Green synthesis of selenium-N-heterocyclic carbene compounds: Evaluation of antimicrobial and anticancer potential

Bioorg Chem. 2019 Sep:90:103042. doi: 10.1016/j.bioorg.2019.103042. Epub 2019 Jun 7.

Abstract

Three benzimidazolium salts (III-V) and respective selenium adducts (VI-VIII) were designed, synthesized and characterized by various analytical techniques (FT-IR and NMR 1H, 13C). Selected salts and respective selenium N-Heterocyclic carbenes (selenium-NHC) adducts were tested in vitro against Cervical Cancer Cell line (Hela), Breast Adenocarcinoma cell line (MCF-7), Retinal Ganglion Cell line (RGC-5) and Mouse Melanoma Cell line (B16F10) using MTT assay and the results were compared with standard drug 5-Fluorouracil. Se-NHC compounds and azolium salts showed significant anticancer potential. Molecular docking studies of compounds (VI, VII and VIII) showed strong binding energies and ligand affinity toward following angiogenic factors: VEGF-A (vascular endothelial growth factor A), EGF (human epidermal growth factor), HIF (Hypoxia-inducible factor) and COX-1 (Cyclooxygenase-1) suggesting that the anticancer activity of adducts (VI, VII and VIII) may be due to their strong anti-angiogenic effect. In addition, compounds III-VIII were screened for their antibacterial and antifungal potential. Adduct VI was found to be potent anti-fungal agent against A. Niger with zone of inhibition (ZI) value 27.01 ± 0.251 mm which is better than standard drug Clotrimazole tested in parallel.

Keywords: Breast cancer (MCF-7); Cervical cancer (Hela); N-Heterocyclic carbenes; NHC; Retinal Ganglion cancer (RGC-5); Se-NHC; Selenium.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / metabolism
  • Anti-Bacterial Agents / pharmacology*
  • Antifungal Agents / chemical synthesis
  • Antifungal Agents / metabolism
  • Antifungal Agents / pharmacology*
  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / metabolism
  • Antineoplastic Agents / pharmacology*
  • Aspergillus niger / drug effects
  • Bacillus subtilis / drug effects
  • Benzimidazoles / chemical synthesis
  • Benzimidazoles / metabolism
  • Benzimidazoles / pharmacology*
  • Cell Line, Tumor
  • Cyclooxygenase 1 / metabolism
  • Drug Screening Assays, Antitumor
  • Epidermal Growth Factor / metabolism
  • Escherichia coli / drug effects
  • Green Chemistry Technology
  • Humans
  • Hypoxia-Inducible Factor 1, alpha Subunit / metabolism
  • Mice
  • Microbial Sensitivity Tests
  • Molecular Docking Simulation
  • Organoselenium Compounds / chemical synthesis
  • Organoselenium Compounds / metabolism
  • Organoselenium Compounds / pharmacology*
  • Protein Binding
  • Sheep, Domestic
  • Staphylococcus aureus / drug effects
  • Vascular Endothelial Growth Factor A / metabolism

Substances

  • Anti-Bacterial Agents
  • Antifungal Agents
  • Antineoplastic Agents
  • Benzimidazoles
  • HIF1A protein, human
  • Hypoxia-Inducible Factor 1, alpha Subunit
  • Organoselenium Compounds
  • VEGFA protein, human
  • Vascular Endothelial Growth Factor A
  • Epidermal Growth Factor
  • Cyclooxygenase 1