Chitosan Cross-Linking with Acetaldehyde Acetals
Here we demonstrate the possibility of using acyclic diethylacetal of acetaldehyde (ADA) with low cytotoxicity for the fabrication of hydrogels via Schiff bases formation between chitosan and acetaldehyde generated in situ from acetals in chitosan acetate solution. This approach is more convenient t...
| Main Authors: | , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2022-01-01
|
| Series: | Biomimetics |
| Subjects: | |
| Online Access: | https://www.mdpi.com/2313-7673/7/1/10 |
| _version_ | 1797472685017530368 |
|---|---|
| author | Alexander Pestov Yuliya Privar Arseny Slobodyuk Andrey Boroda Svetlana Bratskaya |
| author_facet | Alexander Pestov Yuliya Privar Arseny Slobodyuk Andrey Boroda Svetlana Bratskaya |
| author_sort | Alexander Pestov |
| collection | DOAJ |
| description | Here we demonstrate the possibility of using acyclic diethylacetal of acetaldehyde (ADA) with low cytotoxicity for the fabrication of hydrogels via Schiff bases formation between chitosan and acetaldehyde generated in situ from acetals in chitosan acetate solution. This approach is more convenient than a direct reaction between chitosan and acetaldehyde due to the better commercial availability and higher boiling point of the acetals. Rheological data confirmed the formation of intermolecular bonds in chitosan solution after the addition of acetaldehyde diethyl acetal at an equimolar NH<sub>2</sub>: acetal ratio. The chemical structure of the reaction products was determined using elemental analysis and <sup>13</sup>C NMR and FT-IR spectroscopy. The formed chitosan-acetylimine underwent further irreversible redox transformations yielding a mechanically stable hydrogel insoluble in a broad pH range. The reported reaction is an example of when an inappropriate selection of acid type for chitosan dissolution prevents hydrogel formation. |
| first_indexed | 2024-03-09T20:04:44Z |
| format | Article |
| id | doaj.art-59b0e13e71fd4551be4f7f7d45ab66db |
| institution | Directory Open Access Journal |
| issn | 2313-7673 |
| language | English |
| last_indexed | 2024-03-09T20:04:44Z |
| publishDate | 2022-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Biomimetics |
| spelling | doaj.art-59b0e13e71fd4551be4f7f7d45ab66db2023-11-24T00:34:15ZengMDPI AGBiomimetics2313-76732022-01-01711010.3390/biomimetics7010010Chitosan Cross-Linking with Acetaldehyde AcetalsAlexander Pestov0Yuliya Privar1Arseny Slobodyuk2Andrey Boroda3Svetlana Bratskaya4I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22, S. Kovalevskoy Str., 620990 Yekaterinburg, RussiaInstitute of Chemistry Far Eastern Branch, Russian Academy of Sciences, 159, Prosp. 100-letiya Vladivostoka, 690022 Vladivostok, RussiaInstitute of Chemistry Far Eastern Branch, Russian Academy of Sciences, 159, Prosp. 100-letiya Vladivostoka, 690022 Vladivostok, RussiaA.V. Zhirmunsky National Scientific Center of Marine Biology, Far Eastern Branch of Russian Academy of Sciences, 17, Palchevskogo Street, 690041 Vladivostok, RussiaInstitute of Chemistry Far Eastern Branch, Russian Academy of Sciences, 159, Prosp. 100-letiya Vladivostoka, 690022 Vladivostok, RussiaHere we demonstrate the possibility of using acyclic diethylacetal of acetaldehyde (ADA) with low cytotoxicity for the fabrication of hydrogels via Schiff bases formation between chitosan and acetaldehyde generated in situ from acetals in chitosan acetate solution. This approach is more convenient than a direct reaction between chitosan and acetaldehyde due to the better commercial availability and higher boiling point of the acetals. Rheological data confirmed the formation of intermolecular bonds in chitosan solution after the addition of acetaldehyde diethyl acetal at an equimolar NH<sub>2</sub>: acetal ratio. The chemical structure of the reaction products was determined using elemental analysis and <sup>13</sup>C NMR and FT-IR spectroscopy. The formed chitosan-acetylimine underwent further irreversible redox transformations yielding a mechanically stable hydrogel insoluble in a broad pH range. The reported reaction is an example of when an inappropriate selection of acid type for chitosan dissolution prevents hydrogel formation.https://www.mdpi.com/2313-7673/7/1/10chitosanacetaldehyde acetalshydrogelrheology |
| spellingShingle | Alexander Pestov Yuliya Privar Arseny Slobodyuk Andrey Boroda Svetlana Bratskaya Chitosan Cross-Linking with Acetaldehyde Acetals Biomimetics chitosan acetaldehyde acetals hydrogel rheology |
| title | Chitosan Cross-Linking with Acetaldehyde Acetals |
| title_full | Chitosan Cross-Linking with Acetaldehyde Acetals |
| title_fullStr | Chitosan Cross-Linking with Acetaldehyde Acetals |
| title_full_unstemmed | Chitosan Cross-Linking with Acetaldehyde Acetals |
| title_short | Chitosan Cross-Linking with Acetaldehyde Acetals |
| title_sort | chitosan cross linking with acetaldehyde acetals |
| topic | chitosan acetaldehyde acetals hydrogel rheology |
| url | https://www.mdpi.com/2313-7673/7/1/10 |
| work_keys_str_mv | AT alexanderpestov chitosancrosslinkingwithacetaldehydeacetals AT yuliyaprivar chitosancrosslinkingwithacetaldehydeacetals AT arsenyslobodyuk chitosancrosslinkingwithacetaldehydeacetals AT andreyboroda chitosancrosslinkingwithacetaldehydeacetals AT svetlanabratskaya chitosancrosslinkingwithacetaldehydeacetals |