The construction of multifunctional nanodrug delivery system for the targeted delivery and real-time monitoring of nonfluorescent drugs has become one of the most important topics in cancer therapy. Herein, a novel supramolecular fluorescent probe (ManP5⊃G) for real-time monitoring of nonfluorescent drug gemcitabine (GEM) delivery to the cancer cells was constructed based on the host-guest interactions between host molecule mannose-functionalized pillar[5]arene (ManP5) and a guest molecule (G) which is a near-infrared fluorescence receptor (Dicyanomethylene-4H-pyran, DCM) derivative. ManP5⊃G could self-assemble into nano-vesicles loaded with nonfluorescent anticancer drugs GEM to obtain GEM@ManP5⊃G NPs. The study results showed that GEM@ManP5⊃G NPs have good GSH responsiveness, which could achieve efficient delivery of GEM to cancer cells by mannose recognizing MCF-7 cells and selective release under GSH stimulation. Meanwhile, the fluorescence recovery of DCM stimulated by GSH can realize real-time monitoring of GEM release. In addition, GEM@ManP5⊃G NPs could effectively reduce the side effects of GEM on normal cells while improving the cancer cells damage capability. Therefore, the nanodrug delivery system constructed by pillar[5]arene-based supramolecular fluorescent probe exhibits excellent capabilities of targeting drug delivery and real-time monitoring of nonfluorescent drugs release, which provides a novel approach to improve the efficacy of nonfluorescent drugs in enhancing chemotherapy.

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