Surprising Antibacterial Activity and Selectivity of Hydrophilic Polyphosphoniums Featuring Sugar and Hydroxy Substituents

Angew Chem Int Ed Engl. 2018 Sep 24;57(39):12707-12710. doi: 10.1002/anie.201806412. Epub 2018 Aug 30.

Abstract

There is currently an urgent need for the development of new antibacterial agents to combat the spread of antibiotic-resistant bacteria. We explored the synthesis and antibacterial activities of novel, sugar-functionalized phosphonium polymers. While these compounds exhibited antibacterial activity, we unexpectedly found that the control polymer poly(tris(hydroxypropyl)vinylbenzylphosphonium chloride) showed very high activity against both Gram-negative Escherichia coli and Gram-positive Staphylococcus aureus and very low haemolytic activity against red blood cells. These results challenge the conventional wisdom in the field that lipophilic alkyl substituents are required for high antibacterial activity and opens prospects for new classes of antibacterial polymers.

Keywords: antimicrobial agents; carbohydrates; haemolysis; phosphonium; polymers.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemistry*
  • Anti-Bacterial Agents / pharmacology
  • Escherichia coli / drug effects
  • Hemolysis / drug effects
  • Hydrophobic and Hydrophilic Interactions
  • Microbial Sensitivity Tests
  • Organophosphorus Compounds / chemistry
  • Polymers / chemical synthesis
  • Polymers / chemistry*
  • Polymers / pharmacology
  • Staphylococcus aureus / drug effects
  • Sugars / chemistry*
  • Vinyl Compounds / chemistry

Substances

  • Anti-Bacterial Agents
  • Organophosphorus Compounds
  • Polymers
  • Sugars
  • Vinyl Compounds
  • tributylmethyl phosphonium chloride