Synthesis and structure-activity relationship of furoquinolinediones as inhibitors of Tyrosyl-DNA phosphodiesterase 2 (TDP2)

Eur J Med Chem. 2018 May 10:151:777-796. doi: 10.1016/j.ejmech.2018.04.024. Epub 2018 Apr 12.

Abstract

Tyrosyl-DNA phosphodiesterase 2 (TDP2) is a recently discovered enzyme specifically repairing topoisomerase II (TOP2)-mediated DNA damage. It has been shown that inhibition of TDP2 synergize with TOP2 inhibitors. Herein, we report the discovery of the furoquinolinedione chemotype as a suitable skeleton for the development of selective TDP2 inhibitors. Compound 1 was identified as a TDP2 inhibitor as a result of screening our in-house compound library for compounds selective for TDP2 vs. TDP1. Further SAR studies provide several selective TDP2 inhibitors at low-micromolar range. The most potent compound 74 shows inhibitory activity with IC50 of 1.9 and 2.1 μM against recombinant TDP2 and TDP2 in whole cell extracts (WCE), respectively.

Keywords: DNA repair; Furoquinolinedione; Inhibitor; Topoisomerase; Tyrosyl-DNA phosphodiesterase.

MeSH terms

  • Animals
  • Cell Line
  • Chickens
  • DNA-Binding Proteins
  • Humans
  • Molecular Docking Simulation
  • Nuclear Proteins / antagonists & inhibitors*
  • Nuclear Proteins / metabolism
  • Phosphodiesterase Inhibitors / chemical synthesis
  • Phosphodiesterase Inhibitors / chemistry*
  • Phosphodiesterase Inhibitors / pharmacology*
  • Phosphoric Diester Hydrolases
  • Quinolines / chemical synthesis
  • Quinolines / chemistry*
  • Quinolines / pharmacology*
  • Recombinant Proteins / metabolism
  • Structure-Activity Relationship
  • Transcription Factors / antagonists & inhibitors*
  • Transcription Factors / metabolism

Substances

  • DNA-Binding Proteins
  • Nuclear Proteins
  • Phosphodiesterase Inhibitors
  • Quinolines
  • Recombinant Proteins
  • Transcription Factors
  • Phosphoric Diester Hydrolases
  • TDP2 protein, human