Morphology Control in Supramolecular Assemblies of Sulfated π-Amphiphiles and Impact on the Antiviral Activity

This manuscript reports H-bonding regulated morphology control in aqueous supramolecular assemblies of naphthalene-diimide (NDI)-derived sulfated amphiphiles and its direct correlation with antiviral activity. NDI-1 with a hydrazide group produces a polymersome structure with an efficient display of the sulfate groups on the outer surface, resulting in excellent antiviral activity by a fusion mechanism. NDI-3 lacking any H-bonding group or NDI-2 having the amide group produces particle-like or worm-like structures, respectively, with significantly low antiviral activity. Confocal microscopy images show that NDI-1 is able to fully deactivate and stop the entry of the virus to a host cell, indicating its great promise for future medicinal use, especially as it exhibits negligible toxicity toward a mammalian cell.