Inhibiting and reversing amyloid-β peptide (1-40) fibril formation with gramicidin S and engineered analogues

Chemistry. 2013 Dec 16;19(51):17338-48. doi: 10.1002/chem.201301535. Epub 2013 Nov 11.

Abstract

In Alzheimer's disease, amyloid-β (Aβ) peptides aggregate into extracellular fibrillar deposits. Although these deposits may not be the prime cause of the neurodegeneration that characterizes this disease, inhibition or dissolution of amyloid fibril formation by Aβ peptides is likely to affect its development. ThT fluorescence measurements and AFM images showed that the natural antibiotic gramicidin S significantly inhibited Aβ amyloid formation in vitro and could dissolve amyloids that had formed in the absence of the antibiotic. In silico docking suggested that gramicidin S, a cyclic decapeptide that adopts a β-sheet conformation, binds to the Aβ peptide hairpin-stacked fibril through β-sheet interactions. This may explain why gramicidin S reduces fibril formation. Analogues of gramicidin S were also tested. An analogue with a potency that was four-times higher than that of the natural product was identified.

Keywords: Alzheimer’s disease; amyloid-beta peptides; antibiotics; fibrillization; structure-activity relationships.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amyloid beta-Peptides / antagonists & inhibitors
  • Amyloid beta-Peptides / metabolism*
  • Benzothiazoles
  • Gramicidin / chemistry
  • Gramicidin / metabolism*
  • Hydrogen Bonding
  • Hydrophobic and Hydrophilic Interactions
  • Microscopy, Atomic Force
  • Microscopy, Electron, Scanning
  • Peptide Fragments / antagonists & inhibitors
  • Peptide Fragments / metabolism*
  • Protein Binding
  • Protein Structure, Secondary
  • Structure-Activity Relationship
  • Thiazoles / chemistry

Substances

  • Amyloid beta-Peptides
  • Benzothiazoles
  • Peptide Fragments
  • Thiazoles
  • amyloid beta-protein (1-40)
  • Gramicidin
  • thioflavin T