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

• Published in: Chemical & pharmaceutical bulletin Vol. 65; no. 4; pp. 318 - 325
• Main Authors: Tsuchido, Yuji, Fujiwara, Shoji, Hashimoto, Takeshi, Hayashita, Takashi
• Format: Journal Article
• Language: English
• Published: Japan The Pharmaceutical Society of Japan 2017; Japan Science and Technology Agency
• Subjects: Azo Compounds - chemistry; Boronic Acids - chemistry; Carbohydrates; Carbohydrates - analysis; Chirality; Cyclodextrin; cyclodextrin (CD); Cyclodextrins; Cyclodextrins - chemistry; Fluorescence; Fluorescent Dyes - chemical synthesis; Fluorescent Dyes - chemistry; Holes; Hydrophobic and Hydrophilic Interactions; Hydrophobicity; Macromolecular Substances - chemical synthesis; Macromolecular Substances - chemistry; Organic chemistry; Particle Size; phenylboronic acid; Recognition; Reviews; saccharide recognition; self-assembling system; Self-assembly; Sensors; supramolecular chirality; supramolecular sensor; Surface Properties
• ISSN: 0009-2363; 1347-5223
• DOI: 10.1248/cpb.c16-00963

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 acid-based self-assembling systems are also reviewed.