Synthesis and characterization of a practically better DEPMPO-type spin trap, 5-(2,2-dimethyl-1,3-propoxy cyclophosphoryl)-5-methyl-1-pyrroline N-oxide (CYPMPO).
5-(2,2-dimethyl-1,3-propoxy cyclophosphoryl)-5-methyl-1-pyrroline N-oxide (CYPMPO), a new cyclic DEPMPO-type nitrone was evaluated for spin-trapping capabilities toward hydroxyl and superoxide radicals. CYPMPO is colorless crystalline and freely soluble in water. Both the solid and diluted aqueous solution did not develop electron spin resonance (ESR) signal for at least 1 month at ambient conditions. CYPMPO can spin-trap superoxide and hydroxyl radicals in both chemical and biological systems, and the ESR spectra are readily assignable. Half life for the superoxide adduct of CYPMPO produced in UV-illuminated hydrogen peroxide solution was approximately 15 min, and in biological systems such as hypoxanthine (HX)/xanthine oxidase (XOD) the half-life of the superoxide adduct was approximately 50 min. In UV-illuminated hydrogen peroxide solution, there was no conversion from the superoxide adduct to the hydroxyl adduct. Although overall spin-trapping capabilities of CYPMPO are similar to DEPMPO, its high melting point, low hygroscopic property, and the long shelf-life would be highly advantageous for the practical use.
Kamibayashi
Masato
M
Kyoto Pharmaceutical University, Yamashina, Kyoto, 607-8412, Japan.
Oowada
Shigeru
S
Kameda
Hiroaki
H
Okada
Taiichi
T
Inanami
Osamu
O
Ohta
Shunsaku
S
Ozawa
Toshihiko
T
Makino
Keisuke
K
Kotake
Yashige
Y
D003497:Cyclic N-Oxides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D018736:DNA Adducts; D004578:Electron Spin Resonance Spectroscopy / Q000295:instrumentation; D006861:Hydrogen Peroxide / Q000494:pharmacology; D006863:Hydrogen-Ion Concentration; D017665:Hydroxyl Radical; D007700:Kinetics; D008956:Models, Chemical; D011758:Pyrroles / Q000737:chemistry* / Q000494:pharmacology; D013113:Spin Labels; D019097:Spin Trapping / Q000379:methods*; D013481:Superoxides / Q000737:chemistry; D013997:Time Factors; D014466:Ultraviolet Rays
C510912:(diethoxyphosphoryl)-5-methylpyrroline N-oxide; C516729:5-(2,2-dimethyl-1,3-propoxy cyclophosphoryl)-5-methyl-1-pyrroline N-oxide; D003497:Cyclic N-Oxides; D018736:DNA Adducts; D011758:Pyrroles; D013113:Spin Labels; D013481:Superoxides; D017665:Hydroxyl Radical; D006861:Hydrogen Peroxide