β-phenethylamine--a phenylalanine derivative in brain--contributes to oxidative stress by inhibiting mitochondrial complexes and DT-diaphorase: an in silico study

CNS Neurosci Ther. 2013 Aug;19(8):596-602. doi: 10.1111/cns.12113. Epub 2013 May 3.

Abstract

Aim: Till date, the mode of action of β-PEA on neurons is not well illustrated. We tested the hypothesis that β-PEA has the ability to cause oxidative stress by inhibiting the antioxidant enzyme DT-diaphorase and mitochondrial complexes (Complex-I and complex-III).

Methods: Using molecular docking as a tool, we here studied and compared the inhibitory capacity of β-PEA on DT-diaphorase and mitochondrial complexes. Three-dimensional structures of mitochondrial complexes and DT-diaphorase and their ligands were downloaded from the respective data banks, and free energy of binding (docking scores) were determined.

Results: The present finding demonstrated for the first time that β-PEA potentiates reactive oxygen species generation by inhibiting the antioxidant enzyme DT-diaphorase, in addition to the mitochondrial complex-I and complex-III.

Conclusion: As lowering of cellular antioxidant molecules is evident in many neurodegenerative disorders, β-PEA-induced lowering of DT-diaphorase activity may have the capability to cause neurodegeneration, which may be potentiated by its ability to inhibit mitochondrial complexes. Thus, β-PEA-due to its cumulative actions-may be more potent in causing neurodegeneration as compared to other endogenous neurotoxins.

Keywords: DT-diaphorase; Mitochondrial complex-I; Mitochondrial complex-III; Molecular docking; Neurodegeneration; Oxidative stress; Parkinson's disease.

MeSH terms

  • Animals
  • Binding Sites / physiology
  • Brain Chemistry / drug effects
  • Brain Chemistry / physiology*
  • Cattle
  • Computer Simulation
  • Electron Transport Complex I / antagonists & inhibitors
  • Electron Transport Complex I / metabolism
  • Humans
  • Mitochondria / metabolism*
  • NAD(P)H Dehydrogenase (Quinone) / antagonists & inhibitors*
  • NAD(P)H Dehydrogenase (Quinone) / metabolism
  • Oxidative Stress / physiology*
  • Phenethylamines / chemistry
  • Phenethylamines / pharmacology*
  • Phenylalanine / chemistry
  • Phenylalanine / pharmacology
  • X-Ray Diffraction

Substances

  • Phenethylamines
  • phenethylamine
  • Phenylalanine
  • NAD(P)H Dehydrogenase (Quinone)
  • Electron Transport Complex I