Design and green synthesis of binuclear organoselenium compounds for anticancer evaluation against human lung and breast cancer

Abstract

Herein, we report the synthesis of three new binuclear Organoselenium compounds, dicyclopentyl-1H-imidazole-hexyl-2-selenone (MC₁), dibenzyl-1H-imidazole-hexyl-2-selenone (MC₂), and dipentyl-1H-imidazole-hexyl-2-selenone (MC₃), by deprotonation of corresponding imidazolium salts (ML₁–ML₃) via a green synthetic approach. The structure of the newly prepared compounds was characterized through CHN elemental analysis, FTIR, ¹H-NMR, and ¹³C-NMR spectroscopy. Additionally, the in vitro anticancer activity of all the imidazolium salts and selenium adducts was evaluated against A549, MCF-7 cancer cell lines, and EA.hy 926 normal cells by using MTT assays, with 5-fluorouracil as a reference drug. Our findings revealed that all selenium compounds showed a significantly greater anticancer potential than the respective N-heterocyclic carbene salts. Among them, compound MC₂ bearing a benzyl N-substituent was found to be the most effective, with low IC₅₀ = 1.65 ± 0.21 and 2.42 ± 0.61 µM against A549 and MCF-7 cancerous cells, respectively. Furthermore, computational investigation was conducted to theoretically assess the biological potential of newly prepared selenium N-heterocyclic carbene adducts, aiming to discover new anticancer agents.