Helical assembly of azobenzene-conjugated carbohydrate hydrogelators with specific affinity for lectins

Yukiko Ogawa, Chiharu Yoshiyama, Takuya Kitaoka

研究成果: Contribution to journalArticle査読

66 被引用数 (Scopus)


Carbohydrate-mediated interactions are involved in various biological processes via specific molecular assembly and recognition. Such interactions are enhanced by multivalent effects of the sugar moieties, and thus supramolecular sugar-assembly, i.e., spontaneous association of glycoamphiphiles, is a promising approach to tailor glycocluster formation. In this study, novel sugar-decorated nanofibers were successfully prepared by self-assembly of low molecular weight hydrogelators composed of azobenzene and disaccharide lactones. Circular dichroism measurement of the as-prepared hydrogels indicated that the azobenzene amphiphile containing a lactose moiety possessed (R)-chirality, while the maltose-azobenzene conjugate exhibited (S)-chirality, even though the cellobiose-conjugated azobenzene existed in an achiral form. This suggests that the chiral orientation of the chromophoric azobenzene depended on both the glycosidic linkages and the steric arrangement of hydroxyl groups in the conjugated carbohydrates. Lectin-binding and cell adhesion assays revealed that the nonreducing ends of the conjugated sugar moieties were exposed on the surfaces of self-assembled nanofibrous hydrogels, allowing them to be effectively recognized by the corresponding lectins. In addition, photoisomerization of azobenzene under ultraviolet irradiation induced the sol-gel transitions of the hydrogels. These results demonstrate that the reversibly transformed fibrous glycohydrogels show potential for application as carbohydrate-decorated scaffolds for cell culture engineering.

出版ステータス出版済み - 3 6 2012

All Science Journal Classification (ASJC) codes

  • 材料科学(全般)
  • 凝縮系物理学
  • 表面および界面
  • 分光学
  • 電気化学


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