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S-nitroso-N-acetylpenicillamine (SNAP) and hydrophobic succinyl pyrene (SuPy) were conjugated to hyaluronic acid (HA) through cystamine dihydrochloride (Cys) linkers to synthesize NO-conjugated reductive–responsive prodrugs HA-Cys-(SNAP/SuPy). The prodrug could self-assemble into spherical micelles with a particle size of &lt;200 nm. In a reductive environment (10 mM dithiothreitol, DTT), a substantial amount of the grafted NO was released, faster than that observed under physiological condition. Flow cytometry revealed that the uptake of HA-targeted DOX-encapsulated micelles was faster than that of free DOX. Microscopic analysis showed that NO-conjugated HA-Cys-(SNAP/SuPy) effectively generated NO within the cells and promoted the anticancer effect of DOX.

Reductive responsive hyaluronic acid conjugated S-nitrothiol prodrugs as drug carriers