Saccharide Recognition Based on Self-Assembly of Amphiphilic Phenylboronic Acid Azoprobes

Yuji Tsuchido, Ryo Sato, Nana Nodomi, Takeshi Hashimoto, Kazunari Akiyoshi, Takashi Hayashita

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

We designed amphiphilic phenylboronic acid azoprobes (B-Azo-Cn) and evaluated their saccharide recognition function in relation to the micelle formation changes of the self-assembled B-Azo-Cn. First, we evaluated B-Azo-C8 in a 1% methanol-99% water solution under basic conditions. The wavelength of maximum absorption in the ultraviolet-visible (UV-vis) spectra of B-Azo-C8 was shifted, and the solution showed a color change with the addition of saccharides. The morphology of B-Azo-C8 was evaluated using dynamic light scattering (DLS) measurements and transmission electron microscopy (TEM) observations. B-Azo-C8 formed aggregates in the absence of saccharides and in the presence of glucose. In the presence of fructose, micelle-formed B-Azo-C8 was dispersed, indicating that B-Azo-C8 changed its dispersion state by recognizing fructose. The effect of alkyl chain length on the saccharide recognition ability was examined as well. B-Azo-C4 and B-Azo-C12 did not recognize saccharides in a 1% methanol-99% water solution under basic conditions, indicating that an appropriate alkyl chain length was required for recognizing saccharides. The control of the hydrophilic-lipophilic balance (HLB) was a key factor for saccharide recognition.

Original languageEnglish
Pages (from-to)10761-10766
Number of pages6
JournalLangmuir
Volume32
Issue number41
DOIs
Publication statusPublished - 2016 Oct 18
Externally publishedYes

ASJC Scopus subject areas

  • Materials Science(all)
  • Condensed Matter Physics
  • Surfaces and Interfaces
  • Spectroscopy
  • Electrochemistry

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    Tsuchido, Y., Sato, R., Nodomi, N., Hashimoto, T., Akiyoshi, K., & Hayashita, T. (2016). Saccharide Recognition Based on Self-Assembly of Amphiphilic Phenylboronic Acid Azoprobes. Langmuir, 32(41), 10761-10766. https://doi.org/10.1021/acs.langmuir.6b02917