EPR detection of lipid-derived free radicals from PUFA, LDL, and cell oxidations

Free Radical Biology and Medicine

Volumn 29, Issue 6, 2000, Pages 568-579

  Qian, Steven Yue ^a   Wang, Hong P ^a   Schafer, Freya Q ^a   Buettner, Garry R ^a  

^a UNIVERSITY OF IOWA   (United States)

Author keywords

EPR; Free radicals; Lipid peroxidation; Photosensitizer; Singlet oxygen; Spin trapping

Indexed keywords

5,5 DIMETHYL 1 PYRROLINE 1 OXIDE; FREE RADICAL; LOW DENSITY LIPOPROTEIN; OXYGEN RADICAL; POLYUNSATURATED FATTY ACID;

ARTICLE; DIAGNOSTIC VALUE; ELECTRON SPIN RESONANCE; EXTRACTION; HUMAN; HUMAN CELL; LIPID PEROXIDATION; OXIDATION; PHOTOSENSITIZATION; PRIORITY JOURNAL; SPIN TRAPPING;

ACETATES; CYCLIC N-OXIDES; DIHEMATOPORPHYRIN ETHER; DOCOSAHEXAENOIC ACIDS; ELECTRON SPIN RESONANCE SPECTROSCOPY; FATTY ACIDS, UNSATURATED; FREE RADICALS; HALF-LIFE; HUMAN; K562 CELLS; LIGHT; LINOLEIC ACID; LIPID PEROXIDATION; LIPID PEROXIDES; LIPIDS; LIPOPROTEINS, LDL; MOLECULAR STRUCTURE; SPECTROPHOTOMETRY, ULTRAVIOLET; SUPPORT, U.S. GOV'T, P.H.S.; TUMOR CELLS, CULTURED;

EID: 0034665326     PISSN: 08915849     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0891-5849(00)00407-X     Document Type: Article

References (48)

1. Marnett, L. J.; Wilcox, A. L. The chemistry of lipid alkoxyl radicals and their role in metal-amplified lipid peroxidation. In: Rice-Evans, C.; Halliwell, B.; Lunt, G. G., eds. Free radicals and oxidative stress: environment, drugs and food additives (Biochemical Society Symposium, Vol. 61). London: Portland Press; 1995:65-72.
2. Wilcox A.L., Marnett L.J. Polyunsaturated fatty acid alkoxyl radicals exist as carbon-centered epoxyallylic radicals a key step in hydroperoxide-amplified lipid peroxidation . Chem. Res. Toxicol. 6:1993;413-416.
3. Girotti A.W. Mechanisms of lipid peroxidation. Free Radic. Biol. Med. 1:1985;87-95.
4. Gardner H.W. Oxygen radical chemistry of polyunsaturated fatty acids. Free Radic. Biol. Med. 7:1989;65-86.
5. Wagner B.A., Buettner G.R., Burns C.P. Free radical-mediated lipid peroxidation in cells oxidizability is a function of cell lipid bis-allylic hydrogen content . Biochemistry. 33:1994;4449-4453.
6. Wagner B.A., Buettner G.R., Burns C.P. Increased generation of lipid-derived and ascorbate free radicals by L1210 cells exposed to the ether lipid edelfosine. Cancer Res. 53:1993;711-713.
7. Buettner G.R., Kelley E.E., Burns C.P. Membrane lipid free radicals produced from L1210 murine leukemia cells by Photofrin photosensitization An EPR spin trapping study . Cancer Res. 53:1993;3670-3673.
8. Qian S.Y., Buettner G.R. Iron and dioxygen chemistry is an important route to initiation of biological free radical oxidations an electron paramagnetic resonance spin trapping study . Free Radic. Biol. Med. 26:1999;1447-1456.
9. Kelley E.E., Buettner G.R., Burns C.P. Production of lipid-derived free radicals in L1210 murine leukemia cells is an early event in the photodynamic action of Photofrin. Photochem. Photobiol. 64:1997;576-580.
10. Wagner B.A., Buettner G.R., Oberley L.W., Burns C.P. Sensitivity of K-562 and HL60 cells to edelfosin, an ether lipid drug, correlates with production of active oxygen species. Cancer Res. 58:1998;2809-2816.
11. Schafer F., Buettner G.R. Acidic pH amplifies iron-mediated lipid peroxidation in cells. Free Radic. Biol. Med. 28:2000;1175-1181.
12. Chamulitrat W., Hughes M.F., Eling T.E., Mason R.P. Superoxide and peroxyl radical generation from the reduction of polyunsaturated fatty acid hydroperoxides by soybean lipoxygenase. Arch. Biochem. Biophys. 290:1991;153-159.
13. Davies M.J. Detection of peroxyl and alkoxyl radicals produced by reaction of hydroperoxides with heme-proteins by electron spin resonance spectroscopy. Biochim. Biophys. Acta. 964:1988;28-35.
14. Davies M.J., Slater T.F. Studies on the metal-ion and lipoxygenase-catalysed breakdown of hydroperoxides using electron-spin-resonance spectroscopy. Biochem. J. 245:1987;167-173.
15. Schaich K.M., Borg D.C. Solvent effects in the spin trapping of lipid oxyl radicals. Free Radic. Res. Comm. 9:1990;267-278.
16. Kocherginsky, N.; Swartz, H. M. Chemical reactivity of nitroxides. In: Kocherginsky, N.; Swartz, H. M., eds. Nitroxide spin labels: reactions in biology and chemistry. Boca Raton, FL: CRC Press; 1995:48-49.
17. McCay P.B., Lai E.K., Poyer J.L., DuBose C.M., Janzen E.G. Oxygen- and carbon-centered free radical formation during CCl4 metabolism observation of lipid radicals in vivo and in vitro . J. Biol. Chem. 259:1984;2135-2143.
18. Janzen E.G., Towner R.A., Haire D.L. Detection of free radicals generated from the in-vitro metabolism of carbon tetrachloride using improved ESR spin trapping techniques. Free Radic. Res. Commun. 3:1987;357-364.
19. Albano E., Lott K.A., Slater T.F., Stier A., Symons M.C., Tomasi A. Spin-trapping studies on the free-radical products formed by metabolic activation of carbon tetrachloride in rat liver microsomal fractions isolated hepatocytes and in vivo in the rat. Biochem. J. 204:1982;593-603.
20. Buettner G.R. In the absence of catalytic metals ascorbate does not autoxidize at pH 7 ascorbate as a test for catalytic metals . J. Biochem. Biophys. Methods. 16:1988;27-40.
21. Kotake Y., Reinke L.A., Tanigawa T., Koshida H. Determination of the rate of superoxide generation from biological systems by spin trapping use of rapid oxygen depletion to measure the decay rate of spin adducts . Free Radic. Biol. Med. 17:1994;215-223.
22. Hatch F.T., Lees R.S. Practical methods for plasma lipoprotein analysis. Adv. Lipid Res. 6:1968;2-68.
23. Guffy M.M., North J.A., Burns C.P. Effect of cellular fatty acid alteration on Adriamycin sensitivity in cultured L1210 leukemia cells. Cancer Res. 44:1984;1863-1866.
24. Burns C.P., Wagner B.A. Heightened susceptibility of fish oil polyunsaturate-enriched neoplastic cells to ethane generation during lipid peroxidation. J. Lipid Res. 32:1991;79-87.
25. Burns C.P., Haugstad B.N., Mossman C.J., North J.A., Ingraham L.M. Membrane lipid alteration effect on cellular uptake of mitoxantrone . Lipids. 23:1988;393-397.
26. Li A.S.W., Cummings K.B., Roethling H.P., Buettner G.R., Chignell C.F. A spin trapping database implemented on the IBM PC/AT. J. Magn. Reson. 79:1988;140-142.
27. Buettner G.R. Spin trapping ESR parameters of spin adducts . Free Radic. Biol. Med. 3:1987;259-303.
28. Jori, G. The molecular biology of photodynamic action. In: Pratesi, R.; Succhi, C. A., eds. Lasers in photomedicine and photobiology. Berlin, Germany: Springer-Verlag; 1980:58-66.
29. Thomas J.P., Girotti A.W. Reactivity of photochemically-generated lipid hydroperoxides in cell membranes with glutathione peroxidase. Photochem. Photobiol. 49:1989;153-156.
30. Buettner G.R. On the reaction of superoxide with DMPO/·OOH. Free Radic. Res. Comm. 10:1990;11-15.
31. Krainev, A. G.; Bigelow, D. J. Comparison of 2,2′-azobis (2-amidinopropane) hydrochloride (AAPH) and 2,2′-azobic (2, 4-dimethylvaleronitrile) (AMVN) as free radical initiators: a spin-trapping study. J. Chem. Soc. Perkin Trans. 2. 747-754; 1996.
32. Krainev A.G., Williams T.D., Bigelow D.J. Oxygen-centered spin adducts of 5,5-dimethyl-1-pyrroline N-oxide (DMPO) and 2H-imidazole 1-oxides. J. Magn. Reson. B. 111:1996;272-280.
33. Hanna P.M., Chamulitrat W., Mason R.P. When are metal ion-dependent hydroxyl and alkoxyl radical adducts of 5,5-dimethyl-1-pyrroline. N-oxide artifacts? Arch. Biochem. Biophys. 296:1992;640-644.
34. Chamulitrat W., Iwahashi H., Kelman D.J., Mason R.P. Evidence against the 1:2:2:1 quartet DMPO spectrum as the radical adduct of the lipid alkoxyl radical. Arch. Biochem. Biophys. 296:1992;645-649.
35. Dikalov S.I., Mason R.P. Reassignment of organic peroxyl radical adducts. Free Radic. Biol. Med. 27:1999;864-872.
36. Iwahashi H., Parker C.E., Tomer K.B., Mason R.P. Detection of the ethyl- and pentyl-radical adducts of alpha-(4-pyridyl-1- oxide)-N-tert-butylnitrone in rat-liver microsomes treated with ADP, NADPH and ferric chloride. Free Radic. Res. Commun. 16:1992;295-301.
37. North J.A., Spector A.A., Buettner G.R. Detection of lipid radicals by electron paramagnetic resonance spin trapping using intact cells enriched with polyunsaturated fatty acid. J. Biol. Chem. 267:1992;5743-5746.
38. Iwahashi H., Deterding L.J., Parker C.E., Mason R.P. Tomer, K. B. Identification of radical adducts formed in the reactions of unsaturated fatty acids with soybean lipoxygenase using continuous flow fast atom bombardment with tandem mass spectrometry. Free Radic. Res. 25:1996;255-274.
39. Janzen E.G., Krygsman P.H., Lindsay D.A., Haire D.L. Detection of alkyl, alkoxyl and alkylperoxyl radicals from the thermolysis of azo-bis-(isobutyronitrile) by ESR spin trapping - evidence for the double spin adducts from liquid-phase chromatography and mass spectroscopy. J Am. Chem. Soc. 112:1990;8279-8284.
40. Grossi L., Strazzari S., Gilbert B.C., Whitwood A.C. Oxiranylcarbinyl radicals from allyloxyl radical cyclization characterization and kinetic information via ESR spectroscopy . J. Org. Chem. 63:1998;8366-8372.
41. Buettner G.R., Doherty T.P., Patterson L.K. The kinetics of the reaction of superoxide radical with Fe(III) complexes of EDTA, DETAPAC, and HEDTA. FEBS Lett. 158:1983;143-146.
42. Qian, Y.; Buettner, G. R. The EPR detection of lipid-derived radicals during membrane lipid peroxidation of cells. Free Radic. Biol. Med. 25(Suppl.):S106; 1998.
43. Wang, H.; Buettner, G. R.; Oberley, L. W. Overexpression of human PhGPx in human breast cancer cells (MCF-7): effects on Photofrin photosensitization. Photochem. Photobiol. 69(Suppl.):36S; 1999.
44. Steinberg D., Parthasarathy S., Carew T.E., Khoo J.C., Witztum J.L. Beyond cholesterol modifications of low-density lipoprotein that increase its atherogenicity . N. Engl. J. Med. 320:1989;915-924.
45. Flanagan S.W., Moseley P.L., Buettner G.R. Increased flux of free radicals in cells subjected to hyperthermia detection by electron paramagnetic resonance spin trapping . FEBS Lett. 431:1998;285-286.
46. Ursini F., Maiorino M., Gregolin C. The selenoenzyme phospholipid hydroperoxide glutathione peroxidase. Biochim. Biophys. Acta. 839:1985;62-70.
47. Thomas J.P., Maiorino M., Ursini F., Girotti A.W. Protective action of phospholipid hydroperoxide glutathione peroxidase against membrane-damaging lipid peroxidation. In situ reduction of phospholipid and cholesterol hydroperoxides. J. Biol. Chem. 265:1990;454-461.
48. Schafer F.Q., Buettner G.R. Singlet oxygen toxicity is cell-line dependent a study of lipid peroxidation in nine leukemia cell lines . Photochem. Photobiol. 70:1999;858-867.