N-(furfural) chitosan hydrogels based on Diels–Alder cycloadditions and application as microspheres for controlled drug release
| Autor: | Neil E. Jacobsen, Jaime Lizardi-Mendoza, Francisco M. Goycoolea, Alessandro Gandini, Waldo Argüelles-Monal, Marcelino Montiel-Herrera, Maricarmen T. Recillas-Mota |
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| Rok vydání: | 2015 |
| Předmět: |
Magnetic Resonance Spectroscopy
Polymers and Plastics Kinetics Furfural Reductive amination Maleimides Chitosan chemistry.chemical_compound Spectroscopy Fourier Transform Infrared Polymer chemistry Materials Chemistry Furaldehyde chemistry.chemical_classification Cycloaddition Reaction Organic Chemistry Hydrogels Polymer Microspheres chemistry Delayed-Action Preparations Self-healing hydrogels Click chemistry Click Chemistry Methylene blue Nuclear chemistry |
| Zdroj: | Carbohydrate Polymers. 128:220-227 |
| ISSN: | 0144-8617 |
| DOI: | 10.1016/j.carbpol.2015.03.052 |
| Popis: | a b s t r a c t In this study, chitosan was chemically modified by reductive amination in a two-step process. The syn- thesis of N-(furfural) chitosan (FC) was confirmed by FT-IR and 1 H NMR analysis, and the degrees of substitution were estimated as 8.3 and 23.8%. The cross-linkable system of bismaleimide (BM) and FC shows that FC shared properties of furan-maleimide chemistry. This system produced non-reversible hydrogel networks by Diels-Alder cycloadditions at 85 ◦C. The system composed of BM and FC (23.8% substitution) generated stronger hydrogel networks than those of FC with an 8.3% degree of substitution. Moreover, the FC-BM system was able to produce hydrogel microspheres. Environmental scanning elec- tron microscopy revealed the surface of the microspheres to be non-porous with small protuberances. In water, the microspheres swelled, increasing their volume by 30%. Finally, microspheres loaded with methylene blue were able to release the dye gradually, obeying second-order kinetics for times less than 600 min. This behavior suggests that diffusion is governed by the relaxation of polymer chains in the swelled state, thus facilitating drug release outside the microspheres. |
| Databáze: | OpenAIRE |
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