Evaluation of Two Synthetic Glucose Probes for Fluorescence-Lifetime-Based Sensing

We evaluated two anthracene derivatives with covently attached boronic acid groups for fluorescence-lifetime-based sensing of glucose. These anthracene derivatives also contained alkyl amino groups, which quenched the anthracene emission by photo-induced electron transfer. Both anthracene derivatives displayed increased intensities and lifetime in the presence of glucose, as seen from the frequency-domain measurements. A fluorescence lifetime change from 9.8 to 12.4 and 5.7 to 11.8 ns is observed, after the addition of glucose, for the anthracene substituted with one and two boronic acid groups, respectively. This results in a change in the phase angle up to 15° and 30° and in the modulation up to 12 and 25% at 30 MHz for these compounds, respectively. Titration curves in the presence of BSA and micelles are also presented to show the potential interferences from biomolecules. Dissociation constants were evaluated for both compounds, and association with glucose was found to be reversible. Importantly, the apparent glucose binding constants are about 5- to 10-fold smaller with phase, modulation, or mean lifetime than with intensities measurements, shifting the glucose-sensitive range to physiological values. Combining these results and the use of a simple UV-LED as excitation source, the results show an interesting potential of these two compounds in the development of lifetime base devices using synthetic probes for glucose.