure of the molecule itself? Basic Res. Cardiol. 87, 536-547.
22. Nakazawa, H., Arroyo, C. M., Ichimori, K., Saigusa, Y., Minezaki, K. K. & Pronai, L. (1991) The demonstration of DMPO superoxide adduct upon reperfusion using a low non-toxic concentration, Free Radical Res. Commun. 14, 297-302.
23. Fréjaville, C., Karoui, H., Tuccio, B., Le Moigne, F., Culcasi, M., Pietri, S., Lauricella, R. & Tordo, P. (1995) 5-(Diethoxyphosphoryl)-5-methyl-1-pyrroline N-oxide: a new efficient phosphorylated nitrone for the in vitro and in vivo spin trapping of oxygen-centered radicals, J. Med. Chem. 38, 258-265.
24. Hearse, D. J. & Tosaki, A. (1987) Free radicals and reperfusion-induced arrhythmias: protection by the spin trap agent PBN in the rat heart, Circ. Res. 60, 375-383.
25. Charlon, V. & de Leiris, J. (1988) Ability of N-tert-butyl alpha phenylnitrone (PBN) to be used in isolated perfused heart spin trapping experiments: preliminary studies, Basic Res. Cardiol. 83, 306-331.
26. Bradamante, S., Monti, E., Paracchini, L., Lazzarini, E. & Piccinini, F. (1992) Protective activity of the spin trap tert-butyl-α-phenyl nitrone (PBN) in reperfused rat heart, J. Mol. Cell. Cardiol. 24, 375-386.
27. Li, X.-Y., Sun, J.-Z., Bradamante, S., Piccinini, F. & Bolli, R. (1993) Effects of the spin trap α-phenyl N-tert-butyl nitrone on myocardial function and flow: a dose-response study in the open-chest dog and in the isolated rat heart, Free Radical Biol. & Med. 14, 277-285.
28. Hearse, D. J. & Tosaki, A. (1987) Reperfusion-induced arrhythmias and free radicals: studies in the rat heart with DMPO, J. Cardiovasc. Pharmacol. 9, 641-650.
29. Bradamante, S., Jotti, A., Paracchini, L. & Monti, E. (1993) The hydrophilic spin trap, 5,5-dimethyl-1-pyrroline-1-oxide, does not protect the rat heart from reperfusion injury, Eur. J. Pharmacol. 234, 113-116.
30. Konorev, E. A., Baker, J. E., Joseph, J. & Kalyanaraman, B. (1993) Vasodilatory and toxic effects of spin traps on aerobic cardiac function, Free Radical Biol. & Med. 14, 127-137.
31. 31P labeled cyclic nitrones: a new class of spin traps for free radicals in biological milieu, NATO ASI Ser. A Life Sci. 27, 39-47.
32. Rockenbauer, A. & Korecz, L. (1996) Automatic computer simulations of ESR spectra, Appl. Magn. Reson. 10, 29-43.
33. Hanna, P. M., Chamulitrat, W. & Mason, R. P. (1992) When are metal ion-dependent hydroxyl and alkoxyl radical adducts of 5,5-dimethyl-1-pyrroline N-oxide artifacts? Arch. Biochem. Biophys. 296, 640-644.
34. Jennings, R. B., Ganote, C. E. & Reimer, K. A. (1975) Ischemic tissue injury, Am. J. Pathol. 81, 179-198.
35. Merchant, F. J., Feinberg, H. & Levitsky, S. (1974) Sequential analysis of altered myocardial metabolism and contractility induced by normothermic arrest and reperfusion, J. Surg. Res. 16, 153-161.
36. Robinson, L. A., Braimbridge, M. V., Hearse, D. J. & Jones, R. H. (1984) Creatine phosphate: and additive myocardial protective and antiarrhythmic agent in cardioplegia, J. Thorac. Cardiovasc. Surg. 87, 190-200.
37. Sharov, V. G., Saks, V. A., Kupriyanov, V. V., Lakomkin, V. L., Kapelko, V. I., Steinschneider, A. Ya. & Javadov, S. A. (1987) Protection of ischemic myocardium by exogenous phosphocreatine. I. Morphologic and phosphorus 31-nuclear magnetic resonance studies, J. Thorac. Cardiovasc. Surg. 94, 749-761.
38. Zucchi, R., Poddighe, R., Limbruno, U., Mariani, M., Ronca-Testoni, S. & Ronca, G. (1989) Protection of isolated rat heart from oxidative stress by exogenous creatine phosphate, J. Mol. Cell. Cardiol. 21, 67-73.
39. Conorev, E. A., Sharov, V. G. & Saks, V. A. (1991) Improvement in contractile recovery of isolated rat heart after cardioplegic ischaemic arrest with endogenous phosphocreatine: involvement of antiperoxidative effect? Cardiovasc. Res. 25, 164-171.
40. Pissarek, M., Jänichen, F., Blasig, I. E., Haseloff, R., Keller, T, Tapp, E. & Krause, E.-G. (1995) Cardioprotective potency of the radical scavenger S-2-(3-aminopropylamino) ethylphosphorothioic acid in the post-ischaemic rat heart, Mol. Cell. Biochem. 145, 121-129.
41. Cova, D., De Angelis, L., Monti, E. & Piccinini, F. (1992) Subcellular distribution of two spin trapping agents in rat heart: possible explanation for their different protective effets against doxorubicin-induced cardiotoxicity, Free Rad. Res. Commun. 15, 353-360.
42. Anderson, D. E., Yuan, X.-J., Tseng, C.-M., Rubin, L. J., Rosen, G. M. & Tod, M. L. (1993) Nitrone spin traps block calcium channels and induce pulmonary artery relaxation independent of free radicals, Biochem. Biophys. Res. Commun. 193, 878-885.
43. Hankovszky, O. H., Hideg, K., Bödi, I. & Frank, L. (1986) New antiarrhythmic agents.2,2,5,5-tetramethyl-3-pyrroline-3-carboxamides and 2,2,5,5-tetramethylpyrrolidine-3-carboxamides, J. Med. Chem. 29, 1138-1152.
44. Twomey, P., Taira, J., DeGraff, W., Mitchell, J. B., Russo, A., Krishna, M. C., Hankovszky, O. H., Frank, L. & Hideg, K. (1997) Direct evidence for in vivo nitroxide free radical production from a new antiarrhythmic drug by EPR spectroscopy, Free Radical Biol. & Med. 22, 909-916.
45. Samuni, A., Krishna, C. M., Mitchell, J. B., Collins, C. R. & Russo, A. (1990) Superoxide reaction with nitroxides, Free Radical Res. Commun. 9, 241-249.
46. Gelvan, D., Saltman, P. & Powell, S. R. (1991) Cardiac reperfusion damage prevented by a nitroxide free radical, Proc. Natl Acad. Sci. USA 88, 4680-4684.
47. Rosen, G. M., Halpern, H. J., Brunsting, L. A., Spencer, D. P., Strauss, K. E., Bowman, M. K. & Wechsler, A. S. (1988) Direct measurement of nitroxide pharmacokinetics in isolated hearts situated in a low-frequency electron spin resonance spectrometer: Implications for spin trapping and in vivo oxymetry, Proc. Natl Acad. Sci. USA 85, 7772-7776.
48. Pou, S., Nguyen, S. F., Gladwell, T. & Rosen, G. M. (1995) Does peroxynitrite generate hydroxyl radical? Biochim. Biophys. Acta 1244, 62-68.
49. Makino, K., Imaishi, H., Morinishi, S., Hagiwara, T., Takeuchi, T. & Murakami, A. (1989) An artifact in the ESR spectrum obtained by spin trapping with DMPO, Free Radical Res. Commun. 6, 19-28.
50. Pou, S., Hassett, D. J., Britigan, B. E., Cohen, M. S. & Rosen, G. M. (1989) Problems associated with spin trapping oxygen-centered free radicals in biological systems, Anal. Biochem. 177, 1-6.