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Abstract
In this study we report the synthesis and biological application of a novel cyclic nitrone spin trap containing a phosphonium cation. This new spin trap ([4-(2-methyl-1-oxy-3, 4-dihydro-2H-pyrrole-2-carbonyloxy)-butyl]-triphenyl-phosphonium bromide, MitoBMPOBr) is a derivative of the cyclic nitrone, 5-tert-butoxycarbonyl 5-methyl-1-pyrroline N-oxide (BMPO). MitoBMPOBr forms radical adducts upon trapping of superoxide and hydroxyl radicals that exhibit highly distinct and characteristic EPR spectra. The stability of these adducts is comparable to those of BMPO. Because of the presence of a positively-charged phosphonium moiety, MitoBMPOBr may be suitable for trapping reactive oxygen species (ROS) in the mitochondria.
| Abbreviations | ||
| BMPO | = | 5-tert-butoxycarbonyl 5-methyl-1-pyrroline N-oxide |
| Boc | = | tert-butoxycarbonyl |
| DEPMPO | = | 5-(diethoxyphosphoryl)-5-methyl-1-pyrroline N-oxide |
| DMPO | = | 5,5-dimethyl-1-pyrroline N-oxide |
| EMPO | = | 5-ethoxycarbonyl-5-methyl-pyrroline N-oxide |
| EPR | = | electron paramagnetic resonance |
| LC–MS | = | liquid chromatography and mass spectrometry |
| MitoBMPOBr | = | [4-(2-methyl-1-oxy-3,4-dihydro-2H-pyrrole-2-carbonyloxy)-butyl]-triphenyl-phosphonium bromide |
| MitoPBN | = | [4-[4-[[(l,l-dimethylethyl)oxidoimino]methyl]phenoxy]butyl]triphenylphosphonium bromide |
| m-CPBA | = | m-chloroperbenzoic acid |
| NMR | = | nuclear magnetic resonance |
| PBN | = | α-phenyl-N-tert-butyl nitrone |
| Abbreviations | ||
| BMPO | = | 5-tert-butoxycarbonyl 5-methyl-1-pyrroline N-oxide |
| Boc | = | tert-butoxycarbonyl |
| DEPMPO | = | 5-(diethoxyphosphoryl)-5-methyl-1-pyrroline N-oxide |
| DMPO | = | 5,5-dimethyl-1-pyrroline N-oxide |
| EMPO | = | 5-ethoxycarbonyl-5-methyl-pyrroline N-oxide |
| EPR | = | electron paramagnetic resonance |
| LC–MS | = | liquid chromatography and mass spectrometry |
| MitoBMPOBr | = | [4-(2-methyl-1-oxy-3,4-dihydro-2H-pyrrole-2-carbonyloxy)-butyl]-triphenyl-phosphonium bromide |
| MitoPBN | = | [4-[4-[[(l,l-dimethylethyl)oxidoimino]methyl]phenoxy]butyl]triphenylphosphonium bromide |
| m-CPBA | = | m-chloroperbenzoic acid |
| NMR | = | nuclear magnetic resonance |
| PBN | = | α-phenyl-N-tert-butyl nitrone |