A chiral supramolecular hydrogel (CSH) is designed for selective loading of chiral drugs and pH-responsive drug delivery. A derivative of phenylalanine is first synthesized as the gelator, which can be self-assembled to the CSH via intermolecular hydrogen bonding. The resultant CSH is composed of spiral nanofibers and exhibits reversible phase transition behavior (sol–gel) depending on heating/cooling process and pH values. More importantly, the CSH can be used for the selective loading of chiral drug naproxen (NPX) due to the stronger attractive interactions between CSH and S-NPX resulted from their same optical activity. Interestingly, the delivery of S-NPX from the CSH is pH-sensitive and the cumulative release of S-NPX is significantly enhanced in alkaline solutions (pH = 10.0), which might be ascribed to the broken hydrogen bonding and the consequently ruined nanostructure of the CSH under alkaline conditions.
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