Telechelic, Antimicrobial Hydrophilic Polycations with Two Modes of Action

Macromol Biosci. 2018 Apr;18(4):e1700389. doi: 10.1002/mabi.201700389. Epub 2018 Mar 7.

Abstract

Telechelic antimicrobial poly(2-oxazoline)s with quaternary ammonium (quat) end groups are shown to be potent antimicrobial polymers against Gram-positive bacterial strains. In this study, the activity against the Gram-negative bacterium Escherichia coli is additionally implemented by hydrolyzing the poly(2-methyl-2-oxazoline) with two quart end groups to poly(ethylene imine) (PEI). The resulting telechelic polycations are active against Staphylococcus aureus and E. coli. The contribution of the PEI backbone is determined by measuring the antimicrobial activity in the presence of calcium ions. The influence of PEI on the overall activity strongly depends on the molecular weight and increases with higher mass. The PEI dominates the activity against E. coli at lower masses than against S. aureus. The quart end groups require an alkyl substituent of dodecyl or longer to dominate the antimicrobial activity. Additionally, PEI and quart end groups act synergistically.

Keywords: antimicrobial polymer; poly(2-oxazoline); poly(ethylene imine); telechelic.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Infective Agents / chemical synthesis
  • Anti-Infective Agents / chemistry
  • Anti-Infective Agents / pharmacology*
  • Calcium / metabolism
  • Escherichia coli / drug effects*
  • Escherichia coli / pathogenicity
  • Humans
  • Hydrophobic and Hydrophilic Interactions
  • Imines / chemical synthesis
  • Imines / chemistry
  • Imines / pharmacology
  • Microbial Sensitivity Tests
  • Oxazoles / chemical synthesis
  • Oxazoles / chemistry
  • Oxazoles / pharmacology*
  • Polyethylenes / chemical synthesis
  • Polyethylenes / chemistry
  • Polyethylenes / pharmacology
  • Polymers / chemical synthesis
  • Polymers / chemistry
  • Staphylococcus aureus / drug effects*
  • Staphylococcus aureus / pathogenicity

Substances

  • 2-methyl-2-oxazoline
  • Anti-Infective Agents
  • Imines
  • Oxazoles
  • Polyethylenes
  • Polymers
  • poly(ethylene imine)
  • Calcium