New neurogenic lipoic-based hybrids as innovative Alzheimer's drugs with σ-1 agonism and β-secretase inhibition

Future Med Chem. 2016 Jul;8(11):1191-207. doi: 10.4155/fmc-2016-0036. Epub 2016 Jul 12.

Abstract

Background: Neurogenic agents emerge as innovative drugs for the treatment of Alzheimer's disease (AD), whose pathological complexity suggests strengthening research in the multi-target directed ligands strategy.

Results: By combining the lipoic acid structure with N-benzylpiperidine or N,N-dibenzyl(N-methyl)amine fragments, new multi-target directed ligands were obtained that act at three relevant targets in AD: σ-1 receptor (σ1R), β-secretase-1 (BACE1) and acetylcholinesterase (AChE). Moreover, they show potent neurogenic properties, good antioxidant capacity and favorable CNS permeability. Molecular modeling studies on AChE, σ1R and BACE1 highlight relevant drug-protein interactions that may contribute to the development of new disease-modifying drugs.

Conclusion: New lipoic-based σ1 agonists endowed with neurogenic, antioxidant, cholinergic and amyloid β-peptide-reducing properties have been discovered for the potential treatment of AD.

Keywords: AChE; AD; Alzheimer's disease; BACE1; N,N-dibenzyl(N-methyl)amine; N-benzylpiperidine; acetylcholinesterase; lipoic acid; multi-target directed ligands; neurogenic properties; β-secretase-1; σ-1 receptor; σ1R.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetylcholinesterase / metabolism
  • Alzheimer Disease / drug therapy*
  • Alzheimer Disease / metabolism
  • Amyloid Precursor Protein Secretases / antagonists & inhibitors*
  • Amyloid Precursor Protein Secretases / metabolism
  • Antioxidants / chemistry
  • Antioxidants / pharmacology
  • Aspartic Acid Endopeptidases / antagonists & inhibitors*
  • Aspartic Acid Endopeptidases / metabolism
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology*
  • Humans
  • Lipids / chemistry
  • Lipids / pharmacology*
  • Molecular Structure
  • Neuroprotective Agents / chemistry
  • Neuroprotective Agents / pharmacology*
  • Receptors, sigma / agonists*
  • Sigma-1 Receptor

Substances

  • Antioxidants
  • Enzyme Inhibitors
  • Lipids
  • Neuroprotective Agents
  • Receptors, sigma
  • Acetylcholinesterase
  • Amyloid Precursor Protein Secretases
  • Aspartic Acid Endopeptidases
  • BACE1 protein, human