Synthesis of 3,4-dihydroxyphenylalanine (DOPA) containing monomers and their co-polymerization with PEG-diacrylate to form hydrogels

Bruce P. Lee, Kui Huang, F. Nelson Nunalee, Kenneth Shull, Phillip B. Messersmith*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

89 Scopus citations

Abstract

L-3,4-Dihydroxyphenylalanine (DOPA) is an unusual amino acid found in mussel adhesive proteins (MAPs) that is believed to lend adhesive characteristics to these proteins. Most previous efforts to incorporate DOPA into hydrogels have utilized oxidative cross-linking, which is hypothesized to reduce the adhesive properties of DOPA and requires reagents that are harmful to biological tissues. In this paper, we describe the synthesis of N-methacrylated DOPA monomers and their copolymerization with poly(ethylene glycol) diacrylate (PEG-DA) using either ultraviolet (UV) or visible light. The effect of DOPA containing monomers on gelation time, gel conversion and elastic modulus of the photocured hydrogels was investigated. Despite a retarding effect of DOPA on photopolymerization, DOPA was successfully incorporated into hydrogels with elastic moduli suitable for many biomedical applications. The incorporation of DOPA into hydrogels by photopolymerization may lead to new adhesive hydrogels for medical applications.

Original languageEnglish (US)
Pages (from-to)449-464
Number of pages16
JournalJournal of Biomaterials Science, Polymer Edition
Volume15
Issue number4
DOIs
StatePublished - 2004

Keywords

  • Bioadhesive
  • Contact mechanics
  • DMPA
  • DOPA
  • Hydrogel
  • Photopolymerization
  • Poly(ethylene glycol)

ASJC Scopus subject areas

  • Biophysics
  • Bioengineering
  • Biomaterials
  • Biomedical Engineering

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