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Progress in Chemistry 2024, Vol. 36 Issue (1): 106-119 DOI: 10.7536/PC230519 Previous Articles   Next Articles

• Review •

Saccharide Sensors Based on Phenylboronic Acid Derivatives

Tan Shi, Donghui Kou, Yanan Xue, Shufen Zhang, Wei Ma()   

  1. State Key Laboratory of Fine Chemicals, Frontier Science Center for Smart Materials, Dalian University of Technology, Dalian 116024, China
  • Received: Revised: Online: Published:
  • Contact: * e-mail: weima@dlut.edu.cn
  • Supported by:
    National Natural Science Foundation of China(22278064); National Natural Science Foundation of China(21878040); National Natural Science Foundation of China(22238002); Fundamental Research Funds for the Central Universities(DUT22LAB610); Research and Innovation Team Project of Dalian University of Technology(DUT2022TB10)
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Phenylboronic acid, a kind of synthetic molecule that can covalently bind with saccharide, has attracted wide attention in the field of saccharide detection. It has the characteristics of good stability, strong recognition ability and easy coupling with various detection systems. In this paper, the mechanism of phenylboronic acid binding to saccharide and its specific applications in detection was first introduced. What’s more, the strategies for structural modification, in the manner of introducing electron-withdrawing group or electron-donating group into ortho, meta and para position of the boric acid group on the benzene ring, were mainly discussed, and the progress made in reducing pKa and improving the selectivity according to these strategies were summarized. At the same time, the saccharide sensors based on these new phenylboronic acid derivatives in recent years were also summarized, including electrochemical sensors, fluorescence sensors, gels/microgels and photonic crystals, and their detection principles were discussed. The main analytes are monosaccharides with similar structures, such as glucose and fructose. Finally, the research of these sensors based on phenylboronic acid derivatives was compared, and their advantages and disadvantages were analyzed. Meanwhile, the applications of saccharide sensors based on phenylboronic acid derivatives in the future are prospected from two aspects including the integration of diagnosis and treatment and the identification of saccharide in complex chemical environment.

Contents

1 Introduction

2 Phenylboronic acid and its derivatives

2.1 Reaction principle of phenylboronic acid and saccharides

2.2 Structural modification strategy of phenylboronic acid

2.3 Detection principle of saccharides in phenylboronic acid

3 Saccharide sensors based on phenylboronic acid derivatives

3.1 Electrochemical sensors for saccharide detections

3.2 Fluorescent sensors for saccharide detections

3.3 Photonic crystals for saccharide detections

3.4 Gels for saccharide detections

4 Conclusion and outlook

Key words: phenylboronic acid, saccharide, electrochemistry, fluorescence, gel, photonic crystal
Fig. 1 Equilibrium of different forms of phenylboronic acid in solution environment and their response equilibria with saccharides
Fig. 2 (a) Molecular structure of common electron- withdrawing modified phenylboronic acid derivatives；(b) molecular structure of ortho-electron-donating modified boronic acid derivatives; (c) molecular structure of 2-acrylamidophenylboronic acid; (d) molecular structure of common dibasic phenylboronic acid derivatives
Fig. 3 Ionization equilibria of electron-donating group functionalized phenylboronic acid in solution[39]
Fig. 4 Ionization equilibrium of 2-acrylamidophenylboronic acid in solution
Fig. 5 Molecular structure of diboronic acid (DBA2+)[48]
Fig. 6 (a) Mechanism of fructose detection by 4-Ferrocene- phenylboronicacid (4-Fc-PBA)/natural β-cyclodextrins (β-CDs) calibration lines based on (b) oxidation peaks and on (c) reduction peaks (fructose concentration up to 5 mM)[62]
Fig. 7 Plot of shift in the surface potential (ΔVout) at different concentrations of glucose dissolved in human serum (Approximate curve was fitted by Langmuir adsorption isotherm) [64]
Fig. 8 Fluorescence response of composite probe (5?mg·mL?1) upon addition of various concentrations of glucose in a pH 8 PBS solution. Inset: semilogarithmic plot of (F?F0)/F0 of composite probe vs the concentration of glucose [73]
Fig. 9 (a) Structures and synthetic procedure of fluorescence probe 1 and 2[82]; (b) structures of fluorescence probe 1F, 2N and 3Ph[83]
Fig. 10 Fluorescence intensities at 494 nm of 1F/γ-CyD (a) and 2N/γ-CyD (b) at various concentrations of saccharides (D-glucose, D-fructose, D-galactose, and L-glucose) in DMSO/water (2/98 in v/v) (The excitation wavelengths were set as 328 nm for 1F/γ-CyD and 374 nm for 2N/γ-CyD)[83]
Fig. 11 (a) SEM images and (b) glucose response behavior of microgels (5.0 mM PBS, 25.0 ℃)[88]
Fig. 12 Reusability of the hydrogel fibers in sensing glucose(pH=7.4, 1.0~12.0 mM, 24 ℃)[87]
Fig. 13 Stimuli-responsiveness of hydrogels against glucose (0.1 M), fructose (0.1 M), and H2O2 (3%)[93]
Fig. 14 Glucose-dependent <Dh>[Glu]/<Dh>0.0 mM of microgels as a function of the solution temperature, all measurements were made in PBS of pH = 7.4[94]
Fig. 15 Digital photos of P（MMA-NIPAM-AAPBA） three-dimensional photonic crystal sensor based on opal structure at (a) 0 mM and (b) 20 mM glucose concentration[101]
Fig. 16 Reflectance spectrum and photos of inverse opal sensor prepared by adding (a) 0.26 mol (b) 0.52 mol of AAPBA with the increase of glucose concentration[103]
Fig. 17 Peak shift of the Bragg stacks as a function of time in 100 mM glucose solution. Insets show colorimetric readouts of the Bragg stacks, and the control experiment without 3-APBA. Scale bar: 2.0 mm [106]
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