Hypochlorite-Activated Fluorescence Emission and Antibacterial Activities of Imidazole Derivatives for Biological Applications

Abstract

The ability to detect hypochlorite (HOCl/ClO-) in vivo is of great importance to identify and visualize infection. Here, we report the use of imidazoline-2-thione (R1SR2) probes, which act to both sense ClO- and kill bacteria. The N2C=S moieties can recognize ClO- among various typical reactive oxygen species (ROS) and turn into imidazolium moieties (R1IR2) via desulfurization. This was observed through UV-vis absorption and fluorescence emission spectroscopy, with a high fluorescence emission quantum yield (Phi(F) = 43-99%) and large Stokes shift (Delta v similar to 115 nm). Furthermore, the DIM probe, which was prepared by treating the DSM probe with ClO-, also displayed antibacterial efficacy toward not only Escherichia coli (E. coli) and Staphylococcus aureus (S. aureus) but also methicillin-resistant Staphylococcus aureus (MRSA) and extended-spectrum beta-lactamase-producing Escherichia coli (ESBL-EC), that is, antibiotic-resistant bacteria. These results suggest that the DSM probe has great potential to carry out the dual roles of a fluorogenic probe and killer of bacteria.