Herein, we present a series of four novel amino acid appended SSAs (Figure -3, 5, 7, and 9) designed to selectively increase the activity of this class of compound against drug susceptible and resistant S. aureus and ovarian cancer cells. The design of these next generation SSAs: (i) builds on current structure activity relationship analysis, which suggests that the presence of a carboxylate functionality within the structure of the SSA anion increases the strength of preferential intermolecular interactions; (ii) explores the effects of chirality on SSA (host) biological activity, as phospholipid headgroups can act as chiral guest species, during initial biological membrane interaction events; (iii) use the presence of a hydrophobic amino acid R-group to increase the stability of any SSA transmembrane structures within the hydrophobic portions of the phospholipid bilayer through shielding of the SSA anion hydrophilic moieties (3, 5, 7, 9), and/or introducing π-π stacking interactions (7 and 9).