Discovery of styrylaniline derivatives as novel alpha-synuclein aggregates ligands

Eur J Med Chem. 2021 Dec 15:226:113887. doi: 10.1016/j.ejmech.2021.113887. Epub 2021 Oct 2.

Abstract

Parkinson's disease (PD) is the second most common neurodegenerative disorder. Early diagnosis is the key to treatment but is still a great challenge in the clinic now. The discovery of alpha-synuclein (α-syn) aggregates ligands has become an attractive strategy to meet the early diagnosis of PD. Herein, we designed and synthesized a series of styrylaniline derivatives as novel α-syn aggregates ligands. Several compounds displayed good potency to α-syn aggregates with Kd values less than 0.1 μM. The docking study revealed that the hydrogen bonds and cation-pi interaction between ligands and α-syn aggregates would be crucial for the activity. The representative compound 7-16 not only detected α-syn aggregates in both SH-SY5Y cells and brain tissues prepared from two kinds of α-syn preformed-fibrils-injected mice models but also showed good blood-brain barrier penetration characteristics in vivo with a brain/plasma ratio over 1.0, which demonstrates its potential as a lead compound for further development of in vivo imaging agents.

Keywords: Blood-brain barrier; Early diagnosis; Parkinson's disease; Styrylphenyl benzamides; α-synuclein ligand.

MeSH terms

  • Aniline Compounds / chemical synthesis
  • Aniline Compounds / chemistry
  • Aniline Compounds / pharmacology*
  • Animals
  • Cell Line, Tumor
  • Dose-Response Relationship, Drug
  • Drug Discovery*
  • Humans
  • Ligands
  • Male
  • Mice
  • Mice, Inbred C57BL
  • Molecular Docking Simulation
  • Molecular Structure
  • Parkinson Disease / diagnosis
  • Parkinson Disease / drug therapy*
  • Parkinson Disease / metabolism
  • Protein Aggregates / drug effects
  • Rats
  • Rats, Sprague-Dawley
  • Structure-Activity Relationship
  • alpha-Synuclein / antagonists & inhibitors*
  • alpha-Synuclein / metabolism

Substances

  • Aniline Compounds
  • Ligands
  • Protein Aggregates
  • SNCA protein, human
  • alpha-Synuclein