Synthetic Channel Specifically Inserts into the Lipid Bilayer of Gram-Positive Bacteria but not that of Mammalian Erythrocytes

Angew Chem Int Ed Engl. 2017 Mar 6;56(11):2999-3003. doi: 10.1002/anie.201612093. Epub 2017 Feb 7.

Abstract

A series of tubular molecules with different lengths have been synthesized by attaching Trp-incorporated peptides to the pillar[5]arene backbone. The tubular molecules are able to insert into the lipid bilayer to form unimolecular transmembrane channels. One of the channels has been revealed to specifically insert into the bilayer of the Gram-positive bacteria. In contrast, this channel cannot insert into the membranes of the mammalian rat erythrocytes even at the high concentration of 100 μm. It was further demonstrated that, as a result of this high membrane selectivity, the channel exhibits efficient antimicrobial activity for the Gram-positive bacteria and very low hemolytic toxicity for mammalian erythrocytes.

Keywords: antimicrobial activity; hemolytic toxicity; lipid bilayers; pillar[5]arenes; synthetic channels.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Calixarenes / chemistry*
  • Calixarenes / metabolism
  • Calixarenes / pharmacology
  • Erythrocytes / drug effects
  • Humans
  • Lipid Bilayers / chemistry*
  • Lipid Bilayers / metabolism
  • Molecular Structure
  • Particle Size
  • Peptides / chemistry*
  • Peptides / metabolism
  • Peptides / pharmacology
  • Staphylococcus epidermidis / chemistry*
  • Staphylococcus epidermidis / cytology
  • Staphylococcus epidermidis / metabolism
  • Surface Properties

Substances

  • Lipid Bilayers
  • Peptides
  • pillar(5)arene
  • Calixarenes