Progress in Boronic Acid-Based Fluorescent Glucose Sensors (original) (raw)
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UV Cured Boronic Acid Based Fluorescence Sensor for the Determination of Glucose
The use of polymers is finding a significant place in development of sensors. Better selectivity and rapid measurements have been achieved by replacing classical sensor materials with functions of polymers. Several receptors have been employed to detect glucose in fluorescence sensors, and these include enzymes such as glucose oxidase, glucose dehydrogenase and hexokinase/glucokinase, bacterial glucose-binding protein, and boronic acid derivatives. Boronic acid has a important role in the design of glucose sensors. The sensing membrane was prepared with p-Vinylphenylboronicacid (VPBA), Hydroxyethylmethacrylate (HEMA) and Poly(ethylene glycol) diacrylate (PEG-DA). The membran is capable of determining glucose between 0.1 ppm and 0.7 ppm. It can be completely regenerated by using distilled water. The sensor performance characteristics such as response time, dynamic working range and sensitivity were reported. The optical sensor was stable, cost effective, easy to prepare, rapid and si...
The effect of boronic acid-positioning in an optical glucose-sensing ensemble
Tetrahedron, 2006
The quenching of the anionic dye 8-hydroxypyrene-1,3,6-trisulfonic acid trisodium salt (pyranine) with three different boronic acid-substituted benzyl viologens was determined, and the fluorescence signal modulation obtained upon addition of glucose to the dye/ quencher system was also studied. The benzyl viologen that contains boronic acids in the ortho-position (o-BBV) was found to display unique behavior, which can be rationalized by a charge neutralization mechanism facilitated by an intramolecular interaction between sp 3 boronate and the quaternary nitrogen of the viologen. Potentiometric titration and 11 B NMR spectroscopy were used to generate pH profiles for the boronic acids, which provide additional evidence for the proposed mechanism. Ó 2006 Elsevier Ltd. All rights reserved. higher pK a lower pK a Scheme 1. Equilibria between boronic acids and generic diols.
Bioorganic & Medicinal Chemistry, 2005
The synthesis, characterization, and spectral properties of strategically designed boronic acid containing fluorescent sensors, o-, m-, p-BMOQBA, for the potential detection of tear glucose concentrations when immobilized in plastic disposable contact lenses is described. The new probes, BMOQBAs, consist of the 6-methoxyquinolinium nucleus as a fluorescent indicator, and the boronic acid moiety as a glucose chelating group. A control compound BMOQ, which has no boronic acid group and therefore does not bind monosaccharides has also been prepared. In this paper, we show that structural design considerations of the new probes have afforded for their compatibility within the lenses, with reduced probe sugar-bound pK a favorable with the mildly acidic lens environment. In addition, the new probes are readily water soluble, have high quantum yields, and can be prepared by a simple one-step synthetic procedure.
2010
The boronic acid group is an important recognition moiety for sensor design. Herein we report a series of isoquinolinylboronic acids that have extraordinarily high affinities for diol-containing compounds at physiological p H. In addition, 5-and 8-isoquinolinylboronic acids also showed fairly high binding affinities with D-glucose (K a = 42 and 46 M −1 , respectively). For the very first time, weak but encouraging binding with cis-cyclohexanediol was found for these boronic acids. Such binding was coupled with significant fluorescence changes. Furthermore, 4-and 6isoquinolinylboronic acids also showed ability to complex methyl-α-D-glucopyranose (K a = 3 and 2 M −1 , respectively).
A new type of boronic acid fluorescent reporter compound for sugar recognition
Tetrahedron Letters, 2005
Fluorescent boronic acids that change fluorescent properties upon carbohydrate binding are very useful for the preparation of fluorescent sensors for sugars. Herein we report 5-quinolineboronic acid (5-QBA) that shows significant fluorescent property changes through a unique pK a-switching mechanism upon binding a diol in aqueous solution.
Tetrahedron Letters, 2005
The boronic acid moiety is a very useful functional group for the preparation of sugar sensors. Along this line, watersoluble boronic acids that change fluorescent properties upon sugar binding are especially useful as reporter units in fluorescent sensors for carbohydrates. Herein, we report the discovery of a new water-soluble boronic acid (1, dibenzofuran-4-boronic acid) that exhibits unique fluorescence changes at three wavelengths upon binding with sugars under near physiological conditions.