Light-Induced Production of Reactive Oxygen Species by a Novel Water-Soluble Benzophenone Derivative Containing Quaternary Ammonium Groups and Its Assembly on the Protein Fiber Surface.

Abstract

Developing an efficient antimicrobial surface has important significance in the field of advanced biomaterials. A novel water-soluble benzophenone tetracarboxylamine derivative containing two quaternary ammonium groups, 3,3'-[4,4'-carbonyl-diphthalimide-]-bis(N-benzyl-N,N-dimethyl-N-propyl-1-aminium)dichloride (BPTCA-N), as a photoactive antibacterial agent was designed and synthesized. The ability of BPTCA-N to generate reactive oxygen species (ROS) in solution was investigated by light-induced activity. Its antibacterial activity in a dark environment or UV exposure was tested on Staphylococcus aureus and Escherichia coli. The influences of different solvents and the pH values on the ability of BPTCA-N to generate ROS were also discussed. BPTCA-N possessed high photoactivity and efficient ROS generation ability. The generation of hydroxyl radicals could be greatly affected by addition of other solvents and H+ or OH-. For the BPTCA-N solution at a concentration of 0.2 mmol/L, the reduction of S. aureus and E. coli could all reach 99.99%. The BPTCA-N compound was assembled onto wool protein fibers. The modified protein fabrics also showed excellent photoactivity and antibacterial property against S. aureus and E. coli. For the wool fabric modified with 30 g/L of BPTCA-N, the reduction of S. aureus could reach 99.91% and that of E. coli was 91.23%. BPTCA-N had the synergistic antibacterial effect of quaternary ammonium salt and benzophenones. It has potential application in the biomedical field as highly effective antimicrobial agent or antimicrobial biomaterial.