Synthesis of zwitterionic N-chlorohydantoins for antibacterial applications

Bioorg Med Chem Lett. 2018 Dec 15;28(23-24):3665-3669. doi: 10.1016/j.bmcl.2018.10.034. Epub 2018 Oct 23.

Abstract

Two novel zwitterionic N-chlorohydantoin biocides, containing an N-chlorohydantoin unit and a sulfobetaine unit or a carboxybetaine unit, were chemically synthesized and characterized. Using the quaternary ammonium N-chlorohydantoin as control, the antibacterial activity of synthetic zwitterionic N-chlorohydantoins was challenged and the antibacterial data showed that carboxybetaine N-chlorohydantoin exhibited distinctively higher biocidal efficacy than QA counterpart, while sulfobetaine N-chlorohydantoin displayed slightly inferior antimicrobial efficacy. Our results may inspire further exploration of more zwitterionic N-chlorohydantoin analogs for antibacterial application.

Keywords: Antibacterial application; Chemical synthesis; N-chlorohydantoins; Zwitterionic compounds.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology
  • Betaine / analogs & derivatives*
  • Betaine / chemistry
  • Cell Wall / metabolism
  • Escherichia coli / drug effects
  • Magnetic Resonance Spectroscopy
  • Quaternary Ammonium Compounds / chemistry
  • Staphylococcus aureus / drug effects

Substances

  • Anti-Bacterial Agents
  • Quaternary Ammonium Compounds
  • Betaine
  • sulfobetaine