Development of Supramolecular Saccharide Sensors Based on Cyclodextrin Complexes and Self-assembling Systems

Abstract

Cyclodextrins (CDs) are water-soluble host compounds having nano-size hydrophobic cavities that enable them to incorporate organic molecules in water. Optically inert CDs can be efficiently combined with various types of chromoionophores and fluoroionophores. In this study, using diverse combinations of phenylboronic acid fluorescent sensors and azoprobes with CDs, the unique saccharide recognition functions of CD, chemically modified CD, and CD gel complexes based on their synergistic function are clarified, thereby confirming their use as supramolecular saccharide sensors. To realize novel supramolecular chirality, the twisted structure of two ditopic azoprobes inside the γ-CD chiral cavity is controlled by multi-point recognition of guest ions in water. As different types of supramolecular saccharide sensors, phenylboronic acidbased self-assembling systems are also reviewed.

Electrochemical Assay for Extremely Selective Recognition of Fructose Based on 4‐Ferrocene‐Phenylboronic Acid Probe and β‐Cyclodextrins Supramolecular Complex

“…[ 58 ] On the other hand, a combination of two or more PBA molecules is necessary to detect glucose. [ 33,59 ] Also in this case, 1 H NMR, C NMR analysis, [ 60 ] and computer modeling [ 61 ] highlights that hydroxyl group at 1,2 and 4,6 position binds to two boronic acids. Thus, the formation of 4‐ferrocene‐phenylboronic acid (4‐Fc‐PB) with natural‐β‐cyclodextrins (β‐CDs) complex prevents two 4‐Fc‐PB probes to be close enough and to bind the two sites of the glucose molecule because of stoichiometric reasons.…”

Phosphate-sensing with (di-(2-picolyl)amino)quinazolines based on a fluorescence on–off system

“…Having determined the binding abilities and the uorescence behaviour of the developed probes, we turned to examine the use of cyclodextrins (CyDs) to improve the selectivity and sensitivity of the ATP sensing, based on a reported multipoint recognition system. 28,29 It was assumed that the introduction of the dpa probe into the hydrophobic cavity of 3-uorophenyl boronic acid (FPB)-modied CyD could likely allow the binding of ATP, wherein, the Cu-dpa recognizes the phosphoric acid unit of ATP, and the FPB recognizes the 1,2-cis-diol unit of the adenosine simultaneously (Fig. 3).…”

Selective Sugar Recognition by Anthracene-Type Boronic Acid Fluorophore/Cyclodextrin Supramolecular Complex Under Physiological pH Condition

“…Over the past several decades, the development of sugar recognition molecules using phenylboronic acid (PBA) has been widely conducted (James et al, 1996; Kanekiyo and Hiraoki, 2005; Anslyn, 2007; Egawa et al, 2007, 2009; Fujita et al, 2008; Minami et al, 2014; Iwami et al, 2015; Tsuchido et al, 2015, 2016, 2017; Zhai et al, 2015; Shimomura et al, 2016; Wu et al, 2016, 2017; Nishiyabu et al, 2018). PBA is known to form cyclic boronate ester with the cis -diol group in the sugar.…”