Design, synthesis and evaluation of coumarin-pargyline hybrids as novel dual inhibitors of monoamine oxidases and amyloid-β aggregation for the treatment of Alzheimer's disease

Eur J Med Chem. 2017 Sep 29:138:715-728. doi: 10.1016/j.ejmech.2017.07.008. Epub 2017 Jul 8.

Abstract

A series of coumarin-pargyline hybrids (4a-x) have been designed, synthesized and evaluated as novel dual inhibitors of Alzheimer's disease (AD). Most of the compounds exhibited a potent ability to inhibit amyloid-β (Aβ) aggregation and monoamine oxidases. In particular, compound 4x exhibited remarkable inhibitory activities against monoamine oxidases (IC50, 0.027 ± 0.004 μM for MAO-B; 3.275 ± 0.040 μM for MAO-A) and Aβ1-42 aggregation (54.0 ± 1.1%, 25 μM). Moreover, compound 4x showed low toxicity according to in vitro cell toxicity test. The results of the parallel artificial membrane permeability assay for blood-brain barrier indicated that compound 4x would be potent to cross the blood-brain barrier. Collectively, these findings demonstrate that compound 4x was an effective and promising candidate for AD therapy.

Keywords: Alzheimer's disease; Aβ(1-42) aggregation; Coumarin; Monoamine oxidases; Pargyline.

MeSH terms

  • Alzheimer Disease / drug therapy*
  • Alzheimer Disease / metabolism
  • Amyloid beta-Peptides / antagonists & inhibitors*
  • Amyloid beta-Peptides / metabolism
  • Animals
  • Cell Survival / drug effects
  • Coumarins / chemistry
  • Coumarins / pharmacology*
  • Dose-Response Relationship, Drug
  • Drug Design
  • Humans
  • Male
  • Mice
  • Mice, Inbred Strains
  • Molecular Structure
  • Monoamine Oxidase / metabolism*
  • Monoamine Oxidase Inhibitors / chemical synthesis
  • Monoamine Oxidase Inhibitors / chemistry
  • Monoamine Oxidase Inhibitors / pharmacology*
  • PC12 Cells
  • Pargyline / chemistry
  • Pargyline / pharmacology*
  • Protein Aggregates / drug effects
  • Rats
  • Structure-Activity Relationship

Substances

  • Amyloid beta-Peptides
  • Coumarins
  • Monoamine Oxidase Inhibitors
  • Protein Aggregates
  • Pargyline
  • coumarin
  • Monoamine Oxidase