Novel anti-Alzheimer phenol-lipoyl hybrids: Synthesis, physico-chemical characterization, and biological evaluation

Eur J Med Chem. 2020 Jan 15:186:111880. doi: 10.1016/j.ejmech.2019.111880. Epub 2019 Nov 12.

Abstract

To date, drugs that hit a single target are inadequate for the treatment of neurodegenerative diseases, such as Alzheimer's or Parkinson's diseases. The development of multitarget ligands, able to interact with the different pathways involved in the progession of these disorders, represents a great challenge for medicinal chemists. In this context, we report here the synthesis and biological evaluation of phenol-lipoyl hybrids (SV1-13), obtained via a linking strategy, to take advantage of the synergistic effect due to the antioxidant portions and anti-amyloid properties of the single constituents present in the hybrid molecule. Biological results showed that SV5 and SV10 possessed the best protective activity against Aβ1-42 induced neurotoxicity in differentiated SH-SY5Y cells. SV9 and SV10 showed remarkable antioxidant properties due to their ability to counteract the damage caused by H2O2 in SHSY-5Y-treated cells. Hovewer, SV5, showing moderate antioxidant and good neuroprotective activities, resulted the best candidate for further experiments since it also resulted stable both simulated and plasma fluids.

Keywords: Alzheimer’s disease; Hybrid; Lipoic acid; Polyphenol.

MeSH terms

  • Alzheimer Disease / drug therapy*
  • Alzheimer Disease / metabolism
  • Amyloid beta-Peptides / antagonists & inhibitors*
  • Amyloid beta-Peptides / metabolism
  • Antioxidants / chemical synthesis
  • Antioxidants / chemistry
  • Antioxidants / pharmacology*
  • Cell Proliferation / drug effects
  • Dose-Response Relationship, Drug
  • Humans
  • Molecular Structure
  • Neuroprotective Agents / chemical synthesis
  • Neuroprotective Agents / chemistry
  • Neuroprotective Agents / pharmacology*
  • Peptide Fragments / antagonists & inhibitors*
  • Peptide Fragments / metabolism
  • Phenols / chemical synthesis
  • Phenols / chemistry
  • Phenols / pharmacology*
  • Protein Aggregates / drug effects
  • Structure-Activity Relationship
  • Thioctic Acid / chemical synthesis
  • Thioctic Acid / chemistry
  • Thioctic Acid / pharmacology*
  • Tumor Cells, Cultured

Substances

  • Amyloid beta-Peptides
  • Antioxidants
  • Neuroprotective Agents
  • Peptide Fragments
  • Phenols
  • Protein Aggregates
  • amyloid beta-protein (1-42)
  • Thioctic Acid