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Synthesis and Evaluation of New Benzodioxole- Based Thiosemicarbazone Derivatives as Potential Antitumor Agents

Mehlika Dilek Altıntop1, Halide Edip Temel2, Belgin Sever3

  • 1Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Anadolu University, 26470 Eskişehir, Turkey. mdaltintop@anadolu.edu.tr.

Molecules (Basel, Switzerland)
|November 24, 2016
PubMed

Insights

A novel benzodioxole-based thiosemicarbazone derivative, compound 5, shows potent anticancer effects against lung and glioma cells. Its mechanism involves inducing apoptosis and inhibiting DNA synthesis, independent of cholinesterase activity.

Area of Science:

  • Medicinal Chemistry
  • Cancer Biology
  • Pharmacology

Background:

  • Thiosemicarbazone derivatives are explored for anticancer properties.
  • Benzodioxole scaffolds offer unique structural features for drug design.
  • Understanding the mechanism of action is crucial for developing effective cancer therapies.

Purpose of the Study:

  • Synthesize and evaluate novel benzodioxole-based thiosemicarbazone derivatives for cytotoxic activity.
  • Investigate the correlation between anticancer effects and cholinesterase inhibition.
  • Elucidate the mechanism of action of promising anticancer agents.

Main Methods:

  • Cytotoxicity assays on A549 (lung adenocarcinoma), C6 (glioma), and NIH/3T3 (fibroblast) cell lines.
  • Inhibition assays for acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE).
  • Assessment of DNA synthesis, apoptosis, and mitochondrial membrane potential.
  • SIRT1 inhibitory activity evaluation and molecular docking studies.

Main Results:

  • Compound 5, 4-(1,3-Benzodioxol-5-yl)-1-([1,1'-biphenyl]-4-ylmethylene)thiosemicarbazide, demonstrated significant anticancer activity against C6 and A549 cells with low toxicity to NIH/3T3 cells.
  • Compound 5 induced apoptosis (early and late) and disrupted mitochondrial membrane potential in cancer cells.
  • It exhibited DNA synthesis inhibitory activity and SIRT1 inhibitory potential.
  • No significant inhibition of AChE or BuChE was observed for compound 5, indicating no correlation with cholinesterases.

Conclusions:

  • Compound 5 is a promising anticancer agent with a mechanism involving apoptosis induction and DNA synthesis inhibition.
  • The anticancer activity of compound 5 is independent of its cholinesterase inhibitory effects.
  • Further investigation into SIRT1 inhibition may provide deeper mechanistic insights.
Keywords:
SIRT1apoptosisbenzodioxolecancerdocking studiesmitochondrial membrane potentialthiosemicarbazone

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