Development of Gallic Acid-Modified Hydrogels Using Interpenetrating Chitosan Network and Evaluation of Their Antioxidant Activity

Molecules. 2017 Nov 15;22(11):1976. doi: 10.3390/molecules22111976.

Abstract

In this work, antioxidant hydrogels were prepared by the construction of an interpenetrating chitosan network and functionalization with gallic acid. The poly(2-hydroxyethyl methacrylate) p(HEMA)-based hydrogels were first synthesized and subsequently surface-modified with an interpenetrating polymer network (IPN) structure prepared with methacrylamide chitosan via free radical polymerization. The resulting chitosan-IPN hydrogels were surface-functionalized with gallic acid through an amide coupling reaction, which afforded the antioxidant hydrogels. Notably, gallic-acid-modified hydrogels based on a longer chitosan backbone exhibited superior antioxidant activity than their counterpart with a shorter chitosan moiety; this correlated to the amount of gallic acid attached to the chitosan backbone. Moreover, the surface contact angles of the chitosan-modified hydrogels decreased, indicating that surface functionalization of the hydrogels with chitosan-IPN increased the wettability because of the presence of the hydrophilic chitosan network chain. Our study indicates that chitosan-IPN hydrogels may facilitate the development of applications in biomedical devices and ophthalmic materials.

Keywords: IPN; antioxidant activity; chitosan; gallic acid; hydrogels.

MeSH terms

  • Antioxidants / chemistry
  • Antioxidants / pharmacology*
  • Chitosan / chemistry
  • Gallic Acid / chemistry*
  • Hydrogels / chemistry
  • Hydrogels / pharmacology*
  • Molecular Structure
  • Polyamines / chemistry
  • Polyhydroxyethyl Methacrylate / analogs & derivatives
  • Polyhydroxyethyl Methacrylate / chemistry
  • Surface Properties
  • Wettability

Substances

  • Antioxidants
  • Hydrogels
  • Polyamines
  • poly(2-hydroxyethyl methacrylate)-polyamine graft copolymer
  • Polyhydroxyethyl Methacrylate
  • Gallic Acid
  • Chitosan