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Supramolecularly constructing multifunctional platform for drug delivery is a challenging task. In this work, we propose a novel supramolecular strategy 'drug chaperone', in which macrocyclic amphiphiles directly coassemble with cationic drugs into a multifunctional platform and its surface is further decorated with targeting ligands through host-guest recognition. The coassembling and hierarchical decoration processes were monitored by optical transmittance measurements, and the size and morphology of amphiphilic coassemblies were identified by dynamic light scattering and high-resolution transmission electron microscopy. In cell experiments to validate the drug chaperone strategy, the anticancer activities of free drugs were pronouncedly improved by coassembling with amphiphilic chaperone and further functionalization with targeting ligand. [ABSTRACT FROM AUTHOR]