A dioxaborine-based ratiometric fluorescent probe derived from 2-hydroxy-3-pinanone for H2O2 detection and application in food samples and bioimaging.

Abstract

Hydrogen peroxide (H2O2) plays a crucial role in food processing and environmental remediation. Therefore, it is greatly significant to establish an accurate, rapid and sensitive method for H2O2 detection. Based on the natural product skeleton of 2-hydroxy-3-pinanone, a novel ratiometric fluorescent probe DPBO was rationally designed and synthesized via the intramolecular charge transfer (ICT) mechanism, which exhibited excellent detection performance for H2O2, including good selectivity, strong anti-interference ability and no response to other peroxides. In addition, the probe DPBO also exhibited an excellent linear fluorescence response to H2O2 concentration from 1 to 100 μM, and the detection limit was calculated as low as 0.09 μM. This probe was successfully employed for the quantitative detection of H2O2 in diverse real-world food and beverage samples including red wine, beer, tap water, tea, milk and noodle with high accuracy and high recovery rates ranging from 90.30% to 99.67%. Furthermore, the practical utility of probe DPBO was extended to biological systems, and the visualization detection of H2O2 in living HeLa cells and zebrafish was realized. These results demonstrated that probe DPBO possessed favorable biocompatibility and excellent potential for practical applications in both food safety and bioimaging contexts.