Activation of nitrofurazone by azoreductases: multiple activities in one enzyme

Sci Rep. 2011:1:63. doi: 10.1038/srep00063. Epub 2011 Aug 12.

Abstract

Azoreductases are well known for azo pro-drug activation by gut flora. We show that azoreductases have a wider role in drug metabolism than previously thought as they can also reduce and hence activate nitrofurazone. Nitrofurazone, a nitroaromatic drug, is a broad spectrum antibiotic which has until now been considered as activated in bacteria by nitroreductases. The structure of the azoreductase with nitrofurazone bound was solved at 2.08 Å and shows nitrofurazone in an active conformation. Based on the structural information, the kinetics and stoichiometry of nitrofurazone reduction by azoreductase from P. aeruginosa, we propose a mechanism of activation which accounts for the ability of azoreductases to reduce both azo and nitroaromatic drugs. This mode of activation can explain the cytotoxic side-effects of nitrofurazone through human azoreductase homologues.

MeSH terms

  • Biotransformation
  • Models, Molecular
  • NADH, NADPH Oxidoreductases / chemistry
  • NADH, NADPH Oxidoreductases / metabolism*
  • Nitrofurazone / chemistry
  • Nitrofurazone / pharmacokinetics*
  • Nitroreductases

Substances

  • NADH, NADPH Oxidoreductases
  • Nitroreductases
  • azoreductase
  • Nitrofurazone