Ortho-azo substituted phenylboronic acids for colorimetric sugar sensors

Egawa, Yuya; Gotoh, Ryota; Niina, Satoshi; Anzai, Jun‐ichi

doi:10.1016/j.bmcl.2007.02.073

Cited by 43 publications

(16 citation statements)

References 27 publications

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“…ortho-Azo substituted phenylboronic acid-based reporters 17–18 (Figure 5) were reported by Egawa and co-workers 260. The UV absorbance of 17 decreased by 70% at 502 nm upon fructose addition in a methanol/water solution (v/v = 1/1) at pH 10.0 and the binding constant was 36 M −1 .…”

Section: Boronic Acid-based Sensorssupporting

confidence: 53%

Carbohydrate recognition by boronolectins, small molecules, and lectins

Jin

Cheng

Reid

et al. 2009

Medicinal Research Reviews

261

214

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Carbohydrates are known to mediate a large number of biological and pathological events. Small and macromolecules capable of carbohydrate recognition have great potentials as research tools, diagnostics, vectors for targeted delivery of therapeutic and imaging agents, and therapeutic agents. However, this potential is far from being realized. One key issue is the difficulty in the development of "binders" capable of specific recognition of carbohydrates of biological relevance. This review discusses systematically the general approaches that are available in developing carbohydrate sensors and "binders/receptors," and their applications. The focus is on discoveries during the last five years.

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Section: Boronic Acid-based Sensorssupporting

confidence: 53%

Carbohydrate recognition by boronolectins, small molecules, and lectins

Jin

Cheng

Reid

et al. 2009

Medicinal Research Reviews

261

214

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“…We introduced a boronic acid group to the o -position of the azo group. Some o -boronic acid substituted azobenzenes were successfully synthesized with diazo-coupling reactions [65,66]. An azo dye, 6 (Figure 5), which has a basic skeleton of a series of o -boronic acid substituted azobenzenes, shows an absorption maximum at 505 nm in aqueous MeOH, which is significantly red-shifted compared to that of 4-aminoazobenzene (365 nm) [67].…”

Section: O-boronic Acid Substituted Azobenzenementioning

confidence: 99%

Colorimetric Sugar Sensing Using Boronic Acid-Substituted Azobenzenes

2014

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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.

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“…However, there has been increasing interest in the development of a new detection method in the recent decade. The phenylboronic acid derivatives as recognition molecules for sugars have become the focus [20]. As is well known, boronic acids bind the 1,2-diol and 1,3-diol of sugars to form boronate esters under aqueous circumstance [21].…”

Section: Introductionmentioning

confidence: 99%