Azolium mediated N-Heterocyclic carbene selenium adducts: Synthesis, cytotoxicity and molecular docking studies

Ionic liquids (ILs) are remarkable for biological activities in numerous medical fields. With the aim of enhancing biological potential of azolium based ILs, four new selenium-N-Heterocyclic Carbene (Se-NHC) adducts were synthesized from bis-imidazolium and bis-benzimidazolium molten salts. Synthesized ILs (L-1-L-4) and Se-NHC adducts (C-1-C-4) were confirmed through elemental analysis, chromatographic and spectroscopic techniques including UHPLC-PDA, FTIR, H-1 NMR & C-13 NMR spectroscopy as well as mass spectrometry. The compounds were found stable in solution form for upto 96 h measured spectroscopically and showed partition coefficient with optimum lipophilicity measured through shake flask method. The simulation studies of these compounds for cancerous proteins indicated that there could be good to high anticancer potential due to their high affinity and less binding energies for COX-1, EGF, VEGF-A and HIF cancer protein targets. The In Vitro cytotoxicity study of compounds confirmed that these compounds were found highly active showeing IC50 against HCT-116 (1.074-1.116 mu g mL(-1)), A549 (0.977-1.325 mu g mL(-1)) and MCF-7 (0.869-1.378 mu g mL(-1)) which is almost better than standard drug 5-Flourouracil but slightly lower than cisplatin and oxaliplatin. The interaction study of compounds with albumin proteins (BSA) and hemolysis assay assured their least toxicity. (C) 2021 Elsevier B.V. All rights reserved.