A New Class of Fluorescent Boronic Acids That Have Extraordinarily High Affinities for Diols in Aqueous Solution at Physiological pH

Cheng, Yunfeng; Ni, Nanting; Yang, Wenqian; Wang, Binghe

doi:10.1002/chem.201000637

Cited by 33 publications

(26 citation statements)

References 39 publications

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“…This observed trend in k on is the same as the thermodynamic binding constants as described previously. 4 The various factors that affect the binding affinity between a boronic acid and a diol have been discussed elsewhere. 7, 8 …”

Section: Resultsmentioning

confidence: 99%

“…Firstly, it is interesting that 4-IQBA showed fluorescent intensity decreased upon binding with D-glucose in the stopped-flow instrument, while we observed fluorescent intensity increased in the binding study using the fluorometer as reported before. 4 One possible reason is again associated with the structural change of the complex. It is possible that the species observed in the stopped-flow experiments was in the pyranose form, while the thermodynamic experiments observed the furanose form.…”

Section: Resultsmentioning

confidence: 99%

“…We have recently described a series of isoquinolinylboronic acids, which show large fluorescent signal changes upon binding. 4 The boronic acids chosen for this study include 4-, 5-, and 8-isoquinolinylboronic acids (4-IQBA, 5-IQBA and 8-IQBA). Their abilities to change fluorescence upon binding allowed for the direct detection of the binding event by using a fluorometer coupled with a stopped-flow instrument.…”

Section: Introductionmentioning

confidence: 99%

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Probing the general time scale question of boronic acid binding with sugars in aqueous solution at physiological pH

Laughlin

Ying-ji

et al. 2012

Bioorganic & Medicinal Chemistry

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The boronic acid group is widely used in chemosensor design due to its ability to reversibly bind diol-containing compounds. The thermodynamic properties of the boronic acid-diol binding process have been investigated extensively. However, there are few studies of the kinetic properties of such binding processes. In this report, stopped-flow method was used for the first time to study the kinetic properties of the binding between three model arylboronic acids, 4-, 5-, and 8-isoquinolinylboronic acids, and various sugars. With all the boronic acid-diol pair sexamined, reactions were complete within seconds. The kon values with various sugars follow the order of D-fructose >D-tagatose>D-mannose >D-glucose. This trend tracks the thermodynamic binding affinities for these sugars and demonstrates that the “on” rate is the key factor determining the binding constant.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Probing the general time scale question of boronic acid binding with sugars in aqueous solution at physiological pH

Laughlin

Ying-ji

et al. 2012

Bioorganic & Medicinal Chemistry

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“…Similar reports were identified with regard to 3‐amino phenylboronic acid compound and has shown interactions with mono and disaccharides and suggested fluorescence quenching by forming esters with sugars showing relatively more predominance for fructose . Likewise, isoquinolinylboronic acids were proven to show good binding properties with glucose and had binding affinity in the range 42–46 M −1 . Naphthalene based fluorescent boronic acid showed 41‐fold enhancement of fluorescence intensity upon binding fructose at pH 7.4 .…”

Section: Introductionmentioning

confidence: 99%

Structural, Quantum Chemical and Spectroscopic Investigations on Photophysical Properties of Fluorescent Saccharide Sensor: Theoretical and Experimental Studies

et al. 2020

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Structure, Hirshfeld surface, spectra and photophysical properties of boronic acid‐based carbohydrate sensor (5‐fluoro‐2‐methoxyphenyl) boronic acid (BA8) has been reported by experimental methods (XRD/FT‐IR/UV/steady state fluorescence) and theoretically by Density functional theory (DFT) model with most accurate functionals (B3LYP/CAM−B3LYP/ M06‐2X). The comparison of theoretical and experimental data exhibited good agreement. Natural bond orbital (NBO) and frontier molecular orbitals (FMOs) have been analysed. The sensing ability of the compound with carbohydrates (D‐glucose and D‐fructose) were studied by UV/fluorescence spectra. The variation of absorbance and fluorescence on pH was rationale with the estimated acid‐base dissociation constants (pKa). Quantum yield (Φ) and fluorescence lifetimes (τ) for the compound and its esters with sugars were calculated. The results of absorbance, fluorescence measurements and calculated photophysical properties indicated fairly selectivity of BA8 with fructose more than the glucose, which is ascertained from both experimental and theoretical results.

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“…Efforts to understand how those factors affect the thermodynamics of the dynamic bond have focused on maximizing the binding affinity (Keq) at physiological pH. 9,42,[44][45][46][47][48][49] In particular, those studies have introduced new classes of boronic acids with high binding affinities, such as Wulff-type boronic acid and benzoxaborole. 9,44,50 In contrast, studies investigating the kinetics of this dynamic reaction are largely motivated by boronic acid-based receptors and sensors, and thus rely on specific model diols to elucidate the speciation and pathways of the complex mechanism (see Electronic Supplementary Information (ESI), Table S1).…”

Section: Introductionmentioning

confidence: 99%

Internal and external catalysis in boronic ester networks

Kang¹,

Kalow²

2021

Preprint

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In dynamic materials, the reversible condensation between boronic acids and diols provides adaptability, self-healing ability, and responsiveness to small molecules and pH. Recent work has shown that the thermodynamics and kinetics of bond exchange determine the mechanical properties of dynamic polymer networks. However, prior studies have focused on how structural and environmental factors influence boronic acid–diol binding affinity, and design rules for tuning the kinetics of this dynamic bond are lacking. In this work, we investigate the effects of diol (or polyol) structure and salt additives on the rate of bond exchange, binding affinity, and the mechanical properties of the corresponding polymer networks. To better mimic the environment of polymer networks in our small-molecule model systems, we incorporated proximal amide groups, which are used to conjugate diols to polymers, and included salts commonly found in buffers. Using one-dimensional selective exchange spectroscopy (1D EXSY), we find that both proximal amides and buffering anions induce significant rate acceleration consistent with internal and external catalysis, respectively. This rate acceleration is reflected in the stress relaxation of gels formed using PEG modified with different alcohols, and in the presence of salts containing acetate or phosphate. These findings contribute to the fundamental understanding of the boronic ester dynamic bond and offer new molecular strategies to tune the macromolecular properties of dynamic materials.

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A New Class of Fluorescent Boronic Acids That Have Extraordinarily High Affinities for Diols in Aqueous Solution at Physiological pH

Cited by 33 publications

References 39 publications

Probing the general time scale question of boronic acid binding with sugars in aqueous solution at physiological pH

Probing the general time scale question of boronic acid binding with sugars in aqueous solution at physiological pH

Structural, Quantum Chemical and Spectroscopic Investigations on Photophysical Properties of Fluorescent Saccharide Sensor: Theoretical and Experimental Studies

Internal and external catalysis in boronic ester networks

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