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A New Hyaluronan Modified with β-Cyclodextrin on Hydroxymethyl Groups Forms a Dynamic Supramolecular Network
J. Kovačević, Z. Prucková, T. Pospíšil, V. Kašpárková, M. Rouchal, R. Vícha,
Language English Country Switzerland
Document type Journal Article
Grant support
IGA/FT/2019/007
Univerzita Tomáše Bati ve Zlíně
NLK
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- MeSH
- beta-Cyclodextrins chemical synthesis chemistry MeSH
- Click Chemistry MeSH
- Calorimetry MeSH
- Hyaluronic Acid chemical synthesis chemistry MeSH
- Magnetic Resonance Spectroscopy MeSH
- Molecular Structure * MeSH
- Polymers chemical synthesis chemistry MeSH
- Publication type
- Journal Article MeSH
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.
References provided by Crossref.org
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- $a Kovačević, Jelica $u Department of Chemistry, Faculty of Technology, Tomas Bata University in Zlín, Vavrečkova 275, 760 01 Zlin, Czech Republic.
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- $a A New Hyaluronan Modified with β-Cyclodextrin on Hydroxymethyl Groups Forms a Dynamic Supramolecular Network / $c J. Kovačević, Z. Prucková, T. Pospíšil, V. Kašpárková, M. Rouchal, R. Vícha,
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- $a 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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