Synthesis of bis‐Naphthol based Organoselenium Antioxidants as Efficient Inhibitors against Biofilms

Abstract

In the present study, synthesis of bis‐naphthol based organoselenium compounds has been described. The synthetic strategy involves electrophilic aromatic addition of alkyl/aryl selenium species at the electron rich center of 2,7‐dihydroxynaphthalene. The reaction with electrophilic selenylating reagents in situ generated by potassium persulphate and diselenides produced desired selenides. Synthesized compounds were studied for their glutathione peroxidase (GPx)‐like antioxidant activities using thiophenol assay. It was observed that all compounds exhibited greater GPx‐like antioxidant activity than diphenyl diselenide used as reference. Further, these GPx mimics were introduced for their antibacterial properties against biofilm formation by Bacillus subtilis and Pseudomonas aeruginosa. To support experimental details, molecular docking studies were also performed to elucidate in silico interactions between the active sites of proteins TsaA and LasR found in Bacillus subtilis and Pseudomonas aeruginosa, respectively. The minimum inhibitory concentration assay was performed for all the antioxidants against Bacillus subtilis and Pseudomonas aeruginosa. Additionally, hemolytic assay has also been carried out to check the impact on red blood cells. Cytotoxicity assessments of antioxidants have also been carried using MTT assay.