α,β-Unsaturated aldehyde of hyaluronan—Synthesis, analysis and applications
| Autor: | Vladimír Velebný, Radovan Buffa, Petra Šedová, Tomáš Bobula, Martina Moravcová, Ivana Basarabová, Lucie Wolfova |
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| Rok vydání: | 2015 |
| Předmět: |
chemistry.chemical_classification
Aldehydes Polymers and Plastics Double bond Chemistry Organic Chemistry Imine Biocompatible Materials Hydrogels Alkenes Hydrogen-Ion Concentration Aldehyde Hydrolysis chemistry.chemical_compound Drug Delivery Systems Ultraviolet visible spectroscopy Drug delivery Self-healing hydrogels Materials Chemistry Organic chemistry Amine gas treating Imines Hyaluronic Acid |
| Zdroj: | Carbohydrate Polymers. 134:293-299 |
| ISSN: | 0144-8617 |
| DOI: | 10.1016/j.carbpol.2015.07.084 |
| Popis: | Hyaluronic acid (HA) modified with an aldehyde group (HA-CHO or HA-aldehyde) has been extensively used for various biomedical applications. The main advantage of the aldehyde moieties is the ability to react with a wide range of amino compounds under physiological conditions. Reactions of aldehydes with primary amines in water are reversible and equilibrium is thoroughly shifted towards starting aldehyde and amine. This work presents an unique modification of HA: α,β-unsaturated aldehyde of HA (4,5-anhydro-6(GlcNAc)-oxo HA or ΔHA-CHO), which allows the primary amines to be attached to HA more effectively in comparison to the saturated HA-CHO. Higher hydrolytic stability is caused by the conjugation of imine with an adjacent --C=C-- double bond. Two strategies for the preparation of unsaturated HA-aldehyde were developed and chemical structures were studied in details. Cross-linked materials prepared from this precursor are biocompatible and suitable for applications in drug delivery and regenerative medicine. |
| Databáze: | OpenAIRE |
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