Fullerene-based amino acid ester chlorides self-assembled as spherical nano-vesicles for drug delayed release

Abstract

Fullerenes with novel structures find numerous potential applications, particularly in the fields of biology and pharmaceutics. Among various fullerene derivatives, those exhibiting amphiphilic character and capable of self-assembly into vesicles are particularly interesting, being suitable for delayed drug release. Herein, we report the synthesis and self-assembly of biocompatible hollow nanovesicles with bilayer shells from amphiphilic functionalized fullerenes C60R5Cl (R=methyl ester of 4-aminobutyric/glutamic acid or phenylalanine). The thus prepared vesicles exhibit sizes of 80–135nm (depending on R) and can be used as delayed-release carriers of anti-cancer drugs such as 5-fluorouracil, cyclophosphamide, and cisplatin, with the time of 5-fluorouracil release from drug-containing vesicles exceeding that of non-encapsulated forms by a factor of three. We further reveal the effect of R on the loading amount and release rate/amount of vesicle-encapsulated drugs, demonstrating a potential pharmaceutical application of the prepared nanovesicles depending on the nature of R.