The synthesis and membrane activity of linear oligoester, ester-Amide, and oligoamide bolaamphiphiles

Abstract

The synthesis of four new ester- and amide-containing linear bolaamphiphiles is described. The ability of these compounds to create ion channels in vesicle bilayer membranes, and their potential as membrane disrupting agents, was examined in vesicle bilayers. Compounds containing only ester linkages were inefficient membrane disrupting agents yet formed non-selective ion channels at low concentration. Compounds containing mixed ester and amide linkages were more effective membrane disrupting agents, which masked any low-level ion channel activity. A compound containing only amide linkages was inactive as either a disrupting agent or as an ion channel. This series confirms that ion channels can be formed by very simple oligoester acyclic bolaamphiphiles.