Peptidomimetic β-Secretase Inhibitors Comprising a Sequence of Amyloid-β Peptide for Alzheimer's Disease

J Med Chem. 2015 Jul 23;58(14):5408-18. doi: 10.1021/acs.jmedchem.5b00658. Epub 2015 Jul 1.

Abstract

Alzheimer's disease is a grave social problem in an aging population. A major problem is the passage of drugs through the blood-brain barrier. This work tests the hypothesis that the conjugation of peptidomimetic β-secretase inhibitors with a fragment of amyloid-β peptide facilitates entrance into the central nervous system. HVR-3 (compound 4), one of the conjugation products, was found to be as potent as OM00-3, a known peptidomimetic inhibitor, 4-fold more selective toward β-secretase 1 in relation to β-secretase 2 and 3-fold more resistant to in vitro metabolization in human serum. Its intravenous administration to mice and Wistar rats generated an active metabolite recovered from the rodent's brains.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acylation
  • Alzheimer Disease / drug therapy*
  • Amino Acid Sequence
  • Amyloid Precursor Protein Secretases / antagonists & inhibitors*
  • Amyloid beta-Peptides / chemistry*
  • Animals
  • Brain / metabolism
  • Caco-2 Cells
  • Cell Survival / drug effects
  • Drug Design
  • Female
  • Humans
  • Male
  • Mice
  • Molecular Sequence Data
  • Peptide Fragments / chemistry
  • Peptidomimetics / chemistry*
  • Peptidomimetics / pharmacokinetics
  • Peptidomimetics / pharmacology*
  • Peptidomimetics / therapeutic use
  • Protease Inhibitors / chemistry*
  • Protease Inhibitors / pharmacokinetics
  • Protease Inhibitors / pharmacology*
  • Protease Inhibitors / therapeutic use
  • Rats
  • Structure-Activity Relationship

Substances

  • Amyloid beta-Peptides
  • Peptide Fragments
  • Peptidomimetics
  • Protease Inhibitors
  • Amyloid Precursor Protein Secretases