Computational and spectroscopic investigations on boronic acid based fluorescent carbohydrate sensor in aqueous solution at physiological pH 7.5

Bhavya, N. R.; Mahendra, M.; Doreswamy, B. H.; Shankar, Madan Kumar; Gilandoust, Maryam; El-Khatatneh, Nasseem

doi:10.1016/j.molstruc.2019.05.082

Cited by 21 publications

(21 citation statements)

References 53 publications

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“…The methoxy and boronic acid groups have exhibited syn‐periplanar conformations with respect to the phenyl moiety, as indicated by the torsion angle values of 10.8(4)°for (C4‐C5‐O3‐C7), 2.5(4)° for (C1‐C6‐B1‐O1) and 1.9(4)° for (C5‐C6‐B1‐O2), respectively. The geometrical parameters of the compound are found to be in good agreement with the similar reported compounds . The variations of C−C bonds in phenyl moieties are usually attributed to the substituents that caused a change in the charge distribution on the carbon atom of the benzene ring .…”

Section: Resultssupporting

confidence: 90%

“…We have observed this vibration experimentally as pure mode at 1613 and 1586 cm −1 and as mixed with other modes at 1417 and 1245 cm −1 which are in good agreement with reported as well as computed values (see supporting information Table S8).…”

Section: Resultssupporting

confidence: 77%

“…Y. Erdogdu, et al . assigned this vibration at 1203 and 1197 cm −1 in IR and Raman spectra, while Bhavya et al . observed it as a mixed with other bands at 1267, 987 in FT‐IR and 1262.8, 1161.3, 985 cm −1 in Raman spectra.…”

Section: Resultssupporting

confidence: 72%

“…In the literature, C−B vibration mode in phenylboronic acids are reported at 1089 cm −1 , 1080 and 1110 cm −1 , however, some researchers observed this vibration in fluorophenyl boronic acid derivative at 1344 cm −1[51] and 1334 cm −1 . In current study, we have assigned this vibration mode at 1324 cm −1 and its predicted value at 1374 cm −1 for both FT‐IR and DFT, respectively.…”

Section: Resultssupporting

confidence: 65%

“…They also showed that it is possible to describe the photoinduced energy transfer in these systems from the analysis of frontier molecular orbital energies of the individual donor and acceptor moieties . In continuation with our promising research made on boronic acid based carbohydrate sensor as inspired from the vast background, we have recently reported an arylboronic acid derivative for carbohydrate sensing via spectroscopic studies and TD‐DFT calculations, which showed more selectivity towards D‐fructose more than D‐glucose . In continuation to our previous work, we herein currently report on photophysical properties and carbohydrates binding ability of another important arylboronic acid i. e., (5‐fluoro‐2‐methoxyphenyl) boronic acid (BA8).…”

Section: Introductionmentioning

confidence: 58%

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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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Section: Resultssupporting

confidence: 90%

Section: Resultssupporting

confidence: 77%

Section: Resultssupporting

confidence: 72%

Section: Resultssupporting

confidence: 65%

Section: Introductionmentioning

confidence: 58%

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

et al. 2020

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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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Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2019–2020

Harvey

2023

Mass Spectrometry Reviews

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This review is the tenth update of the original article published in 1999 on the application of matrix‐assisted laser desorption/ionization (MALDI) mass spectrometry to the analysis of carbohydrates and glycoconjugates and brings coverage of the literature to the end of 2020. Also included are papers that describe methods appropriate to analysis by MALDI, such as sample preparation techniques, even though the ionization method is not MALDI. The review is basically divided into three sections: (1) general aspects such as theory of the MALDI process, matrices, derivatization, MALDI imaging, fragmentation, quantification and the use of arrays. (2) Applications to various structural types such as oligo‐ and polysaccharides, glycoproteins, glycolipids, glycosides and biopharmaceuticals, and (3) other areas such as medicine, industrial processes and glycan synthesis where MALDI is extensively used. Much of the material relating to applications is presented in tabular form. The reported work shows increasing use of incorporation of new techniques such as ion mobility and the enormous impact that MALDI imaging is having. MALDI, although invented nearly 40 years ago is still an ideal technique for carbohydrate analysis and advancements in the technique and range of applications show little sign of diminishing.

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Computational and spectroscopic investigations on boronic acid based fluorescent carbohydrate sensor in aqueous solution at physiological pH 7.5

Cited by 21 publications

References 53 publications

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

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

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

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2019–2020

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