Michael addition reaction of symmetrically halogenated bischalcones with reduced glutathione assessed by RP-HPLC and RP-HPLC-ESI-MS

Abstract

Chalcones and derivatives are promising drugs, demonstrating, among others, antiviral, anticancer, anti-inflammatory, and antioxidant effects. The bioactivity of chalcones and derivatives are associated with their reactivity with cellular thiols, such as the reduced glutathione (GSH), the most important non-protein thiol compound present in mammals. Here, three symmetrically halogenated bischalcones (SHBCs) were synthesized, and their Michael addition reaction with GSH was studied to investigate if the cytotoxic effects of the compounds were correlated with their GSH-reactivity. Formation of two diastereomeric adducts (GS) was observed as a result of the addition of GSH to one of the unsaturated carbon–carbon bonds and other diastereomeric adducts (BS) were formed on addition of another GSH molecule to the second carbon–carbon double bond. However, reactivity of the compounds with GSH did not directly correlate with their in vitro cancer cell toxicity.