Controlled release of hydrophilic guest molecules from photoresponsive nucleolipid vesicles

Amphiphilic hybrid nucleolipids bear the structural and functional hallmarks of both lipids and nucleic acids and hold great potential for biotechnological applications. However, further tailoring of their structures and properties for specific applications represents a major challenge. We here report a novel design and synthesis of a light-responsive nucleolipid by introducing an o-nitrobenzyl group that acts as a linker between a nucleotide and a lipid. The nucleolipid was applied readily to preparing smart vesicles and encapsulating hydrophilic guest molecules 5(6)-carboxyfluorescein (CF) in their inner aqueous phase. Upon light irradiation, their vesicular structure was disrupted as a result of the photolytic degradation of the nucleotide, resulting in CF release. Furthermore, temporally controlled CF release from these vesicles could be readily realized by turning on and off light. By demonstrating the molecular assembly and photodisassembly cycle, this report aims to stimulate further research exploring practical applications of nucleolipids. © 2013 American Chemical Society.