In conclusion, we have reported an investigation of the ion transport activity for a series of supramolecular, self-associating amphiphiles with established antimicrobial and therapeutic enhancement activity. SSA 1 was found to enable both K + /Cl -and Na + /Cl -co-transport in combination with anionophore 4, whereas SSAs 2 and 3 were not found to mediate selective ion transport and may instead function as membrane disrupting agents. SSA 1 is a novel and water-soluble transport motif, demonstrating that charged amphiphiles can have promising deliverability prospects and address major concerns in the development of synthetic ionophores for medicinal applications. We propose that this membrane permeabilisation may be partially responsible for the established biological activity of SSA 1, as it could function in combination with native biological transport proteins. Our findings also suggest that ionophoric activity is not a generalisable observation across this class of SSAs, which is in line with previous findings that SSAs 1 and 2 exhibit different biological activities and membrane adhesive properties.