Tsuchido Yuji, Sato Ryo, Nodomi Nana, Hashimoto Takeshi, Akiyoshi Kazunari, Hayashita Takashi
Department of Materials and Life Sciences, Faculty of Science and Technology, Sophia University , 7-1 Kioi-cho, Chiyoda-ku, Tokyo 102-8554, Japan.
Department of Polymer Chemistry, Graduate School of Engineering, Kyoto University , Kyotodaigaku-Katsura, Nishikyo-ku, Kyoto 615-8510, Japan.
Langmuir. 2016 Oct 18;32(41):10761-10766. doi: 10.1021/acs.langmuir.6b02917. Epub 2016 Oct 4.
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.
