A Bolaamphiphilic and Nanoparticulate Pillar[6]arene for Noncovalent/Inclusion Complexation of Doxorubicin and Mitoxantrone in Water

High Resolution Image Download MS PowerPoint Slide Pillar[6]arene 1 2– is a dianionic and accessible host, possessing a cylindrical cavity composed of six benzene rings with ten ethoxy and two carboxylic acid groups at the top/bottom portals. The results from 1 H NMR spectroscopy, dynamic light scattering (DLS), scanning electron microscopy (SEM), and transmission electron microscopy (TEM) measurements of bolaamphiphilic 1 2– in 30 mM phosphate buffer (PBS) at pH = 7.4 are in line with its self-association into spherical nanoparticles at concentrations up to 200 μM. At lower concentrations ( y) along with (b) binary and inclusion [drug⊂pillararene] complexes. The existence of the latter was corroborated with mass spectrometry (ESI/TOF MS). Importantly, multimeric [drug x ⊂pillararene y ] and binary [drug⊂pillararene] complexes constitute sizable and spherical nanoparticles (600 nm–1 μm; DLS and TEM). With the biocompatibility of nanoparticulate 1 2– toward HeLa cells and its capacity to capture toxic anticancer agents used in clinics thereby forming larger nanoparticles, we reason that the nanosystem described here could be developed into a platform for effective sequestration or delivery of anticancer drugs.