A novel bis-furan scaffold for transthyretin stabilization and amyloid inhibition

Eur J Med Chem. 2016 Oct 4:121:823-840. doi: 10.1016/j.ejmech.2016.02.074. Epub 2016 Mar 3.

Abstract

The design and synthesis of a novel bis-furan scaffold tailored for high efficiency at inhibiting transthyretin amyloid formation is reported. In vitro results show that the discovered compounds are more efficient inhibitors of amyloid formation than tafamidis, a drug currently used in the treatment of familial amyloid polyneuropathy (FAP), despite their lower molecular weight and lipophilicity. Moreover, ex vivo experiments with the strongest inhibitor in the series, conducted in human blood plasma from normal and FAP Val30Met-transthyretin carriers, disclose remarkable affinity and selectivity profiles. The promises and challenges facing further development of this compound are discussed under the light of increasing evidence implicating transthyretin stability as a key factor not only in transthyretin amyloidoses and several associated co-morbidities, but also in Alzheimer's disease.

Keywords: Amyloid; Bis-furans; Lead discovery; Neurodegeneration; Transthyretin.

MeSH terms

  • Amyloid / chemistry*
  • Amyloid / metabolism
  • Drug Design*
  • Furans / chemistry*
  • Furans / metabolism
  • Furans / pharmacology*
  • Hep G2 Cells
  • Humans
  • Inhibitory Concentration 50
  • Molecular Docking Simulation
  • Prealbumin / chemistry*
  • Prealbumin / metabolism
  • Protein Aggregates / drug effects
  • Protein Conformation
  • Protein Stability / drug effects

Substances

  • Amyloid
  • Furans
  • Prealbumin
  • Protein Aggregates