A boronic acid-based fluorescent hydrogel for monosaccharide detection

doi:10.1007/s11705-019-1812-5

Front. Chem. Sci. Eng.

2020, Vol. 14

Issue (1) : 112-116 https://doi.org/10.1007/s11705-019-1812-5

COMMUNICATION

A boronic acid-based fluorescent hydrogel for monosaccharide detection

Suying Xu^1,², Adam C. Sedgwick^2,³, Souad A. Elfeky^2,^4,^5,⁶, Wenbo Chen^2,^4,⁷, Ashley S. Jones², George T. Williams², A. Toby A. Jenkins², Steven D. Bull², John S. Fossey⁴(

), Tony D. James²(

)

¹. Department of Biochemistry, Faculty of Science, Beijing University of Chemical Technology, Beijing 100029, China
². Department of Chemistry, University of Bath, Bath BA2 7AY, UK
³. Department of Chemistry, University of Texas at Austin, TX 78712-1224, USA
⁴. School of Chemistry, University of Birmingham, Birmingham B15 2TT, UK
⁵. National Institute of Laser Enhanced Sciences, Cairo University, Giza 12613, Egypt
⁶. Higher Institute for Optics Technology, Sheraton, Cairo 17361, Egypt
⁷. Shanghai Key Laboratory of Materials Protection and Advanced Materials in Electric Power, Shanghai University of Electric Power, Shanghai 200090, China

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Abstract

A boronic acid-based anthracene fluorescent probe was functionalised with an acrylamide unit to incorporate into a hydrogel system for monosaccharide detection. In solution, the fluorescent probe displayed a strong fluorescence turn-on response upon exposure to fructose, and an expected trend in apparent binding constants, as judged by a fluorescence response where D-fructose>D-galactose>D-mannose>D-glucose. The hydrogel incorporating the boronic acid monomer demonstrated the ability to detect monosaccharides by fluorescence with the same overall trend as the monomer in solution with the addition of D-fructose resulting in a 10-fold enhancement (≤0.25 mol/L).

Corresponding Author(s): John S. Fossey,Tony D. James

Just Accepted Date: 20 March 2019 Online First Date: 16 May 2019 Issue Date: 20 January 2020

Cite this article:

Suying Xu,Adam C. Sedgwick,Souad A. Elfeky, et al. A boronic acid-based fluorescent hydrogel for monosaccharide detection[J]. Front. Chem. Sci. Eng., 2020, 14(1): 112-116.

URL:

https://academic.hep.com.cn/fcse/EN/10.1007/s11705-019-1812-5
https://academic.hep.com.cn/fcse/EN/Y2020/V14/I1/112

Fig.1 Shinkai et al. anthracene-based boronic acid PET fluorescence probe for the detection of fructose

Fig.2 Anthracene-based fluorescent monomer (A-M5) for the development of a hydrogel for the detection of monosacharides

Fig.3 Scheme 1 Synthesis of boronic acid fluorescent probes 3 and AM-5

Fig.4 (a) Fluorescent spectral changes of 3 (0.6 µmol/L) with different concentrations of D-fructose in pH 8.21 aqueous methanolic buffer solution (52.1 wt-% methanol (KCl, 10 mmol/L; KH₂PO₄, 2.73 mmol/L and Na₂HPO₄, 2.78 mmol/L)); (b) Fluorescence intensity changes (F/F₀) at 419 nm versus increasing saccharide concentration. l_ex = 370 nm

Fig.5 Fluorescence intensity ratios of AM-5 (F/F₀) at 409 nm versus monosaccharide concentration in a (1:1) 0.1 mol/L KH₂PO₄/0.1 mol/L NaOH, pH 8.00 buffer solution and λ_ex = 370 nm

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