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

6 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

Fingerprint

carbohydrates
Self assembly
self assembly
Fructose
Micelles
Chain length
acids
Methanol
Acids
Water
Dynamic light scattering
Glucose
micelles
Transmission electron microscopy
Color
methyl alcohol
Wavelength
ultraviolet spectra
benzeneboronic acid
visible spectrum

ASJC Scopus subject areas

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

Cite this

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

Saccharide Recognition Based on Self-Assembly of Amphiphilic Phenylboronic Acid Azoprobes. / Tsuchido, Yuji; Sato, Ryo; Nodomi, Nana; Hashimoto, Takeshi; Akiyoshi, Kazunari; Hayashita, Takashi.

In: Langmuir, Vol. 32, No. 41, 18.10.2016, p. 10761-10766.

Research output: Contribution to journalArticle

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, vol. 32, no. 41, pp. 10761-10766. https://doi.org/10.1021/acs.langmuir.6b02917
Tsuchido, Yuji ; Sato, Ryo ; Nodomi, Nana ; Hashimoto, Takeshi ; Akiyoshi, Kazunari ; Hayashita, Takashi. / Saccharide Recognition Based on Self-Assembly of Amphiphilic Phenylboronic Acid Azoprobes. In: Langmuir. 2016 ; Vol. 32, No. 41. pp. 10761-10766.
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