A New Hyaluronan Modified with β-Cyclodextrin on Hydroxymethyl Groups Forms a Dynamic Supramolecular Network
Jelica Kovačević,
Zdeňka Prucková,
Tomáš Pospíšil,
Věra Kašpárková,
Michal Rouchal,
Robert Vícha
Affiliations
Jelica Kovačević
Department of Chemistry, Faculty of Technology, Tomas Bata University in Zlín, Vavrečkova 275, 760 01 Zlin, Czech Republic
Zdeňka Prucková
Department of Chemistry, Faculty of Technology, Tomas Bata University in Zlín, Vavrečkova 275, 760 01 Zlin, Czech Republic
Tomáš Pospíšil
Centre of the Region Haná for Biotechnological and Agricultural Research, Department of Chemical Biology and Genetics, Faculty of Science, Palacký University Olomouc, Šlechtitelů 241/27, CZ-783 71 Olomouc, Czech Republic
Věra Kašpárková
Department of Fat, Surfactant and Cosmetics Technology, Faculty of Technology, Tomas Bata University in Zlín, Vavrečkova 275, 760 01 Zlin, Czech Republic
Michal Rouchal
Department of Chemistry, Faculty of Technology, Tomas Bata University in Zlín, Vavrečkova 275, 760 01 Zlin, Czech Republic
Robert Vícha
Department of Chemistry, Faculty of Technology, Tomas Bata University in Zlín, Vavrečkova 275, 760 01 Zlin, Czech Republic
A new hyaluronan derivative modified with β-cyclodextrin units (CD-HA) was prepared via the click reaction between propargylated hyaluronan and monoazido-cyclodextrin (CD) to achieve a degree of substitution of 4%. The modified hyaluronan was characterized by 1H-nuclear magnetic resonance spectroscopy (NMR) and size exclusion chromatography. Subsequent 1H-NMR and isothermal calorimetric titration experiments revealed that the CD units on CD-HA can form virtual 1:1, 1:2, and 1:3 complexes with one-, two-, and three-site adamantane-based guests, respectively. These results imply that the CD-HA chains used the multitopic guests to form a supramolecular cross-linked network. The free CD-HA polymer was readily restored by the addition of a competing macrocycle, which entrapped the cross-linking guests. Thus, we demonstrated that the new CD-HA polymer is a promising component for the construction of chemical stimuli-responsive supramolecular architectures.
