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Paper | Special issue | Vol 73, No. 1, 2007, pp.825-839
Published online, 2nd October, 2007
DOI: 10.3987/COM-07-S(U)62
Heterocyclic Amide Hydraphile Synthetic Cation Transporters

Wei Wang, Carl R. Yamnitz, and George W. Gokel*

*Departments of Chemistry & Biochemistry and Biology, Center for Nanoscience, University of Missouri - Saint Louis, One University Boulevard, Saint Louis, MO 63121 USA

Abstract

A family of hydraphile ionophores has been prepared in which various ~CH2N~ to ~CON~ replacements have been made to assess the effect on Na+ transport through phospholipid bilayers. When the central relay (see graphical abstract) was a third macrocycle, symmetrical carbonyl for methylene replacements enhanced activity, but the presence of four or six amide residues diminished transport. When a pair of amides was incorporated into compounds having a 4,4‘-bipiperidyl central relay, both significant increases and decreases were observed depending upon the amide positions. The presence of amides alters both the donor group type and strength and the conformation of the structural unit in which it occurs. These changes are shown to depend on the liposomes in which the Na+ release studies were conducted. These changes are shown to affect the toxicity of the hydraphiles to E. coli.