Dye Displacement Assay for Saccharides using Benzoxaborole Hydrogels

Abstract

Dye displacement assays are a simple but effective method to determine the concentration of target analytes. Previously, we have shown that phenylboronic acid pinacol ester hydrogels (borogels) can be used to develop a boronic acid–Alizarin red S dye displacement assay for the determination of fructose (orange to red). In this work, benzoxaborole hydrogels (BOBgels) were developed, and these BOBgels demonstrated an enhanced apparent binding affinity towards monosaccharides, in particular towards glucose.

A boronic acid-based fluorescent hydrogel for monosaccharide detection

“…The modification of hydrogels to contain boronic-acid binding motifs enables the physical properties of the hydrogel to be reversibly modulated through exposure to saccharide-containing stimuli, i.e., glucose responsivity [20][21][22][23]. Co-authors of this report have developed stimuli responsive hydrogels and fluorescent sensors [24][25][26][27][28][29][30], and as a result, we were motivated to translate a Shinkai-like anthracene-containing boronic acid sensor unit into a hydrogel sensor by linking to an acrylamide functionality, thus generating a fluorescence-on sensor hydrogel for monosaccharide detection.…”

Advances in applied supramolecular technologies

“…8, was only characterized in the 1980s. 59 Over the last two decades, other members of the CB family have been synthesized and purified, including CB [5], CB [7], CB[8], and CB [10] containing 5, 7, 8, or 10 glycoluril subunits, respectively. 60,61 CBs display unique physical, chemical and biological properties, primarily owing to their intrinsic ability to undergo complexation with diverse chemical species resulting in the formation of dynamic hostguest complexes.…”

“…Crystal structure analysis reveals this colour change is due to alteration of the p-p stacking interactions between the benzoquinone and the 1,4-diethoxybenzene units of the pillar[4]-arene [1]quinone scaffold. 105 Additionally, the fluorescence emission properties of an anthracene appended pillar [5]-arene (21) NAC were also found to alter upon exposure to vapours of short chain alkyl ketones such as 2-butanone, 2-pentanone, and 2-hexanone ( Fig. 17).…”

“…[2][3][4] Today, supramolecular chemistry broadly encompasses the study of all types of intermolecular non-covalent bond formation in designed molecular systems, and also incorporates dynamic covalent chemistry. [5][6][7] The body of work undertaken in this field since the late 1960s has twice resulted in the award of the Nobel prize in Chemistry, first in 1987 and again in 2016, for the development of host-guest binding molecules 8 and molecular machines respectively. 9…”

Boronate ester cross-linked PVA hydrogels for the capture and H2O2-mediated release of active fluorophores

“…Boronic acid and boronate esters have found widespread application in material-based applications, in part because of their propensity to bind reversibly with 1,2-and 1,3-diols. [9][10][11][12][13][14][15][16][17][18][19] Such chemistry has been demonstrated inter alia using commercially available PVA and diboronic acid crosslinkers to afford functional PVA-boronate hydrogels. [20][21][22][23][24][25] Boronic acids and boronate esters are well-known to undergo H 2 O 2 -mediated oxidative transformations to afford their corresponding phenol functionalites.…”