The application of mitochondrial targetable pyronine-pyridinium skeleton in the detection of nitroreductase
Abstract In this paper, a new compound ( 3 ) with pyronine-pyridine skeleton had a strong fluorescence at pH 5.0−9.0, while the emission turned off at pH = 1.0–2.0. It was a mitochondrial biomarker in cancer cells (KB, 4T1, HeLa) and normal cells (Ges-1, L929, WS1). Based on these above results, probe 1 with pyronine-pyridinium skeleton was further designed and prepared to detect nitroreductase (NTR). The nitrofuran group of probe 1 was reduced and eliminated upon addition of NTR and nicotinamide adenine dinucleotide (NADH) to produce compound 3 , and the d-PET process could be allowed in the pyronine-pyridinium structure of probe 1 but it was prohibited in the pyronine-pyridine skeleton of compound 3 after detection, hence probe 1 showed a nearly turn-on signal in red light region at 565–800 nm with emission maxima at 604 nm. The detection limit was calculated as low as 2.2 ng/mL. Furthermore, fluorescence imaging experiments with live HeLa and Ges-1 cells were performed, and probe 1 could serve as a mitochondrial targetable probe to detect nitroreductase in red channel. Highlights The rosamine (3) with pyronine−pyridine structure was designed, and it was a red emission mitochondrial targetable probe. Pyridinium salt based compound (1) was served as a mitochondrial targetable NTR probe; it has a low detection limit (2.2 ng/mL). Nearly OFF-ON response, red emission. Graphical abstract [DISPLAY OMISSION]
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