18O-Labeled lipid hydroperoxides and HPLC coupled to mass spectrometry as valuable tools for studying the generation of singlet oxygen in biological system |
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Authors: | Miyamoto Sayuri Martinez Glaucia R Martins Ana Paula B Medeiros Marisa H G Di Mascio Paolo |
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Institution: | Departamento de Bioquímica, Instituto de Química, Universidade de S?o Paulo, CP26077, CEP 05513-970, S?o Paulo, SP, Brazil. |
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Abstract: | Decomposition of lipid hydroperoxides (LOOH) is known to generate toxic products capable to induce tissue injury. We have recently confirmed that decomposition of LOOH into peroxyl radicals is a potential source of singlet oxygen ((1)O(2) in biological system. Using (18)O-labeled linoleic acid hydroperoxide (LA(18)O(18)OH) in the presence of Ce(4+) or Fe(2+), we observed the formation of (18)O-labeled (1)O(2) ((18)(1)O(2)]) by chemical trapping of (1)O(2) with 9,10-diphenylanthracene (DPA) and detecting the corresponding (18)O-labeled DPA endoperoxide (DPA(18)O(18)O) by HPLC coupled to tandem mass spectrometry (HPLC-MS/MS). (18)O-Labeled alcohol and ketone were also detected providing further evidence for the generation of (1)O(2) by the Russell mechanism. Similarly the reaction of LA(18)O(18)OH with peroxynitrite also generated (18)(1)O(2)].In conclusion, these results indicates that the use of (18)O-labeled LOOH associated with HPLC-MS/MS can be an useful tool to clarify mechanistic features involved in the reaction of LOOH in biological media. |
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