Phenylboronic acid-modified oligoamine sensitive to monosaccharides and carbon dioxide under physiological conditions
2018
Joseph, Vincent S. | Hong, Jong-Dal
We synthesized and characterized the physicochemical properties of a dual stimuli-responsive receptor designed based on oligoamine incorporating four phenylboronic acid (PBA) groups. This receptor, denoted to OAB, showed excellent responsiveness to major endogenous metabolites, specifically carbon dioxide (CO₂) and monosaccharides glucose and fructose. The reversible complexation of OAB with CO₂ (i.e., association followed by dissociation) was confirmed by changes observed in the conductivity of an OAB solution over time during slow bubbling of CO₂ and then nitrogen (N₂) into the solution. The PBA groups on OAB displayed strong binding to glucose and fructose at the physiological pH 7.4, unlike the majority of the related materials, which require a high pH (>9) for the formation of a boronic ester. The binding constant (Kₑq) values of the synthetic OAB receptor for glucose and fructose were determined to be 5.8 M⁻¹ and 73.4 M⁻¹, respectively. The reversible binding of OAB to green triggers such as CO₂ and monosaccharides at neutral pH makes OAB an ideal choice for designing stimuli-responsive nano- and micro assembles and capsules for drug delivery, and also glycoconjugate receptors for various biomedical applications.
Show more [+] Less [-]AGROVOC Keywords
Bibliographic information
This bibliographic record has been provided by National Agricultural Library