Interaction of triclosan with eukaryotic membrane lipids

Eur J Oral Sci. 2003 Jun;111(3):216-22. doi: 10.1034/j.1600-0722.2003.00034.x.

Abstract

The possibility that triclosan and PVM/MA (polyvinylmethyl ether/maleic acid) copolymer, additives to dentrifrices, could interact with eukaryotic membrane lipids was studied by two methods: first, by determining the pressure/molecular area isotherms at 37 degrees C of glycerophospholipid monolayers, using the Langmuir technique; and second, by phase-transition parameters in liposomes of the same lipids, using differential scanning calorimetry (DSC). Triclosan interacted, in a concentration-independent manner, with monolayers of saturated phosphatidylcholines (PC; i.e. markers of the outer membrane leaflet of eukaryotic cells). Triclosan and PVM/MA copolymer mixtures were shown to clearly interact in a concentration-dependent manner with PC. Triclosan was found to interact with liposomes of saturated and unsaturated phosphatidylcholines and phosphatidylserines (PS; i.e. markers of the inner membrane leaflet of eukaryotic cells), and saturated ethanolamines (PE; i.e. markers of the inner membrane leaflet of eukaryotic cells), resulting in a decrease of the lipid melting temperature (Tm). PVM/MA copolymer changed the Tm of PS, PC, and PE in different manners. By adding PVM/MA or triclosan-PVM/MA copolymer mixtures to 1-stearoyl-2-oleoyl-sn-glycero-3-phosphoserine (SOPS) no lipid transitions were detected. A biphasic change of the PC transition temperature resulted when triclosan or triclosan PVM/MA copolymer mixtures were added, indicating domain formation and change of the lipid polymorphism.

MeSH terms

  • Anti-Infective Agents, Local / pharmacokinetics
  • Anti-Infective Agents, Local / pharmacology*
  • Calorimetry, Differential Scanning
  • Cell Membrane / drug effects*
  • Cell Membrane / metabolism
  • Dose-Response Relationship, Drug
  • Eukaryotic Cells / drug effects
  • Eukaryotic Cells / metabolism
  • Glycerophospholipids / chemistry
  • Glycerophospholipids / metabolism*
  • Liposomes / chemistry
  • Liposomes / metabolism
  • Maleates / pharmacokinetics
  • Maleates / pharmacology
  • Membrane Lipids / chemistry
  • Membrane Lipids / metabolism*
  • Models, Chemical
  • Phosphatidylcholines / chemistry
  • Phosphatidylcholines / metabolism
  • Phosphatidylserines / chemistry
  • Phosphatidylserines / metabolism
  • Polyethylenes / pharmacokinetics
  • Polyethylenes / pharmacology
  • Triclosan / pharmacokinetics
  • Triclosan / pharmacology*

Substances

  • Anti-Infective Agents, Local
  • Glycerophospholipids
  • Liposomes
  • Maleates
  • Membrane Lipids
  • Phosphatidylcholines
  • Phosphatidylserines
  • Polyethylenes
  • Triclosan
  • poly(methyl vinyl ether-co-maleic anhydride)