Thermodynamic analysis of the interaction between 3-aminophenylboronic acid and monosaccharides for development of biosensor

Torun, Özlem; Dudak, Fahriye Ceyda; Baş, Deniz; Tamer, Uğur; Boyaci, İsmail Hakkı

doi:10.1016/j.snb.2009.05.004

Cited by 29 publications

(21 citation statements)

References 50 publications

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“…From literature, it is known that the binding constants for fructose with arylboronic acids are in the mM range (Springsteen and Wang, 2002;James et al, 2006). To examine the binding behavior of this system by ITC, the expected binding constant has to be considered; and hence, the stoichiometry of the binding has to be set to a constant value (Torun et al, 2009). In literature, different binding structures for fructose to arylboronic acids are assigned by different spectroscopic methods and semiempirical calculations (Norrild and Eggert, 1996;Berube et al, 2008).…”

Section: Experimental Designmentioning

confidence: 99%

Label‐free detection of enhanced saccharide binding at pH 7.4 to nanoparticulate benzoboroxole based receptor units

Schumacher

Katterle

Hettrich

et al. 2011

J of Molecular Recognition

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Nanoparticles modified with either 6-amino-1-hydroxy-2,1-benzoxaborolane (3-aminobenzoboroxole) or 3-aminophenylboronic acid were prepared by nucleophilic substitution of a styrene-co-DVB-co-vinylbenzylchloride latex (25 nm). Isothermal titration calorimetry (ITC) was used as a label-free detection method for the analysis of the binding between monosaccharides and these two differently derivatized nanoparticle systems at pH 7.4. Because ITC reveals, thermodynamical parameters such as the changes in enthalpy ΔH, free energy ΔG, and entropy ΔS, possible explanations for the higher binding constants can be derived in terms of entropy and enthalpy changes. In case of the modified nanoparticles, the free energy of binding is dominated by the entropy term. This shows that interfacial effects, besides the intrinsic affinity, lead to a higher binding constant compared with the free ligand. The highest binding constant was found for fructose binding to the benzoboroxole modified nanoparticles: Its value of 1150 M(-1) is twice as high as for the free benzoboroxole and five times as high as with phenylboronic acid or 3-aminophenylboronic acid. In contrast to the binding of fructose to free boronic acids, which is an enthalpically driven process, the binding of fructose to the modified nanoparticles is dominated by the positive entropy term.

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Section: Experimental Designmentioning

confidence: 99%

Label‐free detection of enhanced saccharide binding at pH 7.4 to nanoparticulate benzoboroxole based receptor units

Schumacher

Katterle

Hettrich

et al. 2011

J of Molecular Recognition

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“…For these reasons, many of the newer glucose sensors under development use the boronic acid moiety rather than GOx as the recognition element for glucose [10–27]. This includes sensors based on optical [11–14,16,18,20–21,27], fluorescence [25–26], surface plasmon [23], and swelling pressure measurements [17,24]. Small molecules containing boronic acid have been known for over a century to strongly yet reversibly bind cis-diols on glucose and other monosaccharides to give cyclic boronic acid esters in aqueous media [28], as shown schematically in Figure 1.…”

Section: Introductionmentioning

confidence: 99%

Thermodynamic analysis of the selectivity enhancement obtained by using smart hydrogels that are zwitterionic when detecting glucose with boronic acid moieties

Horkay

Cho

Tathireddy

et al. 2011

Sensors and Actuators B: Chemical

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Because the boronic acid moiety reversibly binds to sugar molecules and has low cytotoxicity, boronic acid-containing hydrogels are being used in a variety of implantable glucose sensors under development, including sensors based on optical, fluorescence, and swelling pressure measurements. However, some method of glucose selectivity enhancement is often necessary, because isolated boronic acid molecules have a binding constant with glucose that is some forty times smaller than their binding constant with fructose, the second most abundant sugar in the human body. In many cases, glucose selectivity enhancement is obtained by incorporating pendant tertiary amines into the hydrogel network, thereby giving rise to a hydrogel that is zwitterionic at physiological pH. However, the mechanism by which incorporation of tertiary amines confers selectivity enhancement is poorly understood. In order to clarify this mechanism, we use the osmotic deswelling technique to compare the thermodynamic interactions of glucose and fructose with a zwitterionic smart hydrogel containing boronic acid moieties. We also investigate the change in the structure of the hydrogel that occurs when it binds to glucose or to fructose using the technique of small angle neutron scattering.

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“…The increase in the lifetime of the network and in the density of cross‐linking at alkaline pH can be reasonably attributed to the increase of the PBA/diol affinity. Binding constants ( K ) obtained from calorimetric data showed that the affinity between PBA and monosaccharides is pH dependent . In the case of glucose, K passes from ≈270 to ≈60 L mol −1 as the pH is decreased from 9 to 8, to reach ≈3 L mol −1 at pH 6.…”

Section: Resultsmentioning

confidence: 99%

Readily Prepared Dynamic Hydrogels by Combining Phenyl Boronic Acid‐ and Maltose‐Modified Anionic Polysaccharides at Neutral pH

Tarus

Hachet

Messager

et al. 2014

Macromol. Rapid Commun.

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Dynamic covalent hydrogels are facilely prepared from biocompatible polysaccharides in physiological conditions by the formation of phenylboronate ester cross-links. This is based on the simple mixing of carboxylate-containing polysaccharides (i.e., hyaluronic acid or carboxymethylcellulose) modified with phenylboronic acid and maltose moieties according to mild coupling reactions performed in aqueous solution. The formation of dynamic networks based on reversible boronic-ester cross-links is demonstrated by analyzing their rheological behavior. This study shows that these gels can adapt their structure in response to chemical stimuli such as variations in pH or addition of glucose and self-heal.

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Thermodynamic analysis of the interaction between 3-aminophenylboronic acid and monosaccharides for development of biosensor

Cited by 29 publications

References 50 publications

Label‐free detection of enhanced saccharide binding at pH 7.4 to nanoparticulate benzoboroxole based receptor units

Label‐free detection of enhanced saccharide binding at pH 7.4 to nanoparticulate benzoboroxole based receptor units

Thermodynamic analysis of the selectivity enhancement obtained by using smart hydrogels that are zwitterionic when detecting glucose with boronic acid moieties

Readily Prepared Dynamic Hydrogels by Combining Phenyl Boronic Acid‐ and Maltose‐Modified Anionic Polysaccharides at Neutral pH

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