Fabrication of Patterned Hydrogel Interfaces: Exploiting the Maleimide Group as a Dual Purpose Handle for Cross-Linking and Bioconjugation

Bioconjug Chem. 2020 May 20;31(5):1382-1391. doi: 10.1021/acs.bioconjchem.0c00108. Epub 2020 Apr 20.

Abstract

Functional hydrogels that can be obtained through facile fabrication procedures and subsequently modified using straightforward reagent-free methods are indispensable materials for biomedical applications such as sensing and diagnostics. Herein a novel hydrogel platform is obtained using polymeric precursors containing the maleimide functional group as a side chain. The maleimide groups play a dual role in fabrication of functional hydrogels. They enable photochemical cross-linking of the polymers to yield bulk and patterned hydrogels. Moreover, the maleimide group can be used as a handle for efficient functionalization using the thiol-maleimide conjugation and Diels-Alder cycloaddition click reactions. Obtained hydrogels are characterized in terms of their morphology, water uptake capacity, and functionalization. Micropatterned hydrogels are obtained under UV-irradiation using a photomask to obtain reactive micropatterns, which undergo facile functionalization upon treatment with thiol-containing functional molecules such as fluorescent dyes and bioactive ligands. The maleimide group also undergoes conjugation through the Diels-Alder reaction, where the attached molecule can be released through thermal treatment via the retro Diels-Alder reaction. The antibiofouling nature of these hydrogel micropatterns enables efficient ligand-directed biomolecular immobilization, as demonstrated by attachment of streptavidin-coated quantum dots.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cycloaddition Reaction
  • Fluorescent Dyes / chemistry
  • Hydrogels / chemistry*
  • Maleimides / chemistry*
  • Photochemical Processes
  • Polymers / chemistry
  • Sulfhydryl Compounds / chemistry
  • Water / chemistry

Substances

  • Fluorescent Dyes
  • Hydrogels
  • Maleimides
  • Polymers
  • Sulfhydryl Compounds
  • Water
  • maleimide