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

Acta Biochimica Polonica

Volumn 53, Issue 3, 2006, Pages 569-576

  Misevičiene, Lina ^a   Anusevičius, Žilvinas ^a   Šarlauskas, Jonas ^a   Čenas, Narimantas ^a  

^a Institute of Biochemistry   (Lithuania)

Author keywords

Dt diaphorase; Explosives; Nitroaromatic compounds; Reduction mechanism; Reduction potential

Indexed keywords

EID: 33749832117     PISSN: 0001527X     EISSN: 1734154X     Source Type: Journal    
DOI: 10.18388/abp.2006_3329     Document Type: Article

References (27)

1. Agrawal JP, Surve RN, Mehilal, Sonawase SH (2000) Some aromatic nitrate esters: synthesis, structural aspects, thermal and explosive properties. J Hazard Mater 77A: 11-31.
2. Anusevičius Ž, Šarlauskas J, Čėnas N (2002) Two-electron reduction of quinones by rat liver NAD(P)H:quinone oxidoreductase: quantitative structure-activity relationships. Arch Biochem Biophys 404: 254-262.
3. Arlt VM, Stiborova M, Henderson CJ, Osborne MR, Bieler CA, Frei E, Martinek V, Sopko B, Wolf CR, Schmeiser HH, Phillips DH (2005) Environmental pollutant and potent mutagen 3-nitrobenzanthrone forms DNA adducts after reduction by NAD(P)H:quinone oxidoreductase and conjugation by acetyltransferases and sulfotransferases in human hepatic cytosol. Cancer Res 65: 2644-2652.
4. Bianchet MA, Faig M, Amzel LM (2004) Structure and mechanism of NAD[P]H:quinone acceptor oxidoreductases. Methods Enzymol 382B: 144-174.
5. Čėnas N, Nemeikaitė-Čėnienė A, Sergedienė E, Nivinskas H, Anusevičius Ž, Šarlauskas J (2001) Quantitative structure-activity relationships in enzymatic single-electron reduction of nitroaromatic explosives: implications for their cytotoxicity. Biochim Biophys Acta 1528: 31-38.
6. Čėnas N, Anusevičius Ž, Nivinskas H, Misevičienė L, Šarlauskas, J (2004) Structure-activity relationships in two-electron reduction of quinones. Methods Enzymol 382B: 258-277.
7. Chen S, Wu K, Zhang D, Sherman M, Knox R, Yang CS (1999) Molecular characterization of binding of substrates and inhibitors to DT-diaphorase: combined approach involving site-directed mutagenesis, inhibitor-binding analysis, and computer modeling. Mol Pharmacol 58: 272-278.
8. DiFrancesco AM, Ward TH, Butler J (2004) Diaziridinyl-benzoquinones. Methods Enzymol 382B: 174-193.
9. Knox RJ, Chen S (2004) Quinone reductase-mediated nitro-reduction: clinical applications. Methods Enzymol 382B: 194-221.
10. m. Bioorg Chem 30: 211-213.
11. Mehilal, Sikder AK, Sinha RK, Gandhe BR (2003) Cost-effective synthesis of 5,7-diamino-4,6-dinitrobenzofuroxan (CL-14) and its evaluation in plastic bonded explosives. J Hazard Materials 102A: 137-145.
12. Miškinienė V, Sergedienė E, Nemeikaitė A, Segura-Aguilar J, Čėnas N (1999) Role of redox cycling and activation by DT-diaphorase in the cytotoxicity of 5-(aziridin-1-yl)-2,4- dinitro-benzamide (CB-1954) and its analogs. Cancer Lett 146: 217-222.
13. Nemeikaitė-Čėnienė A, Šarlauskas J, Misevičienė L, Anusevičius Ž, Marozienė A, Čėnas N (2004) Enzymatic redox reactions of the explosive 4,6-dinitrobenzofuroxan (DNBF): implications for its toxic action. Acta Biochim Polon 51: 1081-1086.
14. Nivinskas H, Koder RL, Anusevičius Ž, Šarlauskas J, Miller A-F, Čėnas N (2001) Quantitative structure-activity relationships in two-electron reduction of nitroaromatic compounds by Enterobacter cloacae NAD(P)H:nitroreductase. Arch Biochem Biophys 385: 170-178.
15. Orna VM, Mason RP (1989) Correlation of kinetic parameters of nitroreductase enzymes with redox properties of nitroaromatic compounds. J Biol Chem 264: 12379-12384.
16. Prochaska HJ (1988) Purification and crystallization of rat liver NAD(P)H:(quinone-acceptor) oxidoreductase by cibacron blue affinity chromatography: identification of a new and potent inhibitor. Arch Biochem Biophys 267: 529-538.
17. Race PR, Lovering AL, Green RM, Ossor A, White SA, Searle PF, Wrighton CJ, Hyde EI (2005) Structural and mechanistic studies of Escherichia coli nitroreductase with the antibiotic nitrofurazone. Reversed binding orientations in different redox states of the enzyme. J Biol Chem 280: 13256-13264.
18. Riefler RG, Smets BF (2000) Enzymatic reduction of 2,4,6-trinitrotoluene and related nitroarenes: kinetics linked to one-electron reduction potentials. Environ Sci Technol 34: 3900-3906.
19. Ross D, Kepa JK, Winski SL, Beall HD, Anwar A, Siegel D (2000) NAD(P)H:quinone oxidoreductase 1 (NQO1): chemoprotection, bioactivation, gene regulation and genetic polymorphisms. Chem-Biol Interact 129: 77-97.
20. Šarlauskas J, Dičkancaitė E, Nemeikaitė A, Anusevičius Ž, Nivinskas H, Segura-Aguilar J, Čėnas N (1997) Nitrobenzimidazoles as substrates for DT-diaphorase and redox cycling compounds: their enzymatic reactions and cytotoxicity. Arch Biochem Biophys 346: 219-229.
21. Šarlauskas J, Nemeikaitė-Čėnienė A, Anusevičius Ž, Misevičienė L, Martinez-Julvez M, Medina M, Gomez-Moreno C, Čėnas N (2004a) Flavoenzyme-catalyzed redox cycling of hydroxylamino- and amino metabolites of 2,4,6-trinitrotoluene: implications for their cytotoxicity. Arch Biochem Biophys 425: 184-192.
22. Šarlauskas J, Nemeikaitė-Čėnienė A, Anusevičius Ž, Misevičienė L, Marozienė A, Markevičius A, Čėnas N (2004b) Enzymatic redox properties of novel nitrotriazole explosives. Implications for their cytotoxicity. Z Naturforsch 59c: 399-404.
23. 7) of nitroaromatic compounds according to the kinetics of their single-electron reduction by flavoenzymes. Chemija (Vilnius) 17: 31-37.
24. Skelly JV, Sanderson MR, Suter DA, Bauman U, Read MA, Gregory DSJ, Bennett M, Hobbs SM, Neidle S (1999) Crystal structure of human DT-diaphorase: a model for interaction with the cytotoxic prodrug 5-(aziridin-1-yl)-2,4- dinitrobenzamide (CB1954) J Med Chem 42: 4325-4330.
25. Tedeschi G, Chen S, Massey V (1995) DT-diaphorase. Redox potential, steady-state, and rapid reaction studies. J Biol Chem 270: 1198-1204.
26. Wardman P (1989) Reduction potentials of one-electron couples involving free radicals in aqueous solutions. J Phys Chem Ref Data 18: 1637-1755.
27. Zuman P, Fijalek Z, Dumanovic D, Suznjevic D (1992) Polarographic and electrochemical studies of some aromatic and heterocyclic nitro-compounds. 1. General mechanistic aspects. Electroanalysis 4: 783-794.