Biocompatible pillararene-assembly-based carriers for dual bioimaging

Abstract

Present research provides a successful example to use biocompatible pillararene-based assemblies for delivering mixed dyes in dual bioimaging. A series of tadpole-like and bola amphiphilic pillararenes 1–4 were synthesized by selectively employing water-soluble ethylene glycols and hydrophobic alkyl units as the starting materials. In comparison with their monomers, these amphiphilic pillararenes not only show improved biocompatibility to cells but also could form homogeneous supramolecular self-assemblies. Interestingly, different types of amphiphilic pillararene-based assemblies exhibit various performances on the delivery of dyes with different aqueous solubility. All assemblies can deliver water-soluble rhodamine B to cells, while only tadpole-like amphiphilic pillararene-based assemblies performed better on delivering hydrophobic fluorescein isothiocyanate for imaging. In addition, pillararene derivatives 1, 3, and 4 could complex with a viologen guest, further forming stable assemblies for bioimaging. In such cases, the assembly formed from the complex of tadpole-like amphiphile pillararene 1 with the viologen guest performed better in delivering mixed dyes. Finally, an anticancer drug, doxorubicin, was successfully delivered to cells by using the pillararene-based assemblies. The current research has determined the capacities of pillararene-based assemblies to deliver different dyes for bioimaging and paves the way for using these biocompatible carriers toward combined cancer therapy.