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Materials (Basel). 2015 Mar 20;8(3):1341-1349. doi: 10.3390/ma8031341.

Sugar-Responsive Pseudopolyrotaxane Composed of Phenylboronic Acid-Modified Polyethylene Glycol and γ-Cyclodextrin.

Author information

1
Faculty of Pharmaceutical Sciences, Josai University, Keyakidai, Sakado, Saitama 350-0295, Japan. gyd1203@josai.ac.jp.
2
Faculty of Pharmaceutical Sciences, Josai University, Keyakidai, Sakado, Saitama 350-0295, Japan. yy09237@josai.ac.jp.
3
Faculty of Pharmaceutical Sciences, Josai University, Keyakidai, Sakado, Saitama 350-0295, Japan. yegawa@josai.ac.jp.
4
Faculty of Pharmaceutical Sciences, Josai University, Keyakidai, Sakado, Saitama 350-0295, Japan. rmiki@josai.ac.jp.
5
Faculty of Pharmaceutical Sciences, Josai University, Keyakidai, Sakado, Saitama 350-0295, Japan. kjuni@josai.ac.jp.
6
Faculty of Pharmaceutical Sciences, Josai University, Keyakidai, Sakado, Saitama 350-0295, Japan. sekt1042@josai.ac.jp.

Abstract

We have designed a sugar-responsive pseudopolyrotaxane (PPRX) by combining phenylboronic acid-modified polyethylene glycol (PBA-PEG) and γ-cyclodextrin. Phenylboronic acid (PBA) was used as a sugar-recognition motif in the PPRX because PBA reacts with a diol portion of the sugar molecule and forms a cyclic ester. When D-fructose or D-glucose was added to a suspension of PPRX, PPRX disintegrated, depending on the concentration of the sugars. Interestingly, catechol does not show a response although catechol has a high affinity for PBA. We analyzed the response mechanism of PPRX by considering equilibria.

KEYWORDS:

boronic acid; cyclodextrin; drug delivery; pseudopolyrotaxane; stimuli-responsive material

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