Abstract
In association with increasing diabetes prevalence, it is desirable to develop new glucose sensing systems with low cost, ease of use, high stability and good portability. Boronic acid is one of the potential candidates for a future alternative to enzyme-based glucose sensors. Boronic acid derivatives have been widely used for the sugar recognition motif, because boronic acids bind adjacent diols to form cyclic boronate esters. In order to develop colorimetric sugar sensors, boronic acid-conjugated azobenzenes have been synthesized. There are several types of boronic acid azobenzenes, and their characteristics tend to rely on the substitute position of the boronic acid moiety. For example, o-substitution of boronic acid to the azo group gives the advantage of a significant color change upon sugar addition. Nitrogen-15 Nuclear Magnetic Resonance (NMR) studies clearly show a signaling mechanism based on the formation and cleavage of the B–N dative bond between boronic acid and azo moieties in the dye. Some boronic acid-substituted azobenzenes were attached to a polymer or utilized for supramolecular chemistry to produce glucose-selective binding, in which two boronic acid moieties cooperatively bind one glucose molecule. In addition, boronic acid-substituted azobenzenes have been applied not only for glucose monitoring, but also for the sensing of glycated hemoglobin and dopamine.
Highlights
The growing number of people with diabetes is a serious issue worldwide
The combination of boronic acid and azo dye has been successfully used for the development of color sensors for a compound containing adjacent diol structure
We developed a series of o-boronic acid substituted azobenzenes that shows a drastic color change upon sugar addition
Summary
The growing number of people with diabetes is a serious issue worldwide. It has increased from 153 million in 1980 to 347 million in 2008 [1]. For this purpose, urine test strips have been widely used. Urine test strips have been widely used They are easy to use, painless and low cost, and there is no need for electronic devices. The self-monitoring of blood glucose is recommended for diabetes patients who control their blood glucose level with medicines [3,4,5,6]. It is recommended that type 1 diabetes patients, who have defects in insulin production, perform self-blood glucose monitoring at least three times a day [3]. Continuous monitoring systems based on enzymes have been developed and used practically. This review provides a brief overview of the sugar binding ability of boronic acids, and the applications of them in optical sensing systems, and summarizes recent studies for a colorimetric sugar sensing system using boronic acid-substituted azobenzene derivatives
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