Synthesis and ESR studies of a novel cyclic nitrone spin trap attached to a phosphonium group-a suitable trap for mitochondria-generated ROS?
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.
Xu
Yingkai
Y
Department of Biophysics, the Medical College of Wisconsin, Free Radical Research Center, Milwaukee, WI 53226, USA.
Kalyanaraman
B
B
D008928:Mitochondria / Q000378:metabolism*; D009589:Nitrogen Oxides / Q000138:chemical synthesis* / Q000737:chemistry; D009943:Organophosphorus Compounds / Q000138:chemical synthesis*; D011758:Pyrroles / Q000138:chemical synthesis*; D017382:Reactive Oxygen Species / Q000032:analysis*; D013113:Spin Labels / Q000138:chemical synthesis*; D019097:Spin Trapping
C517018:(4-(2-methyl-1-oxy-3, 4-dihydro-2H-pyrrole-2-carbonyloxy)-butyl)-triphenyl-phosphonium bromide; D009589:Nitrogen Oxides; D009943:Organophosphorus Compounds; D011758:Pyrroles; D017382:Reactive Oxygen Species; D013113:Spin Labels; C015388:nitrones