Green synthesis of selenium based N-heterocyclic carbene compounds; structural,in-vitro anticancer and molecular docking studies |
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Affiliation: | 1. Department of Chemistry, Quaid-I-Azam University, Islamabad 45320, Pakistan;2. Department of Chemistry, Government P/G College of Science, Faisalabad 38000, Pakistan;3. Department of Chemistry, The Minhaj University, Lahore 54770, Pakistan;4. X-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, Penang 11800, Malaysia;5. Department of Chemistry, University of Agriculture, Faisalabad 38040, Pakistan;6. Organometallic and Coordination Chemistry Laboratory, Department of Chemistry, University of Agriculture, Faisalabad 38040, Pakistan;7. Department of Pharmacology, School of Pharmaceutical Sciences, Universiti Sains Malaysia, Minden 11800, Pulau Penang, Malaysia;8. Faculty of Medicine, Quest International University Perak, Ipoh, Perak, Malaysia;9. EMAN Biodiscoveries Sdn. Bhd., A1–4, Lot 5, Persiaran 2/1, Kedah Halal Park, Kawasan Perindustrian Sungai Petani, 08000 Sungai Petani, Kedah, Malaysia;10. School of Pharmacy, University August 17, 1945 14350 Jakarta, Indonesia;1. Department of chemistry, University of Agriculture Faisalabad, Pakistan;2. Gaziantep University, Faculty of Arts and Sciences, Department of Chemistry, 27310, Gaziantep, Turkey;3. Department of Chemistry, Government College University Lahore, Pakistan;4. Department of Chemistry, Pure and Applied Chemistry Group, Faculty of Sciences, University of Sharjah, P.O. Box 27272, Sharjah, United Arab Emirates;5. Department of Biology, college of Science, Taif University, P.O. Box 11099, Taif 21944, Saudi Arabia;6. Department of Biotechnology, college of science, Taif University, P.O. Box 11099, Taif 21944, Saudi Arabia;1. The School of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia;2. Centre for Nano and Material Sciences, Jain University, Jain Global Campus, Bangalore 562 112, Karnataka, India;3. The School of Biological Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia;1. School of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia;2. Department of Pharmacology and Toxicology, Virginia Commonwealth University, Richmond 23298-0613, USA;3. EMAN Research and Testing Laboratory, School of Pharmacy, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia;4. Department of Chemistry, University of Agriculture Faisalabad, 38000 Pakistan;1. Department of Biochemistry, Faculty of Pharmacy, University of Cumhuriyet, 58140 Sivas, Turkey;2. Dept. of Pharmaceutical and Biomedical Sciences, University of Georgia, Athens, GA, Greece;3. Department of Basic Education, Faculty of Education, University of Cumhuriyet, 58140 Sivas, Turkey;4. Department of Chemistry, Faculty of Science and Art, University of İnönü, 44280 Malatya, Turkey;5. Catalysis Research and Application Center, University of İnönü, 44280 Malatya, Turkey;6. Department of Physics, University of Sargodha, Sargodha, Pakistan;7. The Scientific And Technological Research Council of Turkey, 06100 Ankara, Turkey;8. Interdisciplinary Toxicology Program, University of Georgia, Athens, GA, Greece;1. Department of Chemistry, University of Agriculture, Faisalabad, 38000, Pakistan;2. Punjab Bio-energy Institute, University of Agriculture, Faisalabad, 38040, Pakistan;1. Department of Chemistry, University of Agriculture Faisalabad, Faisalabad 38000, Pakistan;2. Gaziantep University, Faculty of Arts and Sciences, Department of Chemistry, +9027310 Gaziantep, Turkey;3. Department of Chemistry, COMSATS University Islamabad, Lahore Campus, Defense road, Lahore, Pakistan;4. Center for Advanced Drug Research, COMSATS University Islamabad, Abbottabad Campus, Abbottabad 22060, Pakistan;5. Chemistry department, Faculty of Sciences, Pure and Applied Chemistry Group, University of Sharjah, P. O.Box 27272, Sharjah, United Arab Emirates;6. National Institute of Oceanography and Fisheries, kayet Bay, Alexandria, Egypt;7. Division of Science and Technology, University of Education Lahore, Lahore, Pakistan;8. Physics Department, Faculty of Science and Arts, King Khalid University, Muhayl Asser, Saudi Arabia;9. Center of Plasma Technology, Al-Azhar University, Cario, Egypt;10. Gaziantep University, Institute of Health Sciences, Department of Bioinformatics and Computational Biology, 9027310, Gaziantep Turkey |
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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). |
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Keywords: | Selenium NHCs Cervical cancer (HeLa) Breast cancer (MDA-MB-231) Adenocarcinoma (A-549) Molecular docking |
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