Effect of cyclodextrins on saccharide sensing function of a fluorescent phenylboronic acid in water.
An inclusion complex consisting of a fluorescent phenylboronic acid (C1-APB) and beta-cyclodextrin (beta-CD) acts as a supramolecular saccharide sensor whose response mechanism is based on photoinduced electron transfer (PET). This study evaluated four kinds of cyclodextrins (alpha-CD, beta-CD, gamma-CD, and NH(2)-beta-CD) by comparing their pH profiles, and confirmed that beta-CD was the best host for C1-APB because the C1-APB/beta-CD complex exhibited high affinity for saccharides as well as high fluorescent recovery upon saccharide binding. An investigation of the beta-CD concentration effect revealed the formation of a 1:1 inclusion complex of C1-APB with beta-CD. The observed saccharide selectivity of the C1-APB/beta-CD complex is in the following order: D-fructose (4039 +/- 69 M(-1)) > D-ribose (1083 +/- 26 M(-1)) > L-arabinose (474 +/- 11 M(-1)) > D-galactose (318 +/- 3 M(-1)) > maltotoriose (135 +/- 5 M(-1)) > D-glucose (114 +/- 2 M(-1)) > maltose (81 +/- 2 M(-1)). In addition to monomer emission, dimer emission from pyrene dimers was observed in the spectra for the C1-APB/gamma-CD complex, which allowed a ratiometric analysis. This study shows that the combination of a simple fluorescent probe, C1-APB, with various CDs diversifies the response systems for saccharide recognition.
Ozawa
Rimiko
R
Department of Chemistry, Faculty of Science and Technology, Sophia University, Chiyoda, Tokyo, Japan.
Hashimoto
Takeshi
T
Yamauchi
Akiyo
A
Suzuki
Iwao
I
Smith
Bradley D
BD
Hayashita
Takashi
T
D001897:Boronic Acids / Q000737:chemistry*; D002241:Carbohydrates / Q000032:analysis*; D003505:Cyclodextrins / Q000737:chemistry*; D004583:Electrons; D005453:Fluorescence; D005456:Fluorescent Dyes / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D046911:Macromolecular Substances / Q000737:chemistry; D015394:Molecular Structure; D010777:Photochemistry; D012680:Sensitivity and Specificity; D014867:Water / Q000737:chemistry; D047392:beta-Cyclodextrins / Q000737:chemistry
D001897:Boronic Acids; D002241:Carbohydrates; D003505:Cyclodextrins; D005456:Fluorescent Dyes; D046911:Macromolecular Substances; D047392:beta-Cyclodextrins; D014867:Water; C031215:betadex; C010686:benzeneboronic acid