Chiral sugar recognition by a diboronic-acid-appended binaphthyl derivative through rigidification effect

Takeuchi, Masayuki; Yoda, Shoya; Imada, Tomoyuki; Shinkai, Seiji

doi:10.1016/s0040-4020(97)00540-1

Cited by 62 publications

(23 citation statements)

References 34 publications

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“…The ketose, D-fructose, appears to be unique in this regard for reasons that are not entirely clear. This same behavior has been observed for many other bis-phenylboronate systems that have been studied using CD spectroscopy (3,16,40,41). The CD spectra of Eu(4) and Eu (10) in the presence of excess D-glucose are shown in Figure 3.…”

Section: Methodssupporting

confidence: 75%

Cyclen-Based Phenylboronate Ligands and Their Eu³⁺ Complexes for Sensing Glucose by MRI

2004

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Novel cyclen-based phenylboronate ligands and their corresponding Eu(3+) complexes have been examined as glucose sensors using chemical exchange saturation transfer (CEST) MR imaging for detection. Two isomeric bis-phenylboronate complexes, Eu(4) and Eu(10), and a mono-phenylboronate complex, Eu(12), had been prepared and characterized by UV and circular dichroism spectroscopy, mass spectrometry, and CEST imaging. Both the free ligands and their Eu(3+) complexes bind to simple sugars, but their selectivity and binding affinities vary with sugar structure. Interestingly, the free ligands, 4 and 10, are selective for fructose over glucose, but this selectivity order switches in the respective Eu(3+) complexes. Of the complexes examined, Eu(4) shows the highest selectivity and binding affinity for glucose (2275 +/- 266 M(-)(1) at pH 10.2 and 339 +/- 29 M(-)(1) at pH 7). Glucose acts as a "capping"moiety in the Eu(4).glucose binary complex and modulates water exchange between a single Eu(3+)-bound water molecule and bulk water, an effect that can be detected by CEST imaging. Thus, Eu(4) represents a new class of metabolite-specific imaging agents that may allow mapping of metabolites by MRI of the bulk water signal.

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Section: Methodssupporting

confidence: 75%

Cyclen-Based Phenylboronate Ligands and Their Eu³⁺ Complexes for Sensing Glucose by MRI

2004

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“…These results suggest that, in presence of micelles, the probes are located in the micelle and cannot interact with the glucose present in solution. For compound 1, the dissociation constant is in the millimolar range, which is characteristic of the boronic acid group (23,25,26,40). For compound 2, this dissociation constant goes down to the submillimolar range.…”

Section: Steady-state Measurementsmentioning

confidence: 99%

“…The use of the boronic acid group for the recognition of saccharide has been widely studied by Shinkai, James, and their collaborators (22)(23)(24)(25)(26). Depending on the structure of the molecule and on the number of boronic acid groups present, dissociation constants from micromolar to tens of millimolar can be obtained and a chiral discrimination has also been observed (27).…”

mentioning

confidence: 99%

Evaluation of Two Synthetic Glucose Probes for Fluorescence-Lifetime-Based Sensing

DiCesare

Lakowicz

2001

Analytical Biochemistry

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We evaluated two anthracene derivatives with covalently attached boronic acid groups for fluorescence-lifetime-based sensing of glucose. These anthracene derivatives also contained alkyl amino groups, which quenched the anthracene emission by photo-induced electron transfer. Both anthracene derivatives displayed increased intensities and lifetime in the presence of glucose, as seen from the frequency-domain measurements. A fluorescence lifetime change from 9.8 to 12.4 and 5.7 to 11.8 ns is observed, after the addition of glucose, for the anthracene substituted with one and two boronic acid groups, respectively. This results in a change in the phase angle up to 15 degrees and 30 degrees and in the modulation up to 12 and 25% at 30 MHz for these compounds, respectively. Titration curves in the presence of BSA and micelles are also presented to show the potential interferences from biomolecules. Dissociation constants were evaluated for both compounds, and association with glucose was found to be reversible. Importantly, the apparent glucose binding constants are about 5- to 10-fold smaller with phase, modulation, or mean lifetime than with intensities measurements, shifting the glucose-sensitive range to physiological values. Combining these results and the use of a simple UV-LED as excitation source, the results show an interesting potential of these two compounds in the development of lifetime base devices using synthetic probes for glucose.

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“…Numerous reports have described the use of conformationally flexible arene-based chromophores for the development of chemosensing systems, targeting a diverse range of analytes such as metal cations, [26–32] anions [33–37] and neutral organic molecules. [34, 38–40]…”

Section: Introductionmentioning

confidence: 99%

Spermine detection via metal-mediated ethynylarene ‘turn-on’ fluorescence signaling

Fletcher

Bruck

2015

Sensors and Actuators B: Chemical

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A dicarboxylated ethynylarene was shown to behave as a fluorescent chemosensor for millimolar concentrations of polyamines when mixed with Cd(II), Pb(II) or Zn(II) ions at micromolar concentrations. A bathochromic shift and intensification of fluorescence emission was observed with increasing amounts of metal ion in the presence of aqueous polyamines buffered at pH = 7.6. Such perturbations manifested as ‘turn-on’ signals from a ratiometric comparison of emission intensities at 390 nm versus 340 nm. Using Pb(II) as the metal mediator, spermine was selectively detected as a 40-fold signal enhancement relative to spermidine, putrescine, cadaverine and several other non-biogenic diamines. Evaluation of additional triamine and tetraamine analytes showed the influence that amine group quantity and spacing had on signal generation. By increasing the ratio of Pb(II) relative to ethynylarene, the detection limit for spermine was successfully lowered to a 25 micromolar level. Noncovalent association between ethynylarene, metal ion and polyamine are believed to promote the observed spectroscopic changes. This study exploits the subtle impact that polyamine structural identity has on transition metal chelation to define a new approach towards polyamine chemosensor development.

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Chiral sugar recognition by a diboronic-acid-appended binaphthyl derivative through rigidification effect

Cited by 62 publications

References 34 publications

Cyclen-Based Phenylboronate Ligands and Their Eu³⁺ Complexes for Sensing Glucose by MRI

Cyclen-Based Phenylboronate Ligands and Their Eu³⁺ Complexes for Sensing Glucose by MRI

Evaluation of Two Synthetic Glucose Probes for Fluorescence-Lifetime-Based Sensing

Spermine detection via metal-mediated ethynylarene ‘turn-on’ fluorescence signaling

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Chiral sugar recognition by a diboronic-acid-appended binaphthyl derivative through rigidification effect

Cited by 62 publications

References 34 publications

Cyclen-Based Phenylboronate Ligands and Their Eu3+ Complexes for Sensing Glucose by MRI

Cyclen-Based Phenylboronate Ligands and Their Eu3+ Complexes for Sensing Glucose by MRI

Evaluation of Two Synthetic Glucose Probes for Fluorescence-Lifetime-Based Sensing

Spermine detection via metal-mediated ethynylarene ‘turn-on’ fluorescence signaling

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Product

Resources

About

Cyclen-Based Phenylboronate Ligands and Their Eu³⁺ Complexes for Sensing Glucose by MRI

Cyclen-Based Phenylboronate Ligands and Their Eu³⁺ Complexes for Sensing Glucose by MRI