Redox behaviour of nifuroxazide: generation of the one-electron reduction product.
The electrochemical properties of nifuroxazide have been investigated in aqueous and aqueous-DMF mixed solvents. In aqueous media, a single, irreversible four-electron reduction occurs to give the hydroxylamine derivative. In mixed media, a reversible one-electron reduction to form a nitro radical anion takes place. Cyclic voltammetric studies show that the anion radical product is stable, although the nitro radical anion intermediate shows a tendency to undergo further chemical reactions. A comparison with the voltammetric behaviour of other nitrofurans such as nifurtimox, nitrofurazone and furazolidone is made. The electrochemically-obtained parameters are correlated with the in vivo studies of oxygen consumption on Trypanosoma cruzi cell suspensions.
Squella
J A
JA
Bioelectrochemistry Laboratory, Chemical and Pharmaceutical Sciences Faculty, University of Chile, Santiago, Chile.
Letelier
M E
ME
Lindermeyer
L
L
Nuñez-Vergara
L J
LJ
D000818:Animals; D000890:Anti-Infective Agents / Q000494:pharmacology; D004126:Dimethylformamide / Q000494:pharmacology; D004579:Electron Transport; D005609:Free Radicals / Q000378:metabolism; D006863:Hydrogen-Ion Concentration; D062385:Hydroxybenzoates / Q000494:pharmacology*; D006898:Hydroxylamines / Q000378:metabolism; D007700:Kinetics; D008956:Models, Chemical; D015394:Molecular Structure; D009581:Nitrofurans / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D010084:Oxidation-Reduction; D010100:Oxygen / Q000378:metabolism; D011048:Polarography / Q000379:methods; D013816:Thermodynamics; D014349:Trypanosoma cruzi / Q000378:metabolism
D000890:Anti-Infective Agents; D005609:Free Radicals; D062385:Hydroxybenzoates; D006898:Hydroxylamines; D009581:Nitrofurans; D004126:Dimethylformamide; C013150:nifuroxazide; D010100:Oxygen