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Synthesis and membrane activity of a bis(metacyclophane)bolaamphiphile
Lynn M Cameron1, Thomas M Fyles, Chi-wei Hu
1Department of Chemistry, University of Victoria, Victoria, British Columbia, Canada V8W 3P6.
The Journal of Organic Chemistry
|March 2, 2002
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.