Curcuminoid Chalcones: Synthesis and Biological Activity against the Human Colon Carcinoma (Caco-2) Cell Line

Abstract

aims: The aim of this study was to design and synthesize a series of curcuminoid chalcones containing active moieties characteristic of curcumin and chalcone-type compounds. background: There are many current scientific reports on the synthesis of various derivatives modelled on the structure of known small-molecular bioactive compounds. Curcuminoid chalcones are an innovative class of compounds with significant therapeutic potential against various diseases and perfectly fit into the current trends in the search for new biologically active substances. objective: The objectives of this scientific paper were to synthesize curcuminoid chalcones and confirm their structures using spectral methods. Additionally, the biological activity of the synthesized compounds was evaluated using various assays, and their anticancer properties and toxicity were studied. method: The proposed derivatives were obtained by the Claisen-Schmidt reaction of selected acetophenones and aldehydes under various conditions, both classical methods - in the solutions and solvent-free microwave (MW) or ultrasound (US) variants. Spectral methods were used to confirm curcumin chalcones structures. Resazurin reduction assay, caspase-3 activity assay and RT-qPCR method were performed, followed by the intracellular reactive oxygen species (ROS) level and lactate dehydrogenase (LDH) release level measurements. result: The designed molecules were successfully synthesised and structurally confirmed by NMR, MS and IR spectroscopy. Examination of the anticancer activity of the most interesting curcuminoid chalcones was carried out. conclusion: Obtained results suggest that compound (3a) increases the metabolism and/or proliferation of the human colon carcinoma (CACO-2) cell line, while compounds (3f) and (3b) showed significant toxicity in the CACO-2 cell line. other: The curcuminoid chalcones tested show promising anticancer potential in the studied cell line.