Sustainable Drug Discovery of Multi-Target-Directed Ligands for Alzheimer's Disease

J Med Chem. 2021 Apr 22;64(8):4972-4990. doi: 10.1021/acs.jmedchem.1c00048. Epub 2021 Apr 8.

Abstract

The multifactorial nature of Alzheimer's disease (AD) is a reason for the lack of effective drugs as well as a basis for the development of "multi-target-directed ligands" (MTDLs). As cases increase in developing countries, there is a need of new drugs that are not only effective but also accessible. With this motivation, we report the first sustainable MTDLs, derived from cashew nutshell liquid (CNSL), an inexpensive food waste with anti-inflammatory properties. We applied a framework combination of functionalized CNSL components and well-established acetylcholinesterase (AChE)/butyrylcholinesterase (BChE) tacrine templates. MTDLs were selected based on hepatic, neuronal, and microglial cell toxicity. Enzymatic studies disclosed potent and selective AChE/BChE inhibitors (5, 6, and 12), with subnanomolar activities. The X-ray crystal structure of 5 complexed with BChE allowed rationalizing the observed activity (0.0352 nM). Investigation in BV-2 microglial cells revealed antineuroinflammatory and neuroprotective activities for 5 and 6 (already at 0.01 μM), confirming the design rationale.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetylcholinesterase / chemistry
  • Acetylcholinesterase / metabolism
  • Alzheimer Disease / drug therapy
  • Alzheimer Disease / pathology
  • Anacardium / chemistry
  • Anacardium / metabolism
  • Binding Sites
  • Butyrylcholinesterase / chemistry
  • Butyrylcholinesterase / metabolism
  • Catalytic Domain
  • Cell Line
  • Cell Survival / drug effects
  • Cytokines / metabolism
  • Drug Design
  • Humans
  • Ligands*
  • Lipopolysaccharides / pharmacology
  • Microglia / cytology
  • Microglia / drug effects
  • Microglia / metabolism
  • Molecular Dynamics Simulation
  • Neuroprotective Agents / chemistry*
  • Neuroprotective Agents / metabolism
  • Neuroprotective Agents / pharmacology
  • Neuroprotective Agents / therapeutic use
  • Nuts / chemistry
  • Nuts / metabolism
  • Plant Extracts / chemistry*
  • Structure-Activity Relationship
  • Tacrine / chemistry
  • Tacrine / metabolism

Substances

  • Cytokines
  • Ligands
  • Lipopolysaccharides
  • Neuroprotective Agents
  • Plant Extracts
  • Tacrine
  • Acetylcholinesterase
  • Butyrylcholinesterase