Stable reduction product of misonidazole.
Int J Radiat Oncol Biol Phys
; 12(7): 1227-30, 1986 Jul.
Article
em En
| MEDLINE
| ID: mdl-3744942
ABSTRACT
The predominant stable product (greater than 80%) of the anaerobic radiation chemical reduction (pH 7, formate, N2O) of misonidazole (MISO) has been identified as the cyclic guanidinium ion MISO-DDI, a 4,5-dihydro-4,5-dihydroxyimidazolium ion. This cation was prepared as its sulfate salt by the reaction of glyoxal and the appropriate N-substituted guanidinium sulfate. Its formation during MISO reduction was established by NMR spectral comparison and by derivatization as glyoxal bis-oxime, which was formed in 86% yield in fully reduced systems. The toxicity of pure MISO-DDI X sulfate was examined in vivo (C3H mice) and in vitro (CHO cells). This product is less toxic than the parent MISO and free glyoxal. A reactive, short-lived, intermediate is suggested as the agent responsible for the toxicity of MISO under hypoxic conditions.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Misonidazol
Limite:
Animals
Idioma:
En
Ano de publicação:
1986
Tipo de documento:
Article