Sugar-dependent solubility and fluorescence property of copolymers consisting of phenylboronic acid and 2-hydroxyethyl methacrylate moieties

Katsuhiko Sato, Tatsuya Nakajima, Yu Yasukawa, Jun Ichi Anzai

Research output: Contribution to journalArticlepeer-review

10 Citations (Scopus)

Abstract

Copolymers consisting of N-3-acrylamidophenylboronic acid (APBA) and 2-hydroxyethyl methacrylate moieties (HEMA) were synthesized and their solubility and fluorescence properties were evaluated in the presence of sugar. The APBA-HEMA copolymer composed of 25 mol% of APBA moiety was found to be poorly soluble in water at pH 7.4. However, the water solubility of APBA-HEMA was improved in the presence of fructose in solution. The solubility of APBA-HEMA was influenced by fructose in a concentration-dependent manner, due to the formation of boronate ester of APBA moiety with fructose added. In addition, APBA-HEMA was modified with fluorescein isothiocyanate (FITC) for the fluorometric detection of sugars. The fluorescence intensity of FITC-modified APBA-HEMA was dependent on the type and concentration of sugars in solution. The fluorescence intensity of FITC-modified APBA-HEMA was highly enhanced by the addition of fructose, while the fluorescent response was negligibly small when other sugars were added. Thus, usefulness of FITC-modified APBA-HEMA for the selective determination of fructose was demonstrated.

Original languageEnglish
Pages (from-to)807-814
Number of pages8
JournalPolymer Bulletin
Volume65
Issue number8
DOIs
Publication statusPublished - 2010 Nov 1

Keywords

  • Boronate ester
  • Fluorescence
  • Fructose
  • Optical density
  • Phenylboronic acid

ASJC Scopus subject areas

  • Chemistry(all)
  • Condensed Matter Physics
  • Polymers and Plastics
  • Materials Chemistry

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