Inhibitors for human glutaminyl cyclase by structure based design and bioisosteric replacement

J Med Chem. 2009 Nov 26;52(22):7069-80. doi: 10.1021/jm900969p.

Abstract

The inhibition of human glutaminyl cyclase (hQC) has come into focus as a new potential approach for the treatment of Alzheimer's disease. The hallmark of this principle is the prevention of the formation of Abeta(3,11(pE)-40,42), as these Abeta-species were shown to be of elevated neurotoxicity and likely to act as a seeding core leading to an accelerated formation of Abeta-oligomers and fibrils. Starting from 1-(3-(1H-imidazol-1-yl)propyl)-3-(3,4-dimethoxyphenyl)thiourea, bioisosteric replacements led to the development of new classes of inhibitors. The optimization of the metal-binding group was achieved by homology modeling and afforded a first insight into the probable binding mode of the inhibitors in the hQC active site. The efficacy assessment of the hQC inhibitors was performed in cell culture, directly monitoring the inhibition of Abeta(3,11(pE)-40,42) formation.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aminoacyltransferases / antagonists & inhibitors*
  • Aminoacyltransferases / chemistry
  • Amyloid beta-Peptides / antagonists & inhibitors
  • Amyloid beta-Peptides / chemistry
  • Amyloid beta-Peptides / metabolism
  • Catalytic Domain
  • Cell Line
  • Drug Design*
  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / chemistry*
  • Enzyme Inhibitors / pharmacology*
  • Humans
  • Models, Molecular
  • Pyrrolidonecarboxylic Acid / metabolism
  • Structure-Activity Relationship
  • Thiourea / chemistry

Substances

  • Amyloid beta-Peptides
  • Enzyme Inhibitors
  • Aminoacyltransferases
  • glutaminyl-peptide cyclotransferase
  • Thiourea
  • Pyrrolidonecarboxylic Acid