We have previously shown members from the wider SSA library to exhibit activity against Gram-positive, clinically relevant MRSA USA300 and the A2780 cisplatin susceptible ovarian cancer cell line. During these studies, data obtained from live cell fluorescence microscopy experiments showed intrinsically fluorescent SSAs arriving at the cells surface as spherical aggregates, then forming a coating over the surface of the cell, diffusing across the cell surface membranes, before becoming internalised within the cell and moving to interact with those structures within the cell itself. We had also shown SSAs to selectively interact with phospholipid membranes of differing composition, demonstrated the potential for members of the SSA library to be developed as drugs for intravenous administration. Within the scope of this study, we have built on initial structure activity relationships, incorporating chirality through the presence of both natural and unnatural amino acid residues into the SSA structure. Through comparison with the control achiral, glycine substituted 1, we have provided evidence that the incorporation of hydrophobic R-groups, alongside the introduction of chirality within the SSA scaffold and control of self-associative complexation processes significantly enhances both desirable biological activity against both infectious and non-infectious disease-causing cells.