A glucose-selective fluorescence sensor based on boronicacid-diol recognition

Karnati, Vishnu Vardhan Reddy; Gao, Xingming; Gao, Shouhai; Yang, Wenqian; Ni, Wei; Sankar, S. S.; Wang, Binghe

doi:10.1016/s0960-894x(02)00767-9

Cited by 140 publications

(55 citation statements)

References 26 publications

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“…Boronic acids are known to initially bind to D-glucose in the pyranose form, which then undergoes changes to the furanoseform. 11, 27-29 If the reverse follows the same pathway then one can understand why the dissociation is slower with D-glucose. With both the k off and k on rates on hand, we calculated the thermodynamic binding constants and the results are included in Table 1.…”

Section: Resultsmentioning

confidence: 99%

“…However, there are reports that it takes hours before equilibrium is reached. 11, 12 There have been some kinetic studies of the binding between boric acid/boronic acids and diol by using NMR, 13-15 stopped-flow 16, 17 and temperature jump 15, 18-20 techniques. However, there has never been a detailed study of exactly how fast the binding process occurs between boronic acids with carbohydrates.…”

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: Introductionmentioning

confidence: 99%

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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“…To endow the sensors with fluorescence and ability to bind with cell-surface glycans, the architecture of anthracene-phenylboronic acid was adopted152324353637. In this structural motif, the anthracene fluorescence is quenched by nitrogen lone pair electrons on an amino group.…”

Section: Resultsmentioning

confidence: 99%

In situ recognition of cell-surface glycans and targeted imaging of cancer cells

Cheng

Chen

et al. 2013

Sci Rep

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Fluorescent sensors capable of recognizing cancer-associated glycans, such as sialyl Lewis X (sLex) tetrasaccharide, have great potential for cancer diagnosis and therapy. Studies on water-soluble and biocompatible sensors for in situ recognition of cancer-associated glycans in live cells and targeted imaging of cancer cells are very limited at present. Here we report boronic acid-functionalized peptide-based fluorescent sensors (BPFSs) for in situ recognition and differentiation of cancer-associated glycans, as well as targeted imaging of cancer cells. By screening BPFSs with different structures, it was demonstrated that BPFS1 with a FRGDF peptide could recognize cell-surface glycan of sLex with high specificity and thereafter fluorescently label and discriminate cancer cells through the cooperation with the specific recognition between RGD and integrins. The newly developed peptide-based sensor will find great potential as a fluorescent probe for cancer diagnosis.

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“…Therefore, the application of the boronic acid moiety for chemosensor/boronolectin design is not restricted to diols on aryl and five-membered rings and linear structures. As a matter of fact, there are several examples of boronic acid binding to diols/hydroxyl groups on six-membered rings [5,58,91,92]. Furthermore, immobilized boronic acids have been used to isolate glycans and glycoproteins [93][94][95][96][97][98][99][100][101][102]; free boronic acids have been used for carbohydrate derivatization for mass spectrometric analysis [93,[103][104][105] with much success; SBLs have been used to recognize cell-surface carbohydrate biomarkers which only contain diols on six-membered rings or linear structures [5], and boronic-acid-modified DNA aptamers have been selected to recognize glycoproteins with the ability to differentiate glycosylation variation [57,106].…”

Section: Boronic-acid-based Chemosensorsmentioning

confidence: 99%