Design, synthesis and characterization of acyclic bola-amphiphiles that form ion channels
Date
2001
Authors
Eggers, Paul Kahu
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Abstract
A demacrocyclization design strategy for the creation of ion channel-forming compounds was explored. Beginning with an active bis-macrocyclic bola-amphiphile, two and four tailed acyclic bola-amphiphiles were identified. These target compounds were prepared by a modular synthetic approach based on ester and amide linking reactions resulting in an increased overall yield from previous macrocyclic compounds. Transport activity was measured by pH-stat titration methods. All three compounds exhibited significantly high activity. The compound containing central esters was clearly less active than the compounds containing central amides. All compounds are apparently strongly partitioned to a vesicle bilayer membrane.