Boronic acid sensors with double recognition sites: a review

Herein, boronic acid-based sensors containing two recognition sites were summarized systematically. By two recognition sites working synergistically, the binding affinity and selectivity of sensors improve significantly.

A water-soluble boronic acid sensor for caffeic acid based on double sites recognition

RSC Advances ◽

10.1039/d0ra00980f ◽

2020 ◽

Vol 10 (47) ◽

pp. 28148-28156

Author(s):

Zhancun Bian ◽

Guiqian Fang ◽

Ran Wang ◽

Dongxue Zhan ◽

Qingqiang Yao ◽

...

Keyword(s):

Synergistic Effect ◽

Caffeic Acid ◽

Binding Affinity ◽

Boronic Acid ◽

Water Soluble ◽

Specific Recognition ◽

Herein, the specific recognition of caffeic acid by the double sites boronic acid sensor 5c is reported. The synergistic effect of the two recognition sites greatly improves the binding affinity and selectivity of the sensor.

Binding affinity of sarpogrelate to 5-HT2A receptor ligand recognition sites in rat renal cortical and mesangial cells in culture

General Pharmacology The Vascular System ◽

10.1016/s0306-3623(98)00266-3 ◽

1999 ◽

Vol 33 (1) ◽

pp. 51-57 ◽

Cited By ~ 2

Author(s):

Hiroaki Nishio ◽

Satoru Yoshikawa ◽

Yukiko Morimoto ◽

Zhiqing Chen ◽

Yoshihiro Nakata

Keyword(s):

Binding Affinity ◽

Mesangial Cells ◽

Ligand Recognition ◽

Receptor Ligand ◽

Cells In Culture ◽

Novel detection method for gallic acid: a water soluble boronic acid-based fluorescent sensor with double recognition sites

Bioorganic & Medicinal Chemistry Letters ◽

10.1016/j.bmcl.2021.128483 ◽

2021 ◽

pp. 128483

Author(s):

Dongxue Zhan ◽

Zhancun Bian ◽

Haizhen Li ◽

Ran Wang ◽

Guiqian Fang ◽

...

Keyword(s):

Gallic Acid ◽

Boronic Acid ◽

Detection Method ◽

Fluorescent Sensor ◽

Water Soluble ◽

BAD-Lectins: Boronic Acid-Decorated Lectins with Enhanced Binding Affinity for the Selective Enrichment of Glycoproteins

Analytical Chemistry ◽

10.1021/ac401581u ◽

2013 ◽

Vol 85 (17) ◽

pp. 8268-8276 ◽

Cited By ~ 25

Author(s):

Ying-Wei Lu ◽

Chih-Wei Chien ◽

Po-Chiao Lin ◽

Li-De Huang ◽

Chang-Yang Chen ◽

...

Keyword(s):

Binding Affinity ◽

Boronic Acid ◽

Selective Enrichment

Probe molecule equipped with boronic acid moiety as a reversible cross-linking group improves its binding affinity

Bioorganic & Medicinal Chemistry Letters ◽

10.1016/j.bmcl.2010.05.052 ◽

2010 ◽

Vol 20 (14) ◽

pp. 4152-4155 ◽

Cited By ~ 2

Author(s):

Naoyuki Kotoku ◽

Xiu-Han Guo ◽

Masayoshi Arai ◽

Motomasa Kobayashi

Keyword(s):

Binding Affinity ◽

Boronic Acid ◽

Probe Molecule ◽

Cross Linking ◽

Acid Moiety

Enhanced Enantioselective Recognition with Diastereoisomeric BINOL Based Chiral Fluorescent Boronic Acid Sensors

Journal of Fluorescence ◽

10.1007/s10895-011-0906-3 ◽

2011 ◽

Vol 21 (6) ◽

pp. 2077-2084 ◽

Cited By ~ 12

Author(s):

Qiuting Li ◽

Huimin Guo ◽

Yubo Wu ◽

Xin Zhang ◽

Yifan Liu ◽

...

Keyword(s):

Boronic Acid ◽

Enantioselective Recognition ◽

Isopropylamino and Isobutylamino Groups as Recognition Sites for Carbohydrates: Acyclic Receptors with Enhanced Binding Affinity toward β-Galactosides

The Journal of Organic Chemistry ◽

10.1021/jo100982x ◽

2010 ◽

Vol 75 (19) ◽

pp. 6416-6423 ◽

Cited By ~ 32

Author(s):

Monika Mazik ◽

Claudia Sonnenberg

Keyword(s):

Binding Affinity ◽

Synthesis of three fluorescent boronic acid sensors for tumor marker Sialyl Lewis X in cancer diagnosis

Tetrahedron Letters ◽

10.1016/j.tetlet.2014.05.112 ◽

2014 ◽

Vol 55 (32) ◽

pp. 4437-4441 ◽

Cited By ~ 11

Author(s):

May-Hua Chang ◽

Chia-Ni Chang

Keyword(s):

Tumor Marker ◽

Cancer Diagnosis ◽

Boronic Acid ◽

Sialyl Lewis X ◽

Lewis X ◽

Sialyl Lewis ◽

Effect of the Electron Donor/Acceptor Orientation on the Fluorescence Transduction Efficiency of the d-PET Effect of Carbazole-Based Fluorescent Boronic Acid Sensors

The Journal of Organic Chemistry ◽

10.1021/jo100119y ◽

2010 ◽

Vol 75 (8) ◽

pp. 2578-2588 ◽

Cited By ~ 63

Author(s):

Xin Zhang ◽

Yubo Wu ◽

Shaomin Ji ◽

Huimin Guo ◽

Peng Song ◽

...

Keyword(s):

Electron Donor ◽

Boronic Acid ◽

Transduction Efficiency ◽

Donor Acceptor ◽

Using Quenching Kinetics and Thermodynamics of Amino-Fluorophores as Empirical Tools for Predicting Boronic Acid Sensors Suitable for Use in Physiological Conditions

Australian Journal of Chemistry ◽

10.1071/ch11297 ◽

2011 ◽

Vol 64 (11) ◽

pp. 1438 ◽

Cited By ~ 3

Author(s):

Nicholas McGregor ◽

Christophe Pardin ◽

W. G. Skene

Keyword(s):

Electron Transfer ◽

Fluorescence Quenching ◽

Boronic Acid ◽

Sulfonic Acid ◽

Phenylboronic Acid ◽

Water Soluble ◽

Time Resolved ◽

Diffusion Limited ◽

Phenylboronic Acids ◽

A series of water-soluble 1-amino-naphthalenes and 2-amino-fluorenes are prepared. These serve as model fluorophores for measuring the thermodynamics and kinetics of fluorescence quenching with phenylboronic acids and aliphatic amines. Steady-state and time-resolved fluorescence quenching kinetics are investigated using the Stern–Volmer method. Diffusion limited quenching constants and exergonic thermodynamics of electron transfer are derived for the 5-amino-1-napthol and 2-aminofluorene derivatives with phenylboronic acid and/or an aliphatic imine. No quenching and endergonic thermodynamics or electron transfer are observed for 5-sulfonamide, 5-sulfonic acid, or 5-hydroxy-7-sulfonic acid aminonaphthalene derivatives. Boronic acid sensors synthesized from these aminofluorophores by reductive amination with 2-formylphenylboronic acid undergo fluorescence revival in the presence of saccharides only when the fluorophore demonstrates diffusion limited quenching kinetics and exergonic thermodynamics of electron transfer with the boronic acid or imine quenchers. Thus, these two properties are suitable empirical tools for predicting saccharide-induced fluorescence revival of boronic acid sensors.