Assembly of a Succinyl Acid Calix[4]arene Derivative in a Multilamellar Vesicle and a Preliminary Study of a Hydrophobic and Hydrophilic Guest Loading

Calixarenes are very attractiveplatforms in the development of amphiphilic derivatives encoded to aggregate in higher order supramolecular architectures with a variegated level of structural complexity.1 In this work we report that an amphiphilic calix[4]arene derivative (1), bearing four terminal carboxylic acid groups at the calixarene upper rim and dodecyl chains at the lower rim, forms discrete and very stable nanoaggregates in aqueous medium. Field Emission Scanning Electron Microscopy (FE-SEM) and Transmission Electron Microscopy (TEM) images show that the aggregates of 1 possess a spherical shape and a vesicular structure with a multilamellar wall. The vesicle of 1 encapsulates a hydrophilic dye (rodhamine B) in its aqueous lumen, and increases water-solubility of a hydrophobic drug such as curcumin. These results open perspectives for application of the amphiphilic calix[4]arene derivative (1) as a drug delivery system.2 Figure 1.Amphiphilic calix[4]arene derivative 1, FE-SEM and TEM images, and a schematic representation of the hypothesized multilamellar structure. 1 Helttunen, K.; Shahgaldian P. New J. Chem. 2010, 34, 2704-2714. 2 Zhou, Y.; Li, H.; Yang,Y.-W. Chinese Chemical Letters in press.