Synthesis and membrane activity of a bis(metacyclophane)bolaamphiphile

J Org Chem. 2002 Mar 8;67(5):1548-53. doi: 10.1021/jo0160930.

Abstract

The synthesis of macrocyclic tetraesters from 5-substituted isophthalic acids and 1,8-octane diol gave macrocylic metacyclophanes with the axially symmetric positions differentially protected. Dimer bis(metacyclophane)bolaamphiphiles proved to be extremely insoluble, but one derivative was shown to have significant membrane activity. Very high continuous conductance and the formation of discrete single-ion channels were both observed, depending on how the compound was incorporated into the bilayer membrane.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biological Transport
  • Ethers, Cyclic / chemical synthesis*
  • Ethers, Cyclic / chemistry
  • Ion Channels / chemistry*
  • Ion Channels / metabolism
  • Lipid Bilayers / chemistry*
  • Macrocyclic Compounds*
  • Magnetic Resonance Spectroscopy
  • Membrane Potentials
  • Membranes / chemistry*
  • Membranes / metabolism
  • Models, Molecular
  • Molecular Structure
  • Phosphatidylcholines / chemistry*
  • Phthalic Acids / chemical synthesis*
  • Phthalic Acids / chemistry
  • Structure-Activity Relationship

Substances

  • Ethers, Cyclic
  • Ion Channels
  • Lipid Bilayers
  • Macrocyclic Compounds
  • Phosphatidylcholines
  • Phthalic Acids
  • bis(metacyclophane)bolaamphiphile