Design, synthesis, and biological evaluation of scutellarein carbamate derivatives as potential multifunctional agents for the treatment of Alzheimer's disease

Chem Biol Drug Des. 2015 Nov;86(5):1168-77. doi: 10.1111/cbdd.12580. Epub 2015 May 20.

Abstract

A series of scutellarein carbamate derivatives were designed and synthesized based on the multitarget-directed drug design strategy for treatment of Alzheimer's disease. Their acetylcholinesterase and butyrylcholinesterase inhibitory activities, antioxidant activities, metals chelation, and neuroprotective effects against hydrogen peroxide-induced PC12 cell injury were evaluated in vitro. The preliminary results indicated that compound 7b exhibited good inhibitory potency toward AChE and BuChE with IC50 values of 1.2 ± 0.03 μm and 22.1 ± 0.15 μm, respectively, possessed the strong antioxidant potency (10.3 trolox equivalents), as well as acted as a selective metal chelator and neuroprotective agent. Furthermore, 7b could improve memory impairment induced by scopolamine, ethanol, and sodium nitrite using the step-down passive avoidance task in vivo and could remarkably decrease the activity of acetylcholinesterase in mice brain. This study indicated that 7b could be considered as a potential multitarget agent against AD.

Keywords: AChE inhibitors; Alzheimer's disease; antioxidant; metal chelator; neuroprotective effects; scutellarein carbamates; synthesis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetylcholinesterase / metabolism
  • Alzheimer Disease / drug therapy*
  • Alzheimer Disease / metabolism
  • Animals
  • Antioxidants / chemistry
  • Antioxidants / pharmacology*
  • Apigenin / chemistry
  • Apigenin / pharmacology*
  • Brain / drug effects
  • Brain / metabolism
  • Butyrylcholinesterase / metabolism
  • Carbamates / chemistry
  • Carbamates / pharmacology*
  • Chelating Agents / chemistry
  • Chelating Agents / pharmacology*
  • Cholinesterase Inhibitors / chemistry
  • Cholinesterase Inhibitors / pharmacology*
  • Drug Design
  • Female
  • Humans
  • Male
  • Memory / drug effects
  • Mice
  • Molecular Targeted Therapy
  • Neuroprotective Agents / chemistry
  • Neuroprotective Agents / pharmacology*
  • PC12 Cells
  • Rats

Substances

  • Antioxidants
  • Carbamates
  • Chelating Agents
  • Cholinesterase Inhibitors
  • Neuroprotective Agents
  • Apigenin
  • Acetylcholinesterase
  • Butyrylcholinesterase
  • scutellarein