A New Hyaluronan Modified with β-Cyclodextrin on Hydroxymethyl Groups Forms a Dynamic Supramolecular Network
by
Jelica Kovačević 1
, Zdeňka Prucková 1, Tomáš Pospíšil 2, Věra Kašpárková 3, Michal Rouchal 1 and Robert Vícha 1,*
Jelica Kovačević 1, Zdeňka Prucková 1, Tomáš Pospíšil 2, Věra Kašpárková 3, Michal Rouchal 1 and Robert Vícha 1,*
1
Department of Chemistry, Faculty of Technology, Tomas Bata University in Zlín, Vavrečkova 275, 760 01 Zlin, Czech Republic
2
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
3
Department of Fat, Surfactant and Cosmetics Technology, Faculty of Technology, Tomas Bata University in Zlín, Vavrečkova 275, 760 01 Zlin, Czech Republic
*
Author to whom correspondence should be addressed.
Molecules 2019, 24(21), 3849; https://doi.org/10.3390/molecules24213849
Received: 11 September 2019 / Revised: 16 October 2019 / Accepted: 23 October 2019 / Published: 25 October 2019
(This article belongs to the Section Organic Chemistry)
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.
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Keywords:
cyclodextrin; sodium hyaluronan; click reaction; host-guest systems; supramolecular network
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MDPI and ACS Style
Kovačević, J.; Prucková, Z.; Pospíšil, T.; Kašpárková, V.; Rouchal, M.; Vícha, R. A New Hyaluronan Modified with β-Cyclodextrin on Hydroxymethyl Groups Forms a Dynamic Supramolecular Network. Molecules 2019, 24, 3849.
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