Arylboronic acids with strong fluorescence intensity changes upon sugar binding

Laughlin, Sarah; Ying-ji, Wang; Ni, Nanting; Wang, Binghe

doi:10.1515/hc-2011-0052

Cited by 8 publications

(3 citation statements)

References 1 publication

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“…Boronic acids are the important building blocks in carbon-carbon bond formation in organic synthesis. In addition to their application in synthetic organic chemistry, they also found application in recognition of nucleic acids, adenosine triphosphate (ATP) and fluoride ions [1,2,3,4,5,6,7,8,9,10,11,12,13]. Though they usually exist in neutral trigonal planar form, can comfortably change into tetrahedral anionic form at pH value being higher the pKa.…”

Section: Introductionmentioning

confidence: 99%

Investigation of interaction between boronic acids and sugar: effect of structural change of sugars on binding affinity using steady state and time resolved fluorescence spectroscopy and molecular docking

Melavanki

Kusanur²,

Sadasivuni

et al. 2020

Heliyon

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Binding interactions of boronic acid derivatives viz. 2-Methylphenylboronic acid (B1) and 3-Methoxyphenylboronic acid (B2) with mono saccharides (arabinose, fructose and galactose) and disaccharides (sucrose, lactose and maltose) in aqueous condition at pH 7.4 by means of fluorescence spectroscopy is reported in the present investigation. Sugar sensing as well as continuous glucose monitoring (CGM) plays a significant role in diabetes regulation. Sugar sensors mediated through enzymes have their own drawbacks, which led to encouragement to search for designing new sensors through alternate approaches. Among many, fluorescence-based sensors are drawing more attention. Boronic acid-based fluorescence sensors have the capacity to bind reversibly with diols, which makes their demand high in applications. Addition of sugar reduces fluorescence intensities. Change in intensities is associated to cleavage of intermolecular hydrogen bonding which leads in reduced stability of boronate ester. Lineweaver-Burk and Benesi-Hildebrand equation is used for analysing data. Mono sugars are estimated to have higher binding constants. Mutarotation leads to structural changes in saccharides which play a key role in binding interactions. Sugars in furanose form are found to be highly favoured for binding. Molecular docking of B1 and B2 with proteins with PDB ID: 2IPL and 2IPM being periplasmic was done with the help of Schrodinger Maestro 11.2 version. GLIDE scores terms are used for expressing binding affinity.

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Section: Introductionmentioning

confidence: 99%

Investigation of interaction between boronic acids and sugar: effect of structural change of sugars on binding affinity using steady state and time resolved fluorescence spectroscopy and molecular docking

Melavanki

Kusanur²,

Sadasivuni

et al. 2020

Heliyon

View full text Add to dashboard Cite

show abstract

“…In addition, problems in accuracy highlight the requirement to improve areas such as their short period of use, invasiveness, or calibration, as well as difficulties associated with sterilization. [ 3,4 ]…”

Section: Introductionmentioning

confidence: 99%

“…The mechanism of the interaction between boronic acid and sugars through intermediates tetrahedral boronate 2 and boronate esters 3 and 4 is shown in Scheme 1. [ 2–4,19–41 ]…”

Section: Introductionmentioning

confidence: 99%

Understanding the binding interaction between phenyl boronic acid P1 and sugars: determination of association and dissociation constants using S–V plots, steady‐state spectroscopic methods and molecular docking

et al. 2020

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Continuous monitoring of glucose and sugar sensing plays a vital role in diabetes control. The drawbacks of the present enzyme‐based sugar sensors have encouraged the investigation into alternate approaches to design new sensors. The popularity of fluorescence sensors is due to their ability to bind reversibly to compounds containing diol. In this study we investigated the binding ability of phenyl boronic acid P1 for monosaccharides and disaccharides (sugars) in aqueous medium at physiological pH 7.4 using steady‐state fluorescence and absorbance. P1 fluorescence was quenched due to formation of esters with sugars. Absorbance and fluorescence measurements led to results that indicated that the sugars studied could be ordered in terms of their affinity to P1, as stated: sucrose > lactose > galactose > xylose > ribose > arabinose. In each case, the slope of modified Stern–Volmer plots was nearly 1, indicating the presence of only a single binding site in boronic acids for sugars. Docking studies were carried out using Schrodinger Maestro v.11.2 software. The binding affinity of phenyl boronic acid P1 with periplasmic protein (PDB ID 2IPM and 2IPL) was estimated using GlideScore.

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Binding Interaction Between Boronic Acid Derivatives with Monosaccharaides: Effect of Structural Change of Monosaccharaides Upon Binding Using S–V Plots

Bhavya¹,

Melavanki

Narayanappa

et al. 2020

Macromolecular Symposia

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Sugar sensing and continuous monitoring of glucose (CGM) play an important and vital role in controlling diabetes. The present enzyme‐based sugar sensors have their own drawbacks. Problems associated with them have encouraged alternate approaches to design new sensors. Among many, fluorescent intensity change based sensors are drawing more attention. Fluorescence sensors based on boronic acid derivatives are more popular because of their ability to reversibly bind diol‐containing compounds. Here, the binding ability of two boronic acid derivatives, namely 2‐methylphenyl boronic acid (B1) and 3‐methoxyphenyl boronic acid (B2) with mono saccharides (sugars), is under investigation. The sugar concentration is kept nearly 1000 times more than that of boronic acid. The interactions of B1 and B2 with three saccharides (d‐sorbitol, dextrose, and fructose) are studied by absorbance and steady‐state fluorescence. Both B1 and B2 fluorescence is quenched by formation of esters with saccharides. The results of absorbance and fluorescence measurements indicate that the studied sugars can be ordered by their affinity to B1 as: d‐sorbitol > xylose > dextrose and for B2 as: dextrose > xylose > d‐sorbitol. In each case, slope of modified S–V plots is nearly one indicating only a single binding site in boronic acids for sugars.

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Arylboronic acids with strong fluorescence intensity changes upon sugar binding

Cited by 8 publications

References 1 publication

Investigation of interaction between boronic acids and sugar: effect of structural change of sugars on binding affinity using steady state and time resolved fluorescence spectroscopy and molecular docking

Investigation of interaction between boronic acids and sugar: effect of structural change of sugars on binding affinity using steady state and time resolved fluorescence spectroscopy and molecular docking

Understanding the binding interaction between phenyl boronic acid P1 and sugars: determination of association and dissociation constants using S–V plots, steady‐state spectroscopic methods and molecular docking

Binding Interaction Between Boronic Acid Derivatives with Monosaccharaides: Effect of Structural Change of Monosaccharaides Upon Binding Using S–V Plots

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