Ultimately, self-assembling amphiphiles may provide a unique solution to achieve enhanced solubility within both aqueous and lipid environments, as assembled structures can shield either the hydrophobic or hydrophilic regions respectively depending on the local environment. One such class of supramolecular self-associating amphiphiles (SSAs) was developed by and in this report, we aimed to investigate SSAs as candidate water-soluble cation transporters. Several key structural components were considered for the successful design, including a sulfonate group to enhance both water-solubility and cation binding, whilst the inclusion of a urea moiety may promote self-assembly within lipophilic environments via hydrogen bonding. Furthermore, published experiments have shown the penetration of SSAs through bacterial and cancer-cell membranes despite their ionic character. Recent studies have established that intrinsically fluorescent, benzothiazole substituted SSAs 1 and 2 (Figure ), display aggregation-dependent antimicrobial activity against both Gram-positive MRSA USA300 and Gram-negative bacteria Escherichia coli (E. coli) DH10beta. In particular, SSA 2 has been observed to coat and penetrate both bacterial cell and cancer cell membranes in fluorescence microscopy experiments. Ultimately, understanding the deliverability and ion-transport properties of SSAs may shed light on the mechanism of their biological activity as antimicrobial agents 13b and efficacy enhancers for both anticancer and antimicrobial agents. Figure The structures of SSAs 1-3 and anionophore 4 used in this study. TBA is [ntetrabutylammonium] + .