Effect of Cyclodextrins on Saccharide Sensing Function of a Fluorescent Phenylboronic Acid in Water

• OZAWA Rimiko

  Department of Chemistry, Faculty of Science and Technology, Sophia University

• HASHIMOTO Takeshi

  Department of Chemistry, Faculty of Science and Technology, Sophia University

• YAMAUCHI Akiyo

  Graduate School of Pharmaceutical Science, Tohoku University

• SUZUKI Iwao

  Graduate School of Pharmaceutical Science, Tohoku University

• SMITH Bradley D.

  Department of Chemistry and Biochemistry, University of Notre Dame

• HAYASHITA Takashi

  Department of Chemistry, Faculty of Science and Technology, Sophia University

Bibliographic Information

Other Title

• Effect of cyclodextrins and saccharide sensing function of a fluorescent phenylboronic acid in water

Abstract

An inclusion complex consisting of a fluorescent phenylboronic acid (C1-APB) and β-cyclodextrin (β-CD) acts as a supramolecular saccharide sensor whose response mechanism is based on photoinduced electron transfer (PET). This study evaluated four kinds of cyclodextrins (α-CD, β-CD, γ-CD, and NH₂-β-CD) by comparing their pH profiles, and confirmed that β-CD was the best host for C1-APB because the C1-APB/β-CD complex exhibited high affinity for saccharides as well as high fluorescent recovery upon saccharide binding. An investigation of the β-CD concentration effect revealed the formation of a 1:1 inclusion complex of C1-APB with β-CD. The observed saccharide selectivity of the C1-APB/β-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/γ-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.

Journal

• Analytical Sciences

  Analytical Sciences 24 (2), 207-212, 2008

  The Japan Society for Analytical Chemistry

Keywords

• Analytical Chemistry

Details

• CRID: 1390001204258439936
• NII Article ID: 130004441602
• NII Article ID: 10021098320
• NII Book ID: AA10500785
• DOI: 10.2116/analsci.24.207
• COI: 1:CAS:528:DC%2BD1cXit1Ogu74%3D
• ISSN: 13482246
• ISSN: 09106340
• NDL BIB ID: 9362792
• PubMed: 18270410
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I9362792
• Web Site: https://link.springer.com/content/pdf/10.2116/analsci.24.207.pdf
• Web Site: https://link.springer.com/article/10.2116/analsci.24.207/fulltext.html
• Web Site: http://www.jstage.jst.go.jp/article/analsci/24/2/24_2_207/_pdf
• Text Lang: en
• Data Source:
  • JaLC
  • NDL
  • Crossref
  • PubMed
  • CiNii Articles
  • KAKEN
• Abstract License Flag: Disallowed