Synthesis and antibacterial activity of quaternary ammonium salt-type antibacterial agents with a phosphate group

J Oleo Sci. 2008;57(8):445-52. doi: 10.5650/jos.57.445.


Quaternary ammonium salts are frequently used as antibacterial agent that disrupts cell membrane through the binding of their ammonium cations to anionic sites in the outer layer tissue of bacteria. This article describes the synthesis of quaternary ammonium salt-type antibacterial agents with a phosphate group that strongly binds to hydroxyapatite and bromide ion as counterion. Evaluation of the antibacterial activity of the synthesized compounds in terms of minimum inhibitory concentration (MIC test) showed that the compounds exhibit an excellent antibacterial activity on a variety of bacteria including Gram-positive and Gram-negative bacteria, yeast, and fungi.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / pharmacology*
  • Antifungal Agents / chemical synthesis
  • Antifungal Agents / pharmacology*
  • Binding Sites
  • Bromides / chemistry
  • Bromides / metabolism
  • Cell Membrane / chemistry
  • Cell Membrane / metabolism
  • Durapatite / chemistry
  • Durapatite / metabolism
  • Fungi / drug effects*
  • Gram-Negative Bacteria / drug effects*
  • Gram-Positive Bacteria / drug effects*
  • Microbial Sensitivity Tests
  • Phosphates / chemistry*
  • Phosphates / metabolism
  • Quaternary Ammonium Compounds / chemical synthesis
  • Quaternary Ammonium Compounds / pharmacology*
  • Structure-Activity Relationship


  • Anti-Bacterial Agents
  • Antifungal Agents
  • Bromides
  • Phosphates
  • Quaternary Ammonium Compounds
  • Durapatite