Reduction of nitroaromatic compounds by NAD(P)H:quinone oxidoreductase (NQO1): the role of electron-accepting potency and structural parameters in the substrate specificity

• Authors: Lina Misevičienė , Žilvinas Anusevičius , Jonas Šarlauskas , Narimantas Čėnas
• Languages of publication: EN

Abstracts

EN

We aimed to elucidate the role of electronic and structural parameters of nitroaromatic compounds in their two-electron reduction by NAD(P)H:quinone oxidoreductase (NQO1, DT-diaphorase, EC 1.6.99.2). The multiparameter regression analysis shows that the reactivity of nitroaromatic compounds (n = 38) increases with an increase in their single-electron reduction potential and the torsion angle between nitrogroup(s) and the aromatic ring. The binding efficiency of nitroaromatics in the active center of NQO1 exerted a less evident role in their reactivity. The reduction of nitroaromatics is characterized by more positive entropies of activation than the reduction of quinones. This points to a less efficient electronic coupling of nitroaromatics with the reduced isoalloxazine ring of FAD, and may explain their lower reactivity as compared to quinones. Another important but poorly understood factor enhancing the reactivity of nitroaromatics is their ability to bind at the dicumarol/quinone binding site in the active center of NQO1.

Keywords

EN

reduction potential; DT-diaphorase; nitroaromatic compounds; reduction mechanism; explosives

• Publisher: Polish Biochemical Society
• Journal: Acta Biochimica Polonica
• Year: 2006
• Volume: 53
• Issue: 3
• Pages: 569-576

Dates

published

2006

received

2006-03-01

revised

2006-04-14

accepted

2006-06-14

(unknown)

2006-08-21

Contributors

author

Lina Misevičienė

• Institute of Biochemistry, Vilnius, Lithuania

author

Žilvinas Anusevičius

• Institute of Biochemistry, Vilnius, Lithuania

author

Jonas Šarlauskas

• Institute of Biochemistry, Vilnius, Lithuania

author

Narimantas Čėnas

• Institute of Biochemistry, Vilnius, Lithuania

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