Designed boronate ligands for glucose-selective holographic sensors.
In this study, 2-acrylamidophenylboronate (2-APB) was synthesised and its ability to bind with glucose was investigated both in solution and when integrated into a holographic sensor. Multiple forms of 2-APB, resulting from the neighbouring effect of the amido group with the boronic acid through an intramolecular B--O-coordinated interaction, were shown to exist in solution by using multinuclear NMR spectrometry. It was found that 2-APB predominantly adopts a zwitterionic tetrahedral form at physiological pH values. The complex formation of 2-APB with glucose and lactate was investigated in DMSO; 2-APB favours binding with glucose rather than lactate and generates a five-membered-ring complex. Furthermore, a 2-APB-based holographic sensor displayed a significant response to glucose with little interference from lactate, and with no dependence on pH in the physiological pH range. These features suggest that the new ligand 2-APB is a potential candidate for the development of glucose-selective sensors.
Yang
Xiaoping
X
Institute of Biotechnology, University of Cambridge, Tennis Court Road, Cambridge, CB2 1QT, UK.
Lee
Mei-Ching
MC
Sartain
Felicity
F
Pan
Xiaohan
X
Lowe
Christopher R
CR
D000577:Amides / Q000737:chemistry; D001665:Binding Sites; D015374:Biosensing Techniques / Q000379:methods*; D001897:Boronic Acids / Q000138:chemical synthesis*; D004121:Dimethyl Sulfoxide / Q000737:chemistry; D005947:Glucose / Q000032:analysis* / Q000737:chemistry; D006696:Holography / Q000379:methods*; D006863:Hydrogen-Ion Concentration; D019344:Lactic Acid / Q000737:chemistry; D008024:Ligands; D013058:Mass Spectrometry; D015203:Reproducibility of Results; D012680:Sensitivity and Specificity
D000577:Amides; D001897:Boronic Acids; D008024:Ligands; D019344:Lactic Acid; D005947:Glucose; C010686:benzeneboronic acid; D004121:Dimethyl Sulfoxide