Piperidine-4-carboxamide as a new scaffold for designing secretory glutaminyl cyclase inhibitors

Int J Biol Macromol. 2021 Feb 15:170:415-423. doi: 10.1016/j.ijbiomac.2020.12.118. Epub 2020 Dec 27.

Abstract

Alzheimer's disease (AD), a common chronic neurodegenerative disease, has become a major public health concern. Despite years of research, therapeutics for AD are limited. Overexpression of secretory glutaminyl cyclase (sQC) in AD brain leads to the formation of a highly neurotoxic pyroglutamate variant of amyloid beta, pGlu-Aβ, which acts as a potential seed for the aggregation of full length Aβ. Preventing the formation of pGlu-Aβ through inhibition of sQC has become an attractive disease-modifying therapy in AD. In this current study, through a pharmacophore assisted high throughput virtual screening, we report a novel sQC inhibitor (Cpd-41) with a piperidine-4-carboxamide moiety (IC50 = 34 μM). Systematic molecular docking, MD simulations and X-ray crystallographic analysis provided atomistic details of the binding of Cpd-41 in the active site of sQC. The unique mode of binding and moderate toxicity of Cpd-41 make this molecule an attractive candidate for designing high affinity sQC inhibitors.

Keywords: Alzheimer's disease; Amide inhibitors; Glutaminyl cyclase; Pyroglutamate.

MeSH terms

  • Alzheimer Disease / drug therapy
  • Aminoacyltransferases / antagonists & inhibitors*
  • Amyloid beta-Peptides / metabolism
  • Brain / drug effects
  • Brain / metabolism
  • Cell Line, Tumor
  • Humans
  • Molecular Docking Simulation
  • Piperidines / pharmacology*
  • Pyrrolidonecarboxylic Acid / metabolism

Substances

  • Amyloid beta-Peptides
  • Piperidines
  • piperidine-4-carboxamide
  • Aminoacyltransferases
  • glutaminyl-peptide cyclotransferase
  • Pyrrolidonecarboxylic Acid