Green synthesis of selenium based N-heterocyclic carbene compounds; structural, in-vitro anticancer and molecular docking studies

Hayat K 1 , Tariq U 2 , Wong QA 3 , Quah CK 3 , Majid ASA 4 , Nazari V M 5 Show all authors , Ahamed MBK 6 , Iqbal MA 7 , Tirmizi SA 8

Affiliations 

  • 1 Department of Chemistry, Quaid-I-Azam University, Islamabad 45320, Pakistan; Department of Chemistry, Government P/G College of Science, Faisalabad 38000, Pakistan
  • 2 Department of Chemistry, The Minhaj University, Lahore 54770, Pakistan
  • 3 X-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, Penang 11800, Malaysia
  • 4 Faculty of Medicine, Quest International University Perak, Ipoh, Perak, Malaysia
  • 5 Department of Pharmacology, School of Pharmaceutical Sciences, Universiti Sains Malaysia, Minden 11800, Pulau Penang, Malaysia; School of Pharmacy, University August 17, 1945 14350 Jakarta, Indonesia
  • 6 EMAN Biodiscoveries Sdn. Bhd., A1-4, Lot 5, Persiaran 2/1, Kedah Halal Park, Kawasan Perindustrian Sungai Petani, 08000 Sungai Petani, Kedah, Malaysia
  • 7 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
  • 8 Department of Chemistry, Quaid-I-Azam University, Islamabad 45320, Pakistan. Electronic address: satirmizi_qau@yahoo.com
Comput Biol Chem, 2021 Oct;94:107567.
PMID: 34500323 DOI: 10.1016/j.compbiolchem.2021.107567

Abstract

Benzimidazolium salts (3-6) were synthesized as stable N-Heterocyclic Carbene (NHC) precursors and their selenium-NHC compounds/Selenones (7-10) were prepared using water as a solvent. Characterization of each of the synthesized compounds was carried out by various analytical and spectroscopic (FT-IR, 1H-, 13C NMR) methods. X-ray crystallographic analyses of single crystals obtained for salts 3 and 5 were carried out. Synthesized salts and their Se-NHCs were tested in-vitro for their anticancer potential against Cervical Cancer Cell line from Henrietta Lacks (HeLa), Breast cancer cell line (MDA-MB-231), Adenocarcinoma cell line (A549) and human normal endothelial cell line (EA.hy926). MTT assay was used for analysis and compared with standard drug 5-flourouracil. Benzimidazolium salts (3-6) and their selenium counter parts (7-10) were found potent anticancer agents. Salt 3-5 were found to be potent anticancer against HeLa with IC50 values 0.072, 0.017 and 0.241 μM, respectively, which are less than standard drug (4.9 μM). The Se-NHCs (7-10) had also shown significant anticancer potential against HeLa with IC50 values less than standard drug. Salts 3, 4 against EA.hy926, compounds 3,5,6, and 10 against MDA-MB-321, and compounds 4, 10 against A-549 cell line were found more potent anticancer agents with IC50 values less than standard drug. Molecular docking for (7-10) showed their good anti-angiogenic potential having low binding energy and significant inhibition constant values with VEGFA (vascular endothelial growth factor), EGF (human epidermal growth factor), COX1 (cyclooxygenase-1) and HIF (hypoxia inducible factor).

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

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