Sugar-responsive smart materials based on phenylboronic acid and cyclodextrin

Abstract

This review focuses on sugar-responsive materials based on phenylboronic acid (PBA) as a sugar-sensing motif and cyclodextrins (CyDs) as a basic skeleton of smart materials. PBA modified α-CyD (PBA-α-CyD) forms a supramolecular polymer through intermolecular interactions between PBA part and CyD cavity. Similarly, PBA-β-CyD forms a head-to-head dimer. Meanwhile, combining PBA-γ-CyD and polyethylene glycol (PEG) produces a molecular necklace. Additionally, combining PBA-modified PEG and native α-CyD or γ-CyD results in another type of molecular necklace. These supramolecular structures are obtained as powders, and their solubility increases in the presence of sugar. Besides the powder type, a unique gel is formed through crosslinking polyvinyl alcohol (PVA) with PBA-triazole-γ-CyD (PBA-Tri-γ-CyD). This gel can contain model drug, and it shows sugar-responsive drug release.The sugar response of all of these smart materials can be explained by the concept of equilibrium. The smart materials are constructed with CyD-guest interactions. The CyD-guest equilibrium moves by a reaction between sugar and PBA moiety attached to the smart material. In these smart materials, sugar induces a dissociation in the CyD-guest interaction, and this dissociation results in sugar-induced disintegration of CyD-guest supramolecular structures.

In-Source Microdroplet Derivatization Using Coaxial Contained-Electrospray Mass Spectrometry for Enhanced Sensitivity in Saccharide Analysis

“…This is partly due to the fact that β-cyclodextrin does not contain any cis -diol groups, which is the preferred orientation for the PBA reaction to proceed efficiently. PBA is also known to form an inclusion complex with β-cyclodextrin due to interactions between the phenyl group of the reagent and the hydrophobic inner cavity of cyclodextrin . Thus, although the β-cyclodextrin phenylboronate ester can be generated via in-source derivatization (as evidenced in Figure ), the lack of cis -diol groups and competing complexation limit reaction yield.…”

Enhancement of natural dyeing properties and UV resistance of silk fibers modified by phenylboronic acid/hydroxypropyl‐β‐cyclodextrin functionalized Fe3O4 particle

“…In recent years, phenylboronic acid (PBA) and its derivatives have attained popular attention because they can react with 1, 2‐ and 1, 3‐diol compounds to generate cyclic esters under alkaline conditions 33–35 . Phenylboronic acid functionalized materials have been widely applied for the enrichment of cis dihydroxyl molecules such as sugars and polyphenols 35–37 . But most of the existing studies focused on such fields as sensing, 38,39 drug loading and delivering for tumor therapy, 40,41 recognition and separation of catecholic flavonoids, 42,43 and so forth, there is little research focused on the enhancing adsorption and fixation of natural dyes for textile fiber.…”

Cell Adhesive Character of Phenylboronic Acid-Modified Insulin and Its Potential as Long-Acting Insulin

“…PBA’s ability to form dynamic covalent bonds is expected to be applicable to many fields. In particular, the reaction between PBA and sugars has been widely investigated to develop blood glucose sensors [5,6,7,8,9,10,11,12] and glucose-responsive insulin delivery systems [13,14,15,16] for diabetes patients. However, the bond between PBA derivatives and glucose is not strong.…”