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Colorimetric Sugar Sensing Using Boronic Acid-Substituted Azobenzenes
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 derivativ...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2014
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5453098/ https://www.ncbi.nlm.nih.gov/pubmed/28788510 http://dx.doi.org/10.3390/ma7021201 |
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author | Egawa, Yuya Miki, Ryotaro Seki, Toshinobu |
author_facet | Egawa, Yuya Miki, Ryotaro Seki, Toshinobu |
author_sort | Egawa, Yuya |
collection | PubMed |
description | 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. |
format | Online Article Text |
id | pubmed-5453098 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2014 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-54530982017-07-28 Colorimetric Sugar Sensing Using Boronic Acid-Substituted Azobenzenes Egawa, Yuya Miki, Ryotaro Seki, Toshinobu Materials (Basel) Review 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. MDPI 2014-02-14 /pmc/articles/PMC5453098/ /pubmed/28788510 http://dx.doi.org/10.3390/ma7021201 Text en © 2014 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/). |
spellingShingle | Review Egawa, Yuya Miki, Ryotaro Seki, Toshinobu Colorimetric Sugar Sensing Using Boronic Acid-Substituted Azobenzenes |
title | Colorimetric Sugar Sensing Using Boronic Acid-Substituted Azobenzenes |
title_full | Colorimetric Sugar Sensing Using Boronic Acid-Substituted Azobenzenes |
title_fullStr | Colorimetric Sugar Sensing Using Boronic Acid-Substituted Azobenzenes |
title_full_unstemmed | Colorimetric Sugar Sensing Using Boronic Acid-Substituted Azobenzenes |
title_short | Colorimetric Sugar Sensing Using Boronic Acid-Substituted Azobenzenes |
title_sort | colorimetric sugar sensing using boronic acid-substituted azobenzenes |
topic | Review |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5453098/ https://www.ncbi.nlm.nih.gov/pubmed/28788510 http://dx.doi.org/10.3390/ma7021201 |
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