Spin traps: In vitro toxicity and stability of radical adducts

Free Radical Biology and Medicine

Volumn 34, Issue 11, 2003, Pages 1473-1481

  Khan, Nadeem ^a   Wilmot, Carmen M ^a   Rosen, Gerald M ^b   Demidenko, Eugene ^a   Sun, Jie ^c   Joseph, Joy ^d   O'Hara, Julia ^a   Kalyanaraman, B ^d   Swartz, Harold M ^a  

^a DARTMOUTH MEDICAL SCHOOL   (United States)

^b UNIVERSITY OF MARYLAND SCHOOL OF PHARMACY   (United States)

^c OXIS International Inc   (United States)

^d FREE RADICAL RESEARCH CENTER   (United States)

Author keywords

Cell viability; EPR; ESR spectroscopy; Free radicals; Oxygen consumption rates; Spin trapping; Spin traps; Toxicity

Indexed keywords

5 CARBOXYL 5 METHYL 1 PYRROLINE N OXIDE; 5 DIETHOXYPHOSPHORYL 5 METHYL 1 PYRROLINE 1 OXIDE; 5 ETHOXYCARBONYL 5 METHYL 1 PYRROLINE N OXIDE; 5 TERT BUTOXYCARBONYL 5 METHYL 1 PYRROLINE N OXIDE; 5,5 DIMETHYL 1 PYRROLINE 1 OXIDE; FREE RADICAL; UNCLASSIFIED DRUG;

ANIMAL CELL; AQUEOUS SOLUTION; ARTICLE; CELL FUNCTION; CELL SUSPENSION; CELL VIABILITY; COLONY FORMATION; CONTROLLED STUDY; CYTOTOXICITY; NONHUMAN; OXYGEN CONSUMPTION; PARAMETER; PRIORITY JOURNAL; SPIN TRAPPING; TUMOR CELL LINE;

EID: 0038030710     PISSN: 08915849     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0891-5849(03)00182-5     Document Type: Article

References (34)

1. Janzen E.G. Spin trapping. Methods Enzymol. 105:1984;188-198.
2. Britigan B.E., Cohen M.S., Rosen G.M. Detection of the production of oxygen-centered free radicals by human neutrophils using spin trapping techniques a critical perspective . J. Leukoc. Biol. 41:1987;349-362.
3. Buettner G.R., Mason R.P. Spin-trapping methods for detecting superoxide and hydroxyl free radicals in vitro and in vivo. Methods Enzymol. 186:1990;127-133.
4. Berliner L.J., Khramtsov V., Fujii H., Clanton T.L. Unique in vivo applications of spin traps. Free Radic. Biol. Med. 30:2001;489-499.
5. Kadiiska M.B., Mason R.P. In vivo copper-mediated free radical production an ESR spin-trapping study . Spectrochim. Acta A Mol. Biomol. Spectrosc. 58:2002;1227-1239.
6. Hix S., Kadiiska M.B., Mason R.P., Augusto O. In vivo metabolism of tert-butyl hydroperoxide to methyl radicals. EPR spin trapping and DNA methylation studies. Chem. Res. Toxicol. 13:2000;1056-1064.
7. Kadiiska M.B., Burkitt M.J., Xiang Q.H., Mason R.P. Iron supplementation generates hydroxyl radical in vivo. An ESR spin-trapping investigation. J. Clin. Invest. 96:1995;1653-1657.
8. Dikalova A.E., Kadiiska M.B., Mason R.P. An in vivo ESR spin-trapping study free radical generation in rats from formate intoxication-role of the Fenton reaction . Proc. Natl. Acad. Sci. USA. 98:2001;13549-13553.
9. Kadiiska M.B., Mason R.P. Ethylene glycol generates free radical metabolites in rats an ESR in vivo spin trapping investigation . Chem. Res. Toxicol. 13:2000;1187-1191.
10. Nakao L.S., Kadiiska M.B., Mason R.P., Grijalba M.T., Augusto O. Metabolism of acetaldehyde to methyl and acetyl radicals in vitro and in vivo electron paramagnetic resonance spin-trapping studies . Free Radic. Biol. Med. 29:2000;721-729.
11. Kadiiska M.B., Mason R.P. Acute methanol intoxication generates free radicals in rats an ESR spin trapping investigation . Free Radic. Biol. Med. 28:2000;1106-1114.
12. Halpern H.J., Yu C., Barth E., Peric M., Rosen G.M. In situ detection, by spin trapping of hydroxyl radical markers produced from ionizing radiation in the tumor of a living mouse. Proc. Natl. Acad. Sci. USA. 92:1995;796-800.
13. 2. Free Radic. Biol. Med. 6:1989;179-183.
14. Tordo, P. Spin trapping: recent developments and applications. Electron Spin Resonance 16; 1998.
15. Fréjaville, C., Karoui, H., Tuccio, B., Le Moigne, F.; Culcasi, M.; Pietri, S.; Lauricella, R.; Tordo, P. 5-Diethoxyphosphoryl-5-methyl-1-pyrroline N-oxide (DEPMPO): a new phosphorylated nitrone for efficient in vitro and in vivo spin trapping of oxygen-centred radicals. J. Chem. Soc. Chem. Commun. 1793-1794; 1994.
16. Fréjaville C., Karoui H., Tuccio B., Le Moigne F., Culcasi M., Pietri S., Lauricella R., Tordo. P. 5-Diethoxyphosphoryl-5-methyl-1-pyrroline N-oxide (DEPMPO) a new efficient phosphorylated nitrone for the in vitro and in vivo spin trapping of oxygen-centered radicals . J. Med. Chem. 38:1995;258-265.
17. Finkelstein E., Rosen G.M., Rauckman E.J. Spin trapping. Kinetics of the reaction of superoxide and hydroxyl radicals with nitrones. J. Am. Chem. Soc. 102:1980;4994-4999.
18. Roubaud V., Sankarapandi S., Kuppusamy P., Tordo P., Zweier J.L. Quantitative measurement of superoxide generation using the spin trap 5-(diethoxyphosphoryl)-5-methyl-1-pyrroline-N-oxide. Anal. Biochem. 247:1997;404-411.
19. 1-pyrroline 1-oxides. J. Chem. Soc. 2094-2102; 1959.
20. Zhang H., Joseph J., Vasquez-Vivar J., Karoui H., Nsanzumuhire C., Martasek P., Tordo P., Kalyanaraman B. Detection of superoxide anion using an isotopically labeled nitrone spin trap potential biological applications . FEBS Lett. 473:2000;58-62.
21. Zhao H., Joseph J., Zhang H., Karoui H., Kalyanaraman B. Synthesis and biochemical applications of a solid cyclic nitrone spin trap a relatively superior trap for detecting superoxide anions and glutathiyl radicals . Free Radic. Biol. Med. 31:2001;599-606.
22. Rosen G.M., Tsai P., Weaver J., Porasupharana S., Roman L.J., Starkov A.A., Fiskum G., Pou S. The role of tetrahydrobiopterin in the regulation of neuronal nitric-oxide synthase-generated superoxide. J. Biol. Chem. 277:2002;40275-40280.
23. Fuchs J., Groth N., Herrling T. In vitro and in vivo assessment of the irritation potential of different spin traps in human skin. Toxicology. 151:2000;55-63.
24. Konorev E.A., Baker J.E., Joseph J., Kalyanaraman B. Vasodilatory and toxic effects of spin traps on aerobic cardiac function. Free Radic. Biol. Med. 14:1993;127-137.
25. Haseloff R.F., Mertsch K., Rohde E., Baeger I., Grigor'ev I.A., Blasig I.E. Cytotoxicity of spin trapping compounds. FEBS Lett. 418:1997;73-75.
26. Janzen E.G., Poyer J.L., Schaefer C.F., Downs P.E., DuBose C.M. Biological spin trapping II. Toxicity of nitrone spin traps dose-ranging in the rat . J. Biochem. Biophys. Methods. 30:1995;239-247.
27. Tsai, P.; Elas, M.; Parasca, A. D.; Barth, E. D.; Mailer, C.; Halpern, H. J.; Rosen, G. M. 5-Carboxy-5-methyl-1-pyrroline N-oxide: a spin trap for the hydroxyl radical. J. Chem. Soc. [Perkin 2] 875-880; 2001.
28. Freshney R.I. Culture of animal cells. 3rd ed. 1994;Wiley-Liss, New York.
29. Liu K.J., Miyake M., Panz T., Swartz H. Evaluation of DEPMPO as a spin trapping agent in biological systems. Free Radic. Biol. Med. 26:1999;714-721.
30. Inanami O., Yamamori T., Takahashi T.A., Nagahata H., Kuwabara M. ESR detection of intraphagosomal superoxide in polymorphonuclear leukocytes using 5-(diethoxyphosphoryl)-5-methyl-l-pyrroline-N-oxide. Free Radic. Res. 34:2001;81-92.
31. Stolze K., Udilova N., Nohl H. Spin trapping of lipid radicals with DEPMPO-derived spin traps detection of superoxide, alkyl and alkoxyl radicals in aqueous and lipid phase . Free Radic. Biol. Med. 29:2000;1005-1014.
32. Sentjurc M., Swartz H.M., Kocherginsky N. Metabolism, toxicity, and distribution of spin traps. Sentjurc M., Swartz H.M., Kocherginsky N. Nitroxide spin labels: reactions in biology and chemistry. 1995;199-206 CRC Press, Boca Raton, FL.
33. Swartz H.M., Sentjurc M., Kocherginsky N. Metabolism of nitroxides and their products in cells. Sentjurc M., Swartz H.M., Kocherginsky N. Nitroxide spin labels: reactions in biology and chemistry. 1995;113-147 CRC Press, Boca Raton, FL.
34. Karoui H., Rockenbauer A., Pietri S., Tordo P. Spin trapping of superoxide in the presence of beta-cyclodextrins. Chem. Commun. (Camb.). 24:2002;3030-3031.