Reduction of nitroimidazole derivatives by hydrogenosomal extracts of Trichomonas vaginalis. 1985

N Yarlett, and T E Gorrell, and R Marczak, and M Müller

The reduction rate of nitroimidazole derivatives by pyruvate:ferredoxin oxidoreductase activity in ferredoxin depleted hydrogenosomal extracts of Trichomonas vaginalis depended on the one-electron midpoint potential (E7(1)) of 15 compounds out of the 16 tested. The results showed a linear correlation with a positive slope between the logarithm of the rate and the E7(1) in the range from -564 to -260 mV. Addition of T. vaginalis ferredoxin stimulated the reduction. The additional rate (stimulated rate minus basal rate) was proportional to the concentration of ferredoxin and independent of the E7(1) of the compounds. The compound with the most positive E7(1) (-243 mV) was, however, reduced more slowly than expected. These findings indicate that reduction in the presence of ferredoxin is the sum of two processes, i.e. electron transfer directly from pyruvate:ferredoxin oxidoreductase and from reduced ferredoxin generated by pyruvate:ferredoxin oxidoreductase activity. The relative role of ferredoxin in reductive activation of nitroimidazole derivatives is greater for compounds with more negative E7(1) values. This observation correlates with the high selectivity of the more negative 5-nitroimidazoles against anaerobic prokaryotic and eukaryotic microorganisms in which ferredoxin plays an important metabolic role.

UI MeSH Term Description Entries
D007658 Ketone Oxidoreductases Oxidoreductases that are specific for KETONES. Oxidoreductases, Ketone
D009593 Nitroimidazoles IMIDAZOLES having a nitro moiety. Nitroimidazole
D010084 Oxidation-Reduction A chemical reaction in which an electron is transferred from one molecule to another. The electron-donating molecule is the reducing agent or reductant; the electron-accepting molecule is the oxidizing agent or oxidant. Reducing and oxidizing agents function as conjugate reductant-oxidant pairs or redox pairs (Lehninger, Principles of Biochemistry, 1982, p471). Redox,Oxidation Reduction
D005288 Ferredoxins Iron-containing proteins that transfer electrons, usually at a low potential, to flavoproteins; the iron is not present as in heme. (McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Ferredoxin,Ferredoxin I,Ferredoxin II,Ferredoxin III
D000818 Animals Unicellular or multicellular, heterotrophic organisms, that have sensation and the power of voluntary movement. Under the older five kingdom paradigm, Animalia was one of the kingdoms. Under the modern three domain model, Animalia represents one of the many groups in the domain EUKARYOTA. Animal,Metazoa,Animalia
D014246 Trichomonas vaginalis A species of TRICHOMONAS that produces a refractory vaginal discharge in females, as well as bladder and urethral infections in males. Trichomonas vaginali,vaginali, Trichomonas
D050743 Pyruvate Synthase A ferredoxin-containing enzyme that catalyzes the COENZYME A-dependent oxidative decarboxylation of PYRUVATE to acetyl-COENZYME A and CARBON DIOXIDE. Pyruvate Ferredoxin Oxidoreductase,Pyruvate Oxidoreductase,Pyruvate Synthetase,Pyruvate-Ferredoxin Oxidoreductase,Ferredoxin Oxidoreductase, Pyruvate,Oxidoreductase, Pyruvate,Oxidoreductase, Pyruvate Ferredoxin,Oxidoreductase, Pyruvate-Ferredoxin,Synthase, Pyruvate,Synthetase, Pyruvate

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