Rosamine with pyronine-pyridinium skeleton: unique mitochondrial targetable structure for fluorescent probes.
Ling YangJin-Yun NiuRu SunYu-Jie XuJian-Feng GePublished in: The Analyst (2018)
Two rosamine-based probes (1a-b) with pyronine-pyridinium skeleton were designed and prepared. Probe 1a bearing boron ester unit was oxidized and eliminated upon addition of hydrogen peroxide (H2O2), and the emission spectrum exhibited OFF-ON response accompanied by 33-fold fluorescent enhancement. In contrast, the fluorescence intensity of probe 1b enhanced 58 times after the dinitrophenyl ether part within the probe was removed by nucleophilic substitution with hydrosulfide (H2S). The design concept was based on the d-PET process in pyronine-pyridinium structures, and free 4-pyridinyl-substituted pyronine dye showing strong fluorescence was released followed by elimination. Furthermore, as biocompatible molecules, probes 1a-b have been successfully applied for imaging in live HeLa and Ges-1 cells, and all of them can serve as mitochondrial targetable probes in red channel for detecting independent species.
Keyphrases
- living cells
- single molecule
- hydrogen peroxide
- fluorescent probe
- oxidative stress
- high resolution
- induced apoptosis
- cell cycle arrest
- quantum dots
- nitric oxide
- magnetic resonance
- ionic liquid
- computed tomography
- high intensity
- molecular docking
- positron emission tomography
- cell proliferation
- mass spectrometry
- endoplasmic reticulum stress
- contrast enhanced
- pet imaging
- drug release
- pi k akt
- solid state