Old and new inhibitors of quinone reductase 2

Chem Biol Interact. 2010 Jul 30;186(2):103-9. doi: 10.1016/j.cbi.2010.04.006. Epub 2010 May 4.

Abstract

Quinone reductase 2 is a cytosolic enzyme which catalyses the reduction of quinones, such as menadione and coenzymes Q. Despite a relatively close sequence-based resemblance to NAD(P)H:quinone oxidoreductase 1 (QR1), it has many different features. QR2 is the third melatonin binding site (MT3). It is inhibited in the micromolar range by melatonin, and does not accept conventional phosphorylated nicotinamides as hydride donors. QR2 has a powerful capacity to activate quinones leading to unexpected toxicity situations. In the present paper, we report the characterization of three QR2 modulators: melatonin, resveratrol and S29434. The latter compound inhibits QR2 activity with an IC(50) in the low nanomolar range. The potency of the modulators ranged as follows, from the least to the most potent: melatonin<resveratrol<S29434. These molecular tools might permit to explore and better understand the relationship existing between QR2 catalytic activity and the various pathological situations in which QR2 has a key role.

MeSH terms

  • Animals
  • Base Sequence
  • DNA Primers / genetics
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology*
  • Furans / chemistry
  • Furans / pharmacology
  • Humans
  • In Vitro Techniques
  • Kinetics
  • Melatonin / pharmacology
  • Pyridines / chemistry
  • Pyridines / pharmacology*
  • Pyrrolizidine Alkaloids / chemistry
  • Pyrrolizidine Alkaloids / pharmacology*
  • Quinone Reductases / antagonists & inhibitors*
  • Quinone Reductases / genetics
  • Quinone Reductases / metabolism
  • Receptors, Melatonin / metabolism
  • Recombinant Proteins / antagonists & inhibitors
  • Recombinant Proteins / genetics
  • Recombinant Proteins / metabolism
  • Resveratrol
  • Spodoptera
  • Stilbenes / pharmacology
  • Substrate Specificity

Substances

  • DNA Primers
  • Enzyme Inhibitors
  • Furans
  • N-(2-(2-methoxy-6H-dipyrido(2,3-a-3,2-e)pyrrolizin-11-yl)ethyl)-2-furamide
  • Pyridines
  • Pyrrolizidine Alkaloids
  • Receptors, Melatonin
  • Recombinant Proteins
  • Stilbenes
  • NRH - quinone oxidoreductase2
  • Quinone Reductases
  • Melatonin
  • Resveratrol