Click synthesis of quaternized poly(dimethylaminoethyl methacrylate) functionalized graphene oxide with improved antibacterial and antifouling ability

Colloids Surf B Biointerfaces. 2016 May 1:141:196-205. doi: 10.1016/j.colsurfb.2016.01.046. Epub 2016 Jan 29.

Abstract

A quaternized poly(dimethylaminoethyl methacrylate) functionalized graphene oxide (GO-QPDMAEMA) was successfully prepared in this study via click chemistry. Alkyne-functionalized graphene oxide (GO-alkyne) was first synthesized through a two-step amidation reaction of GO-COOH. Meanwhile, azide-terminated poly(dimethylaminoethyl methacrylate) (PDMAEMA-N3) was prepared via the atom-transfer radical-polymerization of dimethylaminoethyl methacrylate (DMAEMA). Subsequently, PDMAEMA-N3 was grafted onto the GO-alkyne through click chemistry to obtain PDMAEMA modified graphene oxide (GO-PDMAEMA). Finally, the tertiary amino groups of GO-PDMAEMA were quaternized by ethyl bromide to provide a quaternized poly(dimethylaminoethyl methacrylate) functionalized graphene oxide (GO-QPDMAEMA). Various characterization techniques, including Fourier-transform infrared spectroscopy, X-ray photoelectron spectroscopy, UV-vis spectrometry, ζ potential, Raman, contact angle analyses and field emission scanning electron microscope were used to ascertain the successful preparation of the quaternized GO-QPDMAEMA. Furthermore, antibacterial and antifouling activities of GO-QPDMAEMA were investigated via protein adsorption, as well as bacterial and cell adhesion studies. The results suggest that the GO-QPDMAEMA surface exhibited significant antibacterial and antifouling properties, compared with the GO-COOH and GO-PDMAEMA surfaces.

Keywords: Antibacterial; Antifouling; Click chemistry; Graphene oxide; Quaternary ammonium.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • A549 Cells
  • Anti-Bacterial Agents / chemistry*
  • Anti-Bacterial Agents / pharmacology
  • Bacterial Adhesion / drug effects
  • Biofouling / prevention & control
  • Cell Adhesion / drug effects
  • Cells, Cultured
  • Click Chemistry
  • Drug Carriers / chemistry
  • Escherichia coli / drug effects
  • Escherichia coli / physiology
  • Graphite / chemistry*
  • Graphite / pharmacology
  • HeLa Cells
  • Human Umbilical Vein Endothelial Cells / drug effects
  • Human Umbilical Vein Endothelial Cells / physiology
  • Humans
  • Methacrylates / chemistry*
  • Microscopy, Electron, Scanning
  • Molecular Structure
  • Nylons / chemistry*
  • Oxides / chemistry*
  • Oxides / pharmacology
  • Photoelectron Spectroscopy
  • Spectrophotometry
  • Spectroscopy, Fourier Transform Infrared
  • Staphylococcus aureus / drug effects
  • Staphylococcus aureus / physiology

Substances

  • Anti-Bacterial Agents
  • Drug Carriers
  • Methacrylates
  • Nylons
  • Oxides
  • poly(2-(dimethylamino)ethyl methacrylate)
  • Graphite