Catecholamine-Copper Redox as a Basis for Site-Specific Single-Step Functionalization of Material Surfaces

ACS Appl Mater Interfaces. 2021 Jan 27;13(3):4711-4722. doi: 10.1021/acsami.0c19396. Epub 2021 Jan 14.

Abstract

Realization of robust and facile surface functionalization processes is critical to biomaterials and biotechnology yet remains a challenge. Here, we report a new chemical approach that enables operationally simple and site-specific surface functionalization. The mechanism involves a catechol-copper redox chemistry, where the oxidative polymerization of an alkynyl catecholamine reduces Cu(II) to Cu(I), which in situ catalyzes a click reaction with azide-containing molecules of interest (MOIs). This process enables drop-coating and grafting of two- and three-dimensional solid surfaces in a single operation using as small as sub-microliter volumes. Generalizability of the method is shown for immobilizing MOIs of diverse structure and chemical or biological activity. Biological applications in anti-biofouling, cellular adhesion, scaffold seeding, and tissue regeneration are demonstrated, in which the activities or fates of cells are site-specifically manipulated. This work advances surface chemistry by integrating simplicity and precision with multipurpose surface functionalization.

Keywords: antibacterial; catecholamine polymerization; cell adhesion; click reaction; surface patterning; tissue engineering.

MeSH terms

  • 3T3 Cells
  • Animals
  • Azides / chemical synthesis
  • Azides / chemistry*
  • Biocompatible Materials / chemical synthesis
  • Biocompatible Materials / chemistry*
  • Biofouling / prevention & control
  • Catalysis
  • Catecholamines / chemical synthesis
  • Catecholamines / chemistry*
  • Click Chemistry
  • Copper / chemistry*
  • Human Umbilical Vein Endothelial Cells
  • Humans
  • Mice
  • Oxidation-Reduction
  • Polymerization
  • Surface Properties

Substances

  • Azides
  • Biocompatible Materials
  • Catecholamines
  • Copper