Issue 14, 2023

A mannose-functionalized pillar[5]arene-based supramolecular fluorescent probe for real-time monitoring of gemcitabine delivery to cancer cells

Abstract

The construction of a 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 the host molecule mannose-functionalized pillar[5]arene (ManP5) and a guest molecule (G) that is a near-infrared fluorescence receptor (dicyanomethylene-4H-pyran, DCM) derivative. ManP5⊃G self-assembles into nano-vesicles loaded with nonfluorescent anticancer drugs GEM to produce GEM@ManP5⊃G nanoparticles (NPs). The study results showed that GEM@ManP5⊃G NPs have good GSH responsiveness, achieving 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 the real-time monitoring of GEM release. In addition, the GEM@ManP5⊃G NPs could effectively reduce the side effects of GEM on normal cells while improving the cancer cell damage capability. Therefore, the nanodrug delivery system constructed using the pillar[5]arene-based supramolecular fluorescent probe exhibits excellent capabilities of targeted drug delivery and the real-time monitoring of nonfluorescent drug release, which provides a novel approach to improve the efficacy of nonfluorescent drugs in enhancing chemotherapy.

Graphical abstract: A mannose-functionalized pillar[5]arene-based supramolecular fluorescent probe for real-time monitoring of gemcitabine delivery to cancer cells

Supplementary files

Article information

Article type
Research Article
Submitted
31 mar 2023
Accepted
05 iyn 2023
First published
06 iyn 2023

Org. Chem. Front., 2023,10, 3491-3497

A mannose-functionalized pillar[5]arene-based supramolecular fluorescent probe for real-time monitoring of gemcitabine delivery to cancer cells

S. Chao, P. Huang, Z. Shen, Y. Pei, Y. Lv, Y. Lu and Z. Pei, Org. Chem. Front., 2023, 10, 3491 DOI: 10.1039/D3QO00476G

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