Molecular Fluorescence Sensor for Saccharides Based on Amino Coumarin

Sandanayake, K. R. A. Samankumara; Imazu, Sachiko; James, Tony D.; Mikami, Masafumi; Shinkai, Seiji

doi:10.1246/cl.1995.139

Cited by 23 publications

(10 citation statements)

References 12 publications

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“…In 1995, the Shinkai group synthesized another boronic acid 19 with a coumarin chromophore as an ICT sensor. 107 However, compound 19 only showed a very small shift in fluorescence intensity and wavelength upon addition of sugars ( Fig. 1).…”

Section: Ict Sensorsmentioning

confidence: 96%

Boronolectins and fluorescent boronolectins: An examination of the detailed chemistry issues important for the design

Yan

Fang

Wang

2005

Medicinal Research Reviews

177

162

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Glycans in the form of glycoproteins or glycolipids play very critical roles in various biological and pathological processes including inflammation, cancer metastasis, immune reactions, embryo development, cell-cell communications and adhesions, blood generation, etc. Proteins (lectins) that can recognize carbohydrates have played very important roles in studying glycobiology. Small molecule mimics of lectins will be very useful in the development of new therapeutics and diagnostics. Along this line, boronic acids have been widely used in the design and synthesis of small organic compounds that mimic the function of lectins. This review examines in detail the factors that are important for the design of boronic acid-based lectin mimics, boronolectins.

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Section: Ict Sensorsmentioning

confidence: 96%

Boronolectins and fluorescent boronolectins: An examination of the detailed chemistry issues important for the design

Yan

Fang

Wang

2005

Medicinal Research Reviews

177

162

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“…20 In seminal work, the Shinkai and James groups have prepared saccharide sensing ICT probes that show promise for use in real world applications. 21,22 …”

Section: Ict-based Ratiometric Fluorescent Probesmentioning

confidence: 99%

“…20 In seminal work, the Shinkai and James groups have prepared saccharide sensing ICT probes that show promise for use in real world applications. 21,22 Disulfide-carbamate based naphthalimide derivatives have been widely exploited as ratiometric fluorescent probes for biological thiol detection. [23][24][25][26][27][28] In the presence of thiols, the disulfide bond is readily cleaved to release 4-aminonaphthalimide.…”

Section: Ict-based Ratiometric Fluorescent Probesmentioning

confidence: 99%

Small molecule-based ratiometric fluorescence probes for cations, anions, and biomolecules

2015

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Quantitative determination of specific analytes is essential for a variety of applications ranging from life sciences to environmental monitoring. Optical sensing allows non-invasive measurements within biological milieus, parallel monitoring of multiple samples, and less invasive imaging. Among the optical sensing methods currently being explored, ratiometric fluorescence sensing has received particular attention as a technique with the potential to provide precise and quantitative analyses. Among its advantages are high sensitivity and inherent reliability, which reflect the self-calibration provided by monitoring two (or more) emissions. A wide variety of ratiometric sensing probes using small fluorescent molecules have been developed for sensing, imaging, and biomedical applications. In this research highlight, we provide an overview of the design principles underlying small fluorescent probes that have been applied to the ratiometric detection of various analytes, including cations, anions, and biomolecules in solution and in biological samples. This highlight is designed to be illustrative, not comprehensive.

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“…The amino coumarine boronic acid 62 prepared by Sandanayake et al 296 is an example of an internal charge transfer (ICT) chromophore. Here both fluorescence intensity and wavelength are affected since the nitrogen is directly connected with the chromophore.…”

Section: Other Fluorescent Saccharide Receptorsmentioning

confidence: 99%

Synthetic receptors

Hartley

James

Ward

2000

J. Chem. Soc., Perkin Trans. 1

263

126

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Molecular Fluorescence Sensor for Saccharides Based on Amino Coumarin

Abstract: The intramolecular neighboring group participation of the amino group of 7-aminocoumarin moiety to phenylboronic acid gave fluorescence intensity and spectral changes upon saccharide binding which could be used in fluorescence mapping of saccharides in biological cells.

Cited by 23 publications

References 12 publications

Boronolectins and fluorescent boronolectins: An examination of the detailed chemistry issues important for the design

Boronolectins and fluorescent boronolectins: An examination of the detailed chemistry issues important for the design

Small molecule-based ratiometric fluorescence probes for cations, anions, and biomolecules

Synthetic receptors

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