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Small Multitarget Molecules Incorporating the Enone Moiety.

Thalia Liargkova1, Nikolaos Eleftheriadis2, Frank Dekker3

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|January 10, 2019
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Summary

New chalcone derivatives show multi-target biological activities, inhibiting lipoxygenase (LOX), acetylcholinesterase (AChE), and lipid peroxidation. Some compounds also show promise for Alzheimer's disease (AD) treatment by interfering with Aβ aggregation.

Keywords:
Alzheimeracetylcholinesterase inhibitorsbis-chalconesbis-etherschalconeslipoxygenase inhibitorsmultitargetβ-amyloid peptide

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Area of Science:

  • Medicinal Chemistry
  • Drug Discovery
  • Neuroscience

Background:

  • Chalcones are versatile small molecules with diverse biological activities.
  • Multi-target drugs offer advantages over single-target therapies for complex diseases.
  • Existing therapies for multifactorial diseases often show limited clinical efficacy.

Purpose of the Study:

  • To design and synthesize novel chalcone derivatives as multi-target agents.
  • To evaluate synthesized compounds for inhibitory activities against lipoxygenase (LOX), acetylcholinesterase (AChE), and lipid peroxidation.
  • To assess the potential of these compounds in treating neurodegenerative diseases like Alzheimer's disease (AD).

Main Methods:

  • Chemical synthesis of 2-/4-hydroxy-chalcones and bis-etherified bis-chalcone derivatives.
  • In vitro evaluation of inhibitory activities (LOX, AChE, lipid peroxidation) and cytotoxicity.
  • Circular dichroism (CD) studies to assess interference with amyloid-beta (Aβ) aggregation.
  • In silico prediction of Blood-Brain Barrier (BBB) penetration.

Main Results:

  • Chalcone b4 demonstrated significant inhibition of 15-human LOX (IC50 9.5 µM), with notable anti-AChE and anti-lipid peroxidation effects.
  • Bis-etherified chalcones c11 and c12 exhibited combined anti-LOX, anti-AChE, and anti-lipid peroxidation activities.
  • Compounds c2 and c4 interfered with Aβ aggregation, suggesting potential for Alzheimer's disease (AD) treatment.
  • Most synthesized compounds, except c11, were predicted to cross the Blood-Brain Barrier (BBB) for central nervous system (CNS) activity.

Conclusions:

  • The synthesized chalcone derivatives show promising multi-target pharmacological profiles.
  • Specific bis-chalcone structures possess significant anti-LOX, anti-AChE, and anti-lipid peroxidation activities.
  • Chalcone derivatives c2 and c4 offer potential as therapeutic agents for Alzheimer's disease (AD).
  • The presence of a double enone group in chalcones correlates with enhanced biological activities.