A Sugar-Functionalized Amphiphilic Pillar[5]arene: Synthesis, Self-Assembly in Water, and Application in Bacterial Cell Agglutination

Guocan Yu †, Yingjie Ma †, Chengyou Han †, Yong Yao †, Guping Tang §, Zhengwei Mao ‡, Changyou Gao ‡, and Feihe Huang *†

†Department of Chemistry and ‡Department of Polymer Science and Engineering, MOE Key Laboratory of Macromolecular Synthesis and Functionalization,Zhejiang University, Hangzhou 310027, P. R. China

§ Department of Chemistry, Institute of Chemical Biology and Pharmaceutical Chemistry, Zhejiang University, Hangzhou 310027, P. R. China

J. Am. Chem. Soc., Article ASAP

DOI: 10.1021/ja405237q

Publication Date (Web): June 24, 2013

A novel sugar-functionalized amphiphilic pillar[5]arene containing galactose groups as the hydrophlic part and alkyl chains as the hydrophobic part was designed and synthesized. It self-assembles in water to produce nanotubes as confirmed by TEM, SEM, and fluorescence microscopy. These nanotubes, showing low toxicity to both cancer and normal cells, can be utilized as excellent cell glues to agglutinate E. coli. The existence of galactoses on these nanotubes provides multivalent ligands that have high affinity for carbohydrate receptors onE. coli.