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1 Central European Journal of Energetic Materials

1 2006

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Reduction of Nitroaromatic Explosives by Oxygen-Insensitive NAD(P)H:Nitroreductases: Implications for their Cytotoxicity and Biodegradation

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Misevičiene L. , Nivinskas H. , Anusevičius Z. , Čenas N. , Nemeikaite-Čeniene A. , Maldutis E. , Harris R. J. , Scrutton N. S.

tom Vol. 3, nr 4

89-101

Nitroaromatic explosives are toxic and mutagenic to humans and other mammalian species. The first step(s) in the biodegradation/bioremediation of the explosive residues in soil or groundwater is their reduction by bacterial oxygeninsensitive nitroreductases to the relatively stable metabolites. Here we analyze the quantitative structure-activity relationships in the reduction of nitroaromatic explosives and model nitroaromatic compounds by mammalian DT-diaphorase (NQO1) and Enterobacter cloacae NAD(P)H:nitroreductase (NR), which performs the four-electron reduction of nitrogroups to corresponding hydroxylamines, and by Enterobacter cloacae PB2 NADPH: pentaerythritol tetranitrate reductase (PETNR), which performs nitroreduction and reduction of benzene ring with the formation of hydride-Meisenheimer adducts. Our data show that in all the cases the reduction rate of nitroaromatics mainly depends on the energetics of the charge transfer.