Synthesis and membrane activity of a bis(metacyclophane)bolaamphiphile.
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.
Cameron
Lynn M
LM
Department of Chemistry, University of Victoria, Victoria, British Columbia, Canada V8W 3P6.
Fyles
Thomas M
TM
Hu
Chi-wei
CW
D001692:Biological Transport; D004988:Ethers, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D007473:Ion Channels / Q000737:chemistry* / Q000378:metabolism; D008051:Lipid Bilayers / Q000737:chemistry*; D047028:Macrocyclic Compounds; D009682:Magnetic Resonance Spectroscopy; D008564:Membrane Potentials; D008566:Membranes / Q000737:chemistry* / Q000378:metabolism; D008958:Models, Molecular; D015394:Molecular Structure; D010713:Phosphatidylcholines / Q000737:chemistry*; D010795:Phthalic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D013329:Structure-Activity Relationship
D004988:Ethers, Cyclic; D007473:Ion Channels; D008051:Lipid Bilayers; D047028:Macrocyclic Compounds; D010713:Phosphatidylcholines; D010795:Phthalic Acids; C452303:bis(metacyclophane)bolaamphiphile