5-(Diethoxyphosphoryl)-5-methyl-1-pyrroline N-oxide: a new efficient phosphorylated nitrone for the in vitro and in vivo spin trapping of oxygen-centered radicals.
5-(Diethoxyphosphoryl)-5-methyl-1-pyrroline N-oxide (DEPMPO, 2), a new spin trap, has been synthesized via a two-step synthetic route, and its ability to spin trap oxy radicals in biological milieu has been addressed. The in vitro spin trapping of hydroxyl and superoxide radicals was investigated in a phosphate buffer 0.1 M, and the hyperfine coupling constants of the spin adducts were determined. The rates of spin trapping of hydroxyl and superoxide radicals with 2 were found to be close to those reported for 5,5-dimethyl-1-pyrroline N-oxide (DMPO). However, the DEPMPO-superoxide spin adduct was shown to be significantly more persistent (15 times at pH 7) than the DMPO--superoxide spin adduct. Using 2 as a spin trap, the production of superoxide has been clearly characterized during the reperfusion of ischemic isolated rat hearts.
Frejaville
C
C
Laboratoire Structure et Réactivité des Espèces Paramagnétiques, Université de Provence, Centre de St Jérôme, Marseille, France.
Karoui
H
H
Tuccio
B
B
Le Moigne
F
F
Culcasi
M
M
Pietri
S
S
Lauricella
R
R
Tordo
P
P
D000818:Animals; D003497:Cyclic N-Oxides; D004578:Electron Spin Resonance Spectroscopy; D006878:Hydroxides / Q000737:chemistry*; D007700:Kinetics; D008297:Male; D009589:Nitrogen Oxides; D051381:Rats; D017208:Rats, Wistar; D017382:Reactive Oxygen Species; D015427:Reperfusion Injury / Q000378:metabolism; D013113:Spin Labels; D013481:Superoxides / Q000737:chemistry*
D003497:Cyclic N-Oxides; D006878:Hydroxides; D009589:Nitrogen Oxides; D017382:Reactive Oxygen Species; D013113:Spin Labels; C015388:nitrones; D013481:Superoxides