A New Hyaluronan Modified with β-Cyclodextrin on Hydroxymethyl Groups Forms a Dynamic Supramolecular Network

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 H-nuclear magnetic resonance spectroscop...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2019-10, Vol.24 (21), p.3849
Main Authors: Kovačević, Jelica, Prucková, Zdeňka, Pospíšil, Tomáš, Kašpárková, Věra, Rouchal, Michal, Vícha, Robert
Format: Article
Language:English
Subjects:
Addition polymerization
beta-Cyclodextrins - chemical synthesis
beta-Cyclodextrins - chemistry
Binding sites
Biopolymers
Calorimetry
Chemical reactions
Chemical stimuli
Click Chemistry
click reaction
Crosslinking
cyclodextrin
Cyclodextrins
host-guest systems
Hyaluronic acid
Hyaluronic Acid - chemical synthesis
Hyaluronic Acid - chemistry
Magnetic Resonance Spectroscopy
Molecular Structure
NMR
NMR spectroscopy
Nuclear magnetic resonance
Polymers
Polymers - chemical synthesis
Polymers - chemistry
Size exclusion chromatography
sodium hyaluronan
Substitution reactions
supramolecular network
Titration
β-Cyclodextrin
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Summary: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 H-nuclear magnetic resonance spectroscopy (NMR) and size exclusion chromatography. Subsequent H-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.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules24213849