Glucose-responsive vesicular sensor based on boronic acid–glucose recognition in the ARS/PBA/DBBTAB covesicles

Wang, Qiusheng; Li, Guangquan; Xiao, Wenyi; Qi, Haixia; Li, Guowen

doi:10.1016/j.snb.2006.01.030

Cited by 25 publications

(21 citation statements)

References 28 publications

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“…Li and co-workers reported a glucose-responsive vesicular sensor based on boronic acid–glucose recognition in co-vesicles (Scheme 11) 237. The amphiphile, 4-(4-dodecyloxybiphenyl-4-yloxy) butyl trimethylammonium bromide 50 (DBBTAB) is a quaternary ammonium salt, which can form vesicles at low concentrations in aqueous media 237.…”

Section: Boronic Acid-based Sensorsmentioning

confidence: 99%

See 1 more Smart Citation

Carbohydrate recognition by boronolectins, small molecules, and lectins

Jin

Cheng

Reid

et al. 2009

Medicinal Research Reviews

287

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 Sensorsmentioning

confidence: 99%

“…The amphiphile, 4-(4-dodecyloxybiphenyl-4-yloxy) butyl trimethylammonium bromide 50 (DBBTAB) is a quaternary ammonium salt, which can form vesicles at low concentrations in aqueous media 237. DBBTAB vesicles have positively charged surface, which attracts negatively charged alizarin red S (ARS) to form co-vesicles.…”

Section: Boronic Acid-based Sensorsmentioning

confidence: 99%

Carbohydrate recognition by boronolectins, small molecules, and lectins

Jin

Cheng

Reid

et al. 2009

Medicinal Research Reviews

287

214

View full text Add to dashboard Cite

show abstract

“…In addition, it was shown that this assay is rather versatile and can be used to determine binding constants for a range of phenylboronic acids with various carbohydrates . The interaction of carbohydrates with boronic acids immobilized on nanoparticles and liposomes has also been investigated successfully by using ARS as a reporter molecule …”

Section: Introductionmentioning

confidence: 99%

A Self‐Assembled Sensor for Carbohydrates on the Surface of Cyclodextrin Vesicles

Himmelein

Ravoo

2016

Chemistry A European J

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A supramolecular carbohydrate sensor was prepared by self-assembly of unilamellar bilayer vesicles of amphiphilic β-cyclodextrin with a boronic acid-adamantane conjugate (PBA-AD), which binds strongly to β-cyclodextrin through host-guest interactions (K ≈4×10 m ), so the vesicle surface exhibits multiple boronic acid receptors for carbohydrates. The binding of diols to the functionalized vesicles was tested with alizarin red S (ARS) as a reporter dye by using fluorescence and UV/Vis spectroscopy. Analysis of the competitive binding of monosaccharides revealed pH-dependent (pH 7.4-10.1) binding constants in the range of 100-3000 m for d-fructose and 5-400 m for d-glucose. Interestingly, the self-assembled sensor showed fluorescence intensity enhanced by about fivefold and a binding affinity to the reporter dye increased by about eightfold in comparison to PBA-AD and ARS without vesicles. This is attributed to increased local concentration of ARS and PBA-AD on the surface of the vesicles. Detection of d-fructose and d-glucose was possible in the physiologically relevant range in dilute aqueous solution.

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“…The fluorescence of the reporter is different in the bound and unbound states, yielding a change in measured signal as the reporter is displaced from the boronic acid. Wang and coauthors 9 developed glucose sensing vesicles using this mechanism with phenylboronic acid, glucose, and the fluorescent reporter alizarin red S (ARS). 9 Alizarin red S was electrostatically coupled to cationic quaternary ammonium salts that self-assembled into vesicles in solution.…”

Section: Introductionmentioning

confidence: 99%