Comparison of 2,5,5-trimethyl-1-pyrroline-N-oxide (M3PO) and 3,3,5,5-tetramethyl-1-pyrroline-N-oxide (M4PO) with 5,5-dimethyl-1-pyrroline-N-oxide (DMPO) as spin traps.
2,5,5-Trimethyl-1-pyrroline-N-oxide (M3PO) and 3,3,5,5-tetramethyl-1-pyrroline-N-oxide (M4PO) were examined for their potential as spin traps used in biological samples, and the results obtained for M3PO and M4PO were compared with those of 5,5-dimethyl-1-pyrroline-N-oxide (DMPO) reported previously. The rate constants for the reactions of M3PO and M4PO with hydroxyl radicals were in the same order of that constant of DMPO. The hyperfine splitting constants of M4PO spin adducts were as informative as those of DMPO adducts. In the presence of ferric ions, M3PO and M4PO formed 2-hydroxy-2,5,5-dimethyl-1-pyrrolidinyloxy (M3PO-OH) and 2-hydroxy-3,3,5,5-tetramethyl-1-pyrrolidinyloxyl (M4PO-OH), respectively, by the nucleophilic addition of a water molecule, as we have already reported for DMPO. M4PO-OH was subjected to oxidation by ferric ions with a rate much slower than that for DMPO-OH, while M3PO-OH was not. The results indicate that M4PO is a spin trap suitable for biological applications and that nitrones having a methyl group at C2 represent improved spin traps.
Nishi
M
M
Faculty of Pharmaceutical Sciences, Setsunan University, Osaka, Japan.
Hagi
A
A
Ide
H
H
Murakami
A
A
Makino
K
K
D003497:Cyclic N-Oxides / Q000737:chemistry*; D005290:Ferric Compounds / Q000737:chemistry; D010084:Oxidation-Reduction; D013056:Spectrophotometry, Ultraviolet; D013113:Spin Labels
D003497:Cyclic N-Oxides; D005290:Ferric Compounds; D013113:Spin Labels; C051831:3,3,5,5-tetramethyl-1-pyrroline N-oxide; C077025:2,5,5-trimethyl-1-pyrroline N-oxide; C017245:5,5-dimethyl-1-pyrroline-1-oxide