Supramolecular nanoassemblies of an amphiphilic porphyrin-cyclodextrin conjugate and their morphological transition from vesicle to network.

ABSTRACT

An amphiphilic compound, 5-(4'-dodecyloxyphenyl)-10,15,20-tri(permethyl-ß-CD)-modified Zn(II)-porphyrin (1; ß-CD = ß-cyclodextrin), was synthesized by means of the click reaction of an alkylated Zn-porphyrin derivative with 6-deoxy-6-azidopermethyl-ß-CD. The complexation between 1 and tetrasodium tetraphenylporphyrintetrasulfonate (5) with different molar ratios led to the formation of two distinctly different nanoarchitectures, which were proven to be vesicle and network aggregates, respectively, by using dynamic light scattering, scanning electron microscopy, transmission electron microscopy, and atomic force microscopy. On the basis of the results of the time-dependent TEM studies, fluorescence, and NMR spectroscopic measurements, we have determined that the mechanism of the morphology transition from vesicles to networks is controlled by the stepwise complexation of 1 with 5. Furthermore, these supramolecular nanoarchitectures show the controlled- release property of doxorubicin as potential candidates for drug delivery.