5-Aroylindoles Act as Selective Histone Deacetylase 6 Inhibitors Ameliorating Alzheimer's Disease Phenotypes

J Med Chem. 2018 Aug 23;61(16):7087-7102. doi: 10.1021/acs.jmedchem.8b00151. Epub 2018 Aug 9.

Abstract

This paper reports the development of a series of 5-aroylindolyl-substituted hydroxamic acids. N-Hydroxy-4-((5-(4-methoxybenzoyl)-1 H-indol-1-yl)methyl)benzamide (6) has potent inhibitory selectivity against histone deacetylase 6 (HDAC6) with an IC50 value of 3.92 nM. It decreases not only the level of phosphorylation of tau proteins but also the aggregation of tau proteins. Compound 6 also shows neuroprotective activity by triggering ubiquitination. In animal models, compound 6 is able to ameliorate the impaired learning and memory, and it crosses the blood-brain barrier after oral administration. Compound 6 can be developed as a potential treatment for Alzheimer's disease in the future.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alzheimer Disease / drug therapy
  • Animals
  • Binding Sites
  • Blood-Brain Barrier / drug effects
  • Cell Line
  • Disease Models, Animal
  • Female
  • Histone Deacetylase 6 / antagonists & inhibitors*
  • Histone Deacetylase 6 / chemistry
  • Histone Deacetylase 6 / metabolism
  • Histone Deacetylase Inhibitors / chemical synthesis
  • Histone Deacetylase Inhibitors / chemistry*
  • Histone Deacetylase Inhibitors / pharmacology*
  • Humans
  • Hydroxamic Acids / chemistry
  • Indoles / chemistry*
  • Indoles / pharmacology
  • Male
  • Memory and Learning Tests
  • Mice, Transgenic
  • Molecular Docking Simulation
  • Neuroprotective Agents / chemistry
  • Neuroprotective Agents / pharmacology*
  • Phosphorylation / drug effects
  • Rats, Sprague-Dawley
  • Rats, Wistar
  • Ubiquitination / drug effects
  • tau Proteins / metabolism

Substances

  • Histone Deacetylase Inhibitors
  • Hydroxamic Acids
  • Indoles
  • Neuroprotective Agents
  • tau Proteins
  • HDAC6 protein, human
  • Histone Deacetylase 6