Ion conductors derived from biogenic amines, bile acids, and amino acids

A family of conjugates has been synthesized from spermine, putrescine, lysine, gamma-aminobutyric acid, sarcosine, cholic acid, glycocholic acid, 3alpha,7alpha-dihydroxycholic acid, and 3alpha,12alpha-dihydroxycholic acid, based on a design principle previously reported (Bandyopadhyay, P., Janout, V., Zhang, L., Regen, S. L. (2001) J. Am. Chem. Soc. 123, 7691). Each of these conjugates was found to exhibit significant activity in promoting the transport of Na(+) across liposomal membranes derived from 1,2-dimyristoleoyl-sn-glycero-3-phosphocholine, and also from 1,2-dipalmitoleoyl-sn-glycero-3-phosphocholine. In all cases, plots of pseudo first-order rate constants, k(obsd) vs (mol % of ion conductor)(2) were found to be linear, indicating that transport-active dimers are involved and that only a small fraction of the conjugates are in an aggregated form. An operational comparison that has been made within this series of conjugates indicates that Na(+) transport activity and membrane selectivity have a moderate dependency on the composition and the structure of the ion conductor.