α-tocopherol, a slow-binding inhibitor of acetylcholinesterase

Chem Biol Interact. 2021 Oct 1:348:109646. doi: 10.1016/j.cbi.2021.109646. Epub 2021 Sep 8.

Abstract

Acetylcholinesterase (AChE) is reversibly inhibited by α-tocopherol (α-T). Steady state kinetic analysis shows that α-T is a mixed slow-binding inhibitor of type A of human enzyme (Kci = 0.49 μM; Kui = 1.6 μM) with a residence time of 2 min on target. Molecular dynamics (MD) simulations support this mechanism, and indicate that α-T first forms multiple non-specific interactions with AChE surface near the gorge entrance, then binds to the peripheral side with alkylene chain slowly sliding down the gorge, inducing no significant conformational change. α-T slightly modulates the progressive inhibition of AChE by the cyclic organophosphorus, cresyl saligenylphosphate, accelerating the fast pseudo-first order process of phosphorylation. A moderate accelerating effect of α-T on phosphorylation by paraoxon was also observed after pre-incubation of AChE in the presence of α-T. This accelerating effect of α-T on ex vivo paraoxon-induced diaphragm muscle weakness was also observed. The effect of α-T on AChE phosphylation was interpreted in light of molecular modeling results. From all results it is clear that α-T does not protect AChE against phosphylation by organophosphorus.

Keywords: Acetylcholinesterase; Molecular modeling; Organophosphorus; Slow-binding inhibition; α-tocopherol.

MeSH terms

  • Acetylcholinesterase / chemistry
  • Acetylcholinesterase / metabolism*
  • Cholinesterase Inhibitors / metabolism*
  • Cholinesterase Inhibitors / pharmacology*
  • Humans
  • Kinetics
  • Models, Molecular
  • Phosphorylation
  • Protein Conformation
  • alpha-Tocopherol / metabolism*
  • alpha-Tocopherol / pharmacology*

Substances

  • Cholinesterase Inhibitors
  • Acetylcholinesterase
  • alpha-Tocopherol