Green and non-leaching anti-bacterial and cytocompatible coating with build-in quaternary ammonium salt derived from methoxysilane functionalized soybean oil

Mater Sci Eng C Mater Biol Appl. 2019 Jun:99:887-899. doi: 10.1016/j.msec.2019.02.029. Epub 2019 Feb 12.

Abstract

Preparation and evaluation of non-leaching antimicrobial polymeric coatings, derived from soybean oil, against bacterial contamination of some metallic biomedical devices are described in this work. Cyclic carbonate derivative of soybean oil (CSBO) was subjected to the reaction with 3-aminopropyl trimethoxysilane to produce a methoxysilane functional soybean oil (Si-SBU) with urethane linkage. A quaternary ammonium salt containing fatty amide molecule with reactive siloxane moiety (Si-SBQ) was also synthesized from soybean oil. The antimicrobial coatings were prepared through sol-gel hydrolysis/condensation reactions of Si-SBU mixed with different concentrations of Si-SBQ under atmospheric moisture condition. The coatings demonstrated very good hardness (202-263 s-1) and superior adhesion strength (2.25-2.95 MPa) to aluminum plate as a model metallic substrate. The biological activities of these coatings were investigated against both fibroblast cells and microorganism strains of Meticillin-resistant S. aureus, P. aeruginosa, and C. albicans. The coatings showed excellent cytocompatibility as they could support growth and proliferation of fibroblast cells (95-98% viability) on their surface. Meanwhile, they showed a high bactericidal activity against all the selected microorganisms.

Keywords: Antimicrobials; Coating; Cyclic carbonate; Non-isocyanate; Poly(urethane-siloxane); Soybean oil.

MeSH terms

  • Animals
  • Anti-Bacterial Agents / pharmacology*
  • Candida albicans / drug effects
  • Cell Line
  • Cell Survival / drug effects
  • Chlorides / analysis
  • Coated Materials, Biocompatible / pharmacology*
  • Fibroblasts / cytology
  • Fibroblasts / drug effects
  • Green Chemistry Technology / methods*
  • Hardness
  • Methicillin-Resistant Staphylococcus aureus / drug effects
  • Mice
  • Microbial Sensitivity Tests
  • Proton Magnetic Resonance Spectroscopy
  • Pseudomonas aeruginosa / drug effects
  • Quaternary Ammonium Compounds / pharmacology*
  • Silanes / chemistry*
  • Silicon / analysis
  • Soybean Oil / chemistry*
  • Spectroscopy, Fourier Transform Infrared
  • Thermogravimetry

Substances

  • Anti-Bacterial Agents
  • Chlorides
  • Coated Materials, Biocompatible
  • Quaternary Ammonium Compounds
  • Silanes
  • Soybean Oil
  • Silicon