The field of supramolecular chemistry, although young in comparison to the field of medicinal chemistry, is making a considerable effort to exploit our understanding of molecular interactions in the production of next-generation approaches to the design of anticancer and antimicrobial technologies. Supramolecular self-associating amphiphiles (SSAs) are a class of amphiphilic salts (Figure ) and structurally related compounds that are capable of undergoing intermolecular hydrogen bonding events. These events not only influence SSA selfassociative properties and any resultant material formation (hydrogels or spherical aggregate), but also the interaction of this class of compounds with other molecular species, such as cell surfaces, in particular phospholipid membranes. We have previously shown SSAs to demonstrate activity as both antimicrobial agents against Gram-positive methicillin resistant Staphylococcus aureus (MRSA) USA300 and Gram-negative Escherichia coli, as well as against A2780 ovarian cancer cells. In addition, we have shown that members from this family of compounds have a druggable profile when administered intravenously to mice, although Caco-2 permeability studies have suggested to date that SSAs may only be developed as therapeutic agents to be administered intravenously. Figure Structures of five amino acid incorporated SSAs (1, 3, 5, 7 and 9) and precursors (2, 4, 6 and 8). Each SSA was prepared as the tetrabutylammonium (TBA) salt.