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

Kamal A 1 , Nazari V M 2 , Yaseen M 3 , Iqbal MA 4 , Ahamed MBK 5 , Majid ASA 6 Show all authors , Bhatti HN 7

Affiliations 

  • 1 Department of Chemistry, University of Agriculture, Faisalabad 38040, Pakistan
  • 2 Department of Pharmacology, School of Pharmaceutical Sciences, Universiti Sains Malaysia, Minden, 11800 Pulau Penang, Malaysia
  • 3 Department of Chemistry, University of Education (Lahore), Faisalabad Campus, Faisalabad, Pakistan
  • 4 Department of Chemistry, University of Agriculture, Faisalabad 38040, Pakistan; Organometallic and Coordination Chemistry Laboratory, Department of Chemistry, University of Agriculture, Faisalabad 38040, Pakistan. Electronic address: adnan.iqbal@uaf.edu.pk
  • 5 EMAN Biodiscoveries Sdn. Bhd., A1-4, Lot 5, Persiaran 2/1, Kedah Halal Park, Kawasan Perindustrian Sungai Petani, 08000 Sungai Petani, Kedah, Malaysia
  • 6 Faculty of Medicine, Quest International University Perak, Ipoh, Perak, Malaysia
  • 7 Department of Chemistry, University of Agriculture, Faisalabad 38040, Pakistan. Electronic address: haq_nawaz@uaf.edu.pk
Bioorg Chem, 2019 09;90:103042.
PMID: 31226469 DOI: 10.1016/j.bioorg.2019.103042

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.

* Title and MeSH Headings from MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine.

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