A Long-Wavelength Fluorescent Probe for Saccharides Based on Boronic-Acid Receptor

Authors

  • Hongyan Bai,

    1. Shanghai Key Laboratory of Functional Materials Chemistry, School of Chemistry and Molecular Engineering, East China University of Science and Technology, Shanghai 200237, China
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  • Qian Sun,

    1. Shanghai Key Laboratory of Functional Materials Chemistry, School of Chemistry and Molecular Engineering, East China University of Science and Technology, Shanghai 200237, China
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  • Haiyu Tian,

    1. Shanghai Key Laboratory of Functional Materials Chemistry, School of Chemistry and Molecular Engineering, East China University of Science and Technology, Shanghai 200237, China
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  • Junhong Qian,

    Corresponding author
    1. Shanghai Key Laboratory of Scene Evidence, Center of Material Evidence Identification, Shanghai Public Security Bureau, Shanghai 200083, China
    2. Shanghai Key Laboratory of Functional Materials Chemistry, School of Chemistry and Molecular Engineering, East China University of Science and Technology, Shanghai 200237, China
    • Shanghai Key Laboratory of Scene Evidence, Center of Material Evidence Identification, Shanghai Public Security Bureau, Shanghai 200083, China, Tel.: 0086-021-64253068; Fax: 0086-021-64233068
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  • Lingyi Zhang,

    1. Shanghai Key Laboratory of Functional Materials Chemistry, School of Chemistry and Molecular Engineering, East China University of Science and Technology, Shanghai 200237, China
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  • Weibing Zhang

    Corresponding author
    1. Shanghai Key Laboratory of Scene Evidence, Center of Material Evidence Identification, Shanghai Public Security Bureau, Shanghai 200083, China
    2. Shanghai Key Laboratory of Functional Materials Chemistry, School of Chemistry and Molecular Engineering, East China University of Science and Technology, Shanghai 200237, China
    • Shanghai Key Laboratory of Scene Evidence, Center of Material Evidence Identification, Shanghai Public Security Bureau, Shanghai 200083, China, Tel.: 0086-021-64253068; Fax: 0086-021-64233068
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Abstract

A single boronic acid-based fluorescent probe (compound CSP) for saccharides was designed and synthesized. The probe, with an α,β-unsaturated ketone conjugated into the coumarin fluorophore, was synthesized by 4 steps from the commercial material 4-diethylamino salicylaldehyde. The electron push-pull effect is enhanced with the N,N-diethyl amino as the electron donor and the carbonyl as the electron acceptor. Both the absorption (463 nm) and emission (616 nm) maxima of CSP are in the visible wavelength region with a Stokes shift of about 150 nm, which ensures CSP a potential probe for biological application. Under near physiological conditions, significant fluorescence enhancement of CSP was observed upon the addition of some saccharides, namely, D-sorbitol, D-fructose, D-glucose, D-mannose and D-galactose. The probe showed relatively high sensitivity towards D-fructose and D-sorbitol, and their detection limits were 0.05 mmol/L and 0.1 mmol/L, respectively.

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