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 <sup>1</sup>H-nucle...
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MDPI AG
2019-10-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/24/21/3849 |
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| author | Jelica Kovačević Zdeňka Prucková Tomáš Pospíšil Věra Kašpárková Michal Rouchal Robert Vícha |
| author_facet | Jelica Kovačević Zdeňka Prucková Tomáš Pospíšil Věra Kašpárková Michal Rouchal Robert Vícha |
| author_sort | Jelica Kovačević |
| collection | DOAJ |
| description | 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 <sup>1</sup>H-nuclear magnetic resonance spectroscopy (NMR) and size exclusion chromatography. Subsequent <sup>1</sup>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. |
| first_indexed | 2024-12-10T17:59:54Z |
| format | Article |
| id | doaj.art-08af353e532342dcb35d3aad9c7c69c0 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-10T17:59:54Z |
| publishDate | 2019-10-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-08af353e532342dcb35d3aad9c7c69c02022-12-22T01:38:48ZengMDPI AGMolecules1420-30492019-10-012421384910.3390/molecules24213849molecules24213849A New Hyaluronan Modified with β-Cyclodextrin on Hydroxymethyl Groups Forms a Dynamic Supramolecular NetworkJelica Kovačević0Zdeňka Prucková1Tomáš Pospíšil2Věra Kašpárková3Michal Rouchal4Robert Vícha5Department of Chemistry, Faculty of Technology, Tomas Bata University in Zlín, Vavrečkova 275, 760 01 Zlin, Czech RepublicDepartment of Chemistry, Faculty of Technology, Tomas Bata University in Zlín, Vavrečkova 275, 760 01 Zlin, Czech RepublicCentre 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 RepublicDepartment of Fat, Surfactant and Cosmetics Technology, Faculty of Technology, Tomas Bata University in Zlín, Vavrečkova 275, 760 01 Zlin, Czech RepublicDepartment of Chemistry, Faculty of Technology, Tomas Bata University in Zlín, Vavrečkova 275, 760 01 Zlin, Czech RepublicDepartment of Chemistry, Faculty of Technology, Tomas Bata University in Zlín, Vavrečkova 275, 760 01 Zlin, Czech RepublicA 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 <sup>1</sup>H-nuclear magnetic resonance spectroscopy (NMR) and size exclusion chromatography. Subsequent <sup>1</sup>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.https://www.mdpi.com/1420-3049/24/21/3849cyclodextrinsodium hyaluronanclick reactionhost-guest systemssupramolecular network |
| spellingShingle | Jelica Kovačević Zdeňka Prucková Tomáš Pospíšil Věra Kašpárková Michal Rouchal Robert Vícha A New Hyaluronan Modified with β-Cyclodextrin on Hydroxymethyl Groups Forms a Dynamic Supramolecular Network Molecules cyclodextrin sodium hyaluronan click reaction host-guest systems supramolecular network |
| title | A New Hyaluronan Modified with β-Cyclodextrin on Hydroxymethyl Groups Forms a Dynamic Supramolecular Network |
| title_full | A New Hyaluronan Modified with β-Cyclodextrin on Hydroxymethyl Groups Forms a Dynamic Supramolecular Network |
| title_fullStr | A New Hyaluronan Modified with β-Cyclodextrin on Hydroxymethyl Groups Forms a Dynamic Supramolecular Network |
| title_full_unstemmed | A New Hyaluronan Modified with β-Cyclodextrin on Hydroxymethyl Groups Forms a Dynamic Supramolecular Network |
| title_short | A New Hyaluronan Modified with β-Cyclodextrin on Hydroxymethyl Groups Forms a Dynamic Supramolecular Network |
| title_sort | new hyaluronan modified with β cyclodextrin on hydroxymethyl groups forms a dynamic supramolecular network |
| topic | cyclodextrin sodium hyaluronan click reaction host-guest systems supramolecular network |
| url | https://www.mdpi.com/1420-3049/24/21/3849 |
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