Fluorescent sensors based on boronic acids

Christopher R. Cooper; Tony D. James

doi:10.1117/12.347553

3 May 1999 Fluorescent sensors based on boronic acids

Christopher R. Cooper, Tony D. James

Proceedings Volume 3602, Advances in Fluorescence Sensing Technology IV; (1999) https://doi.org/10.1117/12.347553
Event: BiOS '99 International Biomedical Optics Symposium, 1999, San Jose, CA, United States

Abstract

Sensor systems have long been needed for detecting the presence in solution of certain chemically or biologically important species. Sensors are used in a wide range of applications from simple litmus paper that shows a single color change in acidic or basic environments to complex biological assays that use enzymes, antibodies and antigens to display binding events. With this work the use of boronic acids in the design and synthesis of sensors for saccharides (diols) will be presented. The fluorescent sensory systems rely on photoinduced electron transfer (PET) to modulate the observed fluorescence. When saccharides form cyclic boronate esters with boronic acids, the Lewis acidity of the boronic acid is enhanced and therefore the Lewis acid-base interaction between the boronic acid and a neighboring amine is strengthened. The strength of this acid-base interaction modulates the PET from the amine (acting as a quencher) to anthracene (acting as a fluorophore). These compounds show increased fluorescence at neutral pH through suppression of the PET from nitrogen to anthracene on saccharide binding. The general strategy for the development of saccharide selective systems will be discussed. The potential of the boronic acid based systems will be illustrated using the development of glucose and glucosamine selective fluorescent sensors as examples.

Citation Download Citation

Christopher R. Cooper and Tony D. James "Fluorescent sensors based on boronic acids", Proc. SPIE 3602, Advances in Fluorescence Sensing Technology IV, (3 May 1999); https://doi.org/10.1117/12.347553

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