N-(furfural) chitosan hydrogels based on Diels–Alder cycloadditions and application as microspheres for controlled drug release

Marcelino Montiel-Herrera, Alessandro Gandini, Francisco M. Goycoolea, Niel Jacobsen, Jaime Lizardi-Mendoza, Maricarmen Recillas-Mota, Waldo Argüelles-Monal

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72 Scopus citations

Abstract

In this study, chitosan was chemically modified by reductive amination in a two-step process. The synthesis of N-(furfural) chitosan (FC) was confirmed by FT-IR and 1H 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 electron 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.

Original languageAmerican English
Article number128
Pages (from-to)220-227
Number of pages7
JournalCarbohydrate Polymers
Volume128
DOIs
StatePublished - 2015

Bibliographical note

Publisher Copyright:
© 2015 Elsevier Ltd. All rights reserved.

Keywords

  • Chitosan
  • Click chemistry
  • Diels-Alder
  • Furans
  • Hydrogels
  • Reductive amination

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