<sup>•</sup>BMPO-OOH Spin-Adduct as a Model for Study of Decomposition of Organic Hydroperoxides and the Effects of Sulfide/Selenite Derivatives. An EPR Spin-Trapping Approach
Lipid hydroperoxides play an important role in various pathophysiological processes. Therefore, a simple model for organic hydroperoxides could be helpful to monitor the biologic effects of endogenous and exogenous compounds. The electron paramagnetic resonance (EPR) spin-trapping technique is a use...
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MDPI AG
2020-09-01
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| Series: | Antioxidants |
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| Online Access: | https://www.mdpi.com/2076-3921/9/10/918 |
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| author | Anton Misak Vlasta Brezova Marian Grman Lenka Tomasova Miroslav Chovanec Karol Ondrias |
| author_facet | Anton Misak Vlasta Brezova Marian Grman Lenka Tomasova Miroslav Chovanec Karol Ondrias |
| author_sort | Anton Misak |
| collection | DOAJ |
| description | Lipid hydroperoxides play an important role in various pathophysiological processes. Therefore, a simple model for organic hydroperoxides could be helpful to monitor the biologic effects of endogenous and exogenous compounds. The electron paramagnetic resonance (EPR) spin-trapping technique is a useful method to study superoxide (O<sub>2</sub><sup>•−</sup>) and hydroxyl radicals. The aim of our work was to use EPR with the spin trap 5-<i>tert</i>-butoxycarbonyl-5-methyl-1-pyrroline-<i>N</i>-oxide (BMPO), which, by trapping O<sub>2</sub><sup>•−</sup> produces relatively stable <sup>•</sup>BMPO-OOH spin-adduct, a valuable model for organic hydroperoxides. We used this experimental setup to investigate the effects of selected sulfur/selenium compounds on <sup>•</sup>BMPO-OOH and to evaluate the antioxidant potential of these compounds. Second, using the simulation of time-dependent individual BMPO adducts in the experimental EPR spectra, the ratio of <sup>•</sup>BMPO-OH/<sup>•</sup>BMPO-OOH—which is proportional to the transformation/decomposition of <sup>•</sup>BMPO-OOH—was evaluated. The order of potency of the studied compounds to alter <sup>•</sup>BMPO-OOH concentration estimated from the time-dependent <sup>•</sup>BMPO-OH/<sup>•</sup>BMPO-OOH ratio was as follows: Na<sub>2</sub>S<sub>4</sub> > Na<sub>2</sub>S<sub>4</sub>/SeO<sub>3</sub><sup>2−</sup> > H<sub>2</sub>S/SeO<sub>3</sub><sup>2−</sup> > Na<sub>2</sub>S<sub>2</sub> ~Na<sub>2</sub>S<sub>2</sub>/SeO<sub>3</sub><sup>2−</sup> ~H<sub>2</sub>S > SeO<sub>3</sub><sup>2−</sup> ~SeO<sub>4</sub><sup>2−</sup> ~control. In conclusion, the presented approach of the EPR measurement of the time-dependent ratio of <sup>•</sup>BMPO-OH/<sup>•</sup>BMPO-OOH could be useful to study the impact of compounds to influence the transformation of <sup>•</sup>BMPO-OOH. |
| first_indexed | 2024-03-10T16:01:45Z |
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| spelling | doaj.art-6d291db5471446a6857f71070f8c518a2023-11-20T15:12:20ZengMDPI AGAntioxidants2076-39212020-09-0191091810.3390/antiox9100918<sup>•</sup>BMPO-OOH Spin-Adduct as a Model for Study of Decomposition of Organic Hydroperoxides and the Effects of Sulfide/Selenite Derivatives. An EPR Spin-Trapping ApproachAnton Misak0Vlasta Brezova1Marian Grman2Lenka Tomasova3Miroslav Chovanec4Karol Ondrias5Department of Molecular Physiology, Institute of Clinical and Translational Research, Biomedical Research Center, Slovak Academy of Sciences, Dúbravská cesta 9, 84505 Bratislava, SlovakiaFaculty of Chemical and Food Technology, Institute of Physical Chemistry and Chemical Physics, Slovak University of Technology in Bratislava, Radlinského 9, 81237 Bratislava, SlovakiaDepartment of Molecular Physiology, Institute of Clinical and Translational Research, Biomedical Research Center, Slovak Academy of Sciences, Dúbravská cesta 9, 84505 Bratislava, SlovakiaDepartment of Molecular Physiology, Institute of Clinical and Translational Research, Biomedical Research Center, Slovak Academy of Sciences, Dúbravská cesta 9, 84505 Bratislava, SlovakiaDepartment of Genetics, Cancer Research Institute, Biomedical Research Center, Slovak Academy of Sciences, Dúbravská cesta 9, 84505 Bratislava, SlovakiaDepartment of Molecular Physiology, Institute of Clinical and Translational Research, Biomedical Research Center, Slovak Academy of Sciences, Dúbravská cesta 9, 84505 Bratislava, SlovakiaLipid hydroperoxides play an important role in various pathophysiological processes. Therefore, a simple model for organic hydroperoxides could be helpful to monitor the biologic effects of endogenous and exogenous compounds. The electron paramagnetic resonance (EPR) spin-trapping technique is a useful method to study superoxide (O<sub>2</sub><sup>•−</sup>) and hydroxyl radicals. The aim of our work was to use EPR with the spin trap 5-<i>tert</i>-butoxycarbonyl-5-methyl-1-pyrroline-<i>N</i>-oxide (BMPO), which, by trapping O<sub>2</sub><sup>•−</sup> produces relatively stable <sup>•</sup>BMPO-OOH spin-adduct, a valuable model for organic hydroperoxides. We used this experimental setup to investigate the effects of selected sulfur/selenium compounds on <sup>•</sup>BMPO-OOH and to evaluate the antioxidant potential of these compounds. Second, using the simulation of time-dependent individual BMPO adducts in the experimental EPR spectra, the ratio of <sup>•</sup>BMPO-OH/<sup>•</sup>BMPO-OOH—which is proportional to the transformation/decomposition of <sup>•</sup>BMPO-OOH—was evaluated. The order of potency of the studied compounds to alter <sup>•</sup>BMPO-OOH concentration estimated from the time-dependent <sup>•</sup>BMPO-OH/<sup>•</sup>BMPO-OOH ratio was as follows: Na<sub>2</sub>S<sub>4</sub> > Na<sub>2</sub>S<sub>4</sub>/SeO<sub>3</sub><sup>2−</sup> > H<sub>2</sub>S/SeO<sub>3</sub><sup>2−</sup> > Na<sub>2</sub>S<sub>2</sub> ~Na<sub>2</sub>S<sub>2</sub>/SeO<sub>3</sub><sup>2−</sup> ~H<sub>2</sub>S > SeO<sub>3</sub><sup>2−</sup> ~SeO<sub>4</sub><sup>2−</sup> ~control. In conclusion, the presented approach of the EPR measurement of the time-dependent ratio of <sup>•</sup>BMPO-OH/<sup>•</sup>BMPO-OOH could be useful to study the impact of compounds to influence the transformation of <sup>•</sup>BMPO-OOH.https://www.mdpi.com/2076-3921/9/10/918hydroperoxidesantioxidantsEPR spectra simulation<sup>•</sup>BMPO-OOH spin-adductsuperoxideradical |
| spellingShingle | Anton Misak Vlasta Brezova Marian Grman Lenka Tomasova Miroslav Chovanec Karol Ondrias <sup>•</sup>BMPO-OOH Spin-Adduct as a Model for Study of Decomposition of Organic Hydroperoxides and the Effects of Sulfide/Selenite Derivatives. An EPR Spin-Trapping Approach Antioxidants hydroperoxides antioxidants EPR spectra simulation <sup>•</sup>BMPO-OOH spin-adduct superoxide radical |
| title | <sup>•</sup>BMPO-OOH Spin-Adduct as a Model for Study of Decomposition of Organic Hydroperoxides and the Effects of Sulfide/Selenite Derivatives. An EPR Spin-Trapping Approach |
| title_full | <sup>•</sup>BMPO-OOH Spin-Adduct as a Model for Study of Decomposition of Organic Hydroperoxides and the Effects of Sulfide/Selenite Derivatives. An EPR Spin-Trapping Approach |
| title_fullStr | <sup>•</sup>BMPO-OOH Spin-Adduct as a Model for Study of Decomposition of Organic Hydroperoxides and the Effects of Sulfide/Selenite Derivatives. An EPR Spin-Trapping Approach |
| title_full_unstemmed | <sup>•</sup>BMPO-OOH Spin-Adduct as a Model for Study of Decomposition of Organic Hydroperoxides and the Effects of Sulfide/Selenite Derivatives. An EPR Spin-Trapping Approach |
| title_short | <sup>•</sup>BMPO-OOH Spin-Adduct as a Model for Study of Decomposition of Organic Hydroperoxides and the Effects of Sulfide/Selenite Derivatives. An EPR Spin-Trapping Approach |
| title_sort | sup • sup bmpo ooh spin adduct as a model for study of decomposition of organic hydroperoxides and the effects of sulfide selenite derivatives an epr spin trapping approach |
| topic | hydroperoxides antioxidants EPR spectra simulation <sup>•</sup>BMPO-OOH spin-adduct superoxide radical |
| url | https://www.mdpi.com/2076-3921/9/10/918 |
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