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BODIPY-Based Fluorescent Probe for Dual-Channel Detection of Nitric Oxide and Glutathione: Visualization of Cross-Talk in Living Cells

Chen, Xiao-Xiao, Niu, Li-Ya, Shao, Na, Yang, Qing-Zheng
Analytical chemistry 2019 v.91 no.7 pp. 4301-4306
arginine, fluorescence, fluorescent dyes, glutathione, interferon-gamma, lipopolysaccharides, macrophages, nitric oxide, triazoles
Nitric oxide (NO) and glutathione (GSH) have interplaying roles in oxidant-antioxidant balance. In this work, we developed the first example of a single fluorescent probe that displayed a turn-on fluorescence response toward NO and GSH from dual emission channels. The probe was synthesized by introducing 4-amino-3-(methylamino)-phenol to a BODIPY scaffold. Specifically, the NO-mediated transformation of diamine into a triazole triggered the fluorescence in the green channel, and the GSH-induced SNAr substitution reaction led to the red-shifted emission in the red channel. The probe was successfully applied to detect the exogenous and endogenous NO and GSH in macrophage cells. More importantly, the probe revealed that NO induced by interferon-γ (IFN-γ), lipopolysaccharide (LPS), and l-arginine (l-Arg) could also elicit the augmentation of intracellular GSH. We anticipate the probe would hold great potential for investigating the redox balance in biological processes.