Antifouling Activities of Immobilized Ferrocenyl Glucose on a Glassy Carbon Surface

ACS Appl Mater Interfaces. 2020 Jul 22;12(29):33370-33376. doi: 10.1021/acsami.0c06859. Epub 2020 Jul 10.

Abstract

Polar coatings are used to protect surfaces from marine fouling based on the formation of a hydrated surface layer, which acts as a barrier to marine microorganisms. In this context, we have developed a material with glucose bound to ferrocene to prevent surface absorption. Glucose brings the polarity while ferrocene has the role of varying the state of charge of the surface. We therefore describe the synthesis of 6-deoxy-6-(4-ferrocenyl-1H-1,2,3-triazol-1-yl)-1-(4-aminophenyl)-β-D-glucopyranose 6 and its immobilization on the surface of a C electrode and develop a methodology used for antibacterial testing. We were able to demonstrate that the immobilization of glucose 6 could be done in an artificial seawater environment by oxidation of an amine. The use of a 96-microwell platform equipped with electrodes for cyclic voltammetry, linked to a potentiostat, allowed the electrical solicitation of the coating in the presence of marine bacteria with a greater number of biological replicates. We have shown that the coating has an antibacterial effect, and this effect is accentuated when the coating is electrically stressed, resulting in the appearance and disappearance of charge on ferrocene, a phenomenon that seems to be conducive to colonization by bacteria.

Keywords: amine oxidation; antifouling; electroactivity; ferrocene.

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology*
  • Bacterial Adhesion / drug effects
  • Biofilms / drug effects*
  • Carbon / chemistry*
  • Electrochemical Techniques
  • Electrodes
  • Ferrous Compounds / chemistry*
  • Glass / chemistry
  • Glucose / chemistry*
  • Metallocenes / chemistry*
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Particle Size
  • Pseudoalteromonas / drug effects*
  • Surface Properties

Substances

  • Anti-Bacterial Agents
  • Ferrous Compounds
  • Metallocenes
  • Carbon
  • Glucose
  • ferrocene

Supplementary concepts

  • Pseudoalteromonas lipolytica