Near-Infrared Fluorescent Probe for H2S Detection: Will pH Affect the Intracellular Sensing?
- Xiaowen Guan
Xiaowen GuanKey Laboratory of Radiopharmaceuticals, Ministry of Education, College of Chemistry, Beijing Normal University, Beijing 100875, ChinaMore by Xiaowen Guan
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- Hua Lu
Hua LuBeijing Products Quality Supervision and Inspection Institute, Beijing 101300, ChinaMore by Hua Lu
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- Xiyang Ge
Xiyang GeKey Laboratory of Radiopharmaceuticals, Ministry of Education, College of Chemistry, Beijing Normal University, Beijing 100875, ChinaMore by Xiyang Ge
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- Yiyan Yin
Yiyan YinKey Laboratory of Radiopharmaceuticals, Ministry of Education, College of Chemistry, Beijing Normal University, Beijing 100875, ChinaMore by Yiyan Yin
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- Jin Ouyang
Jin OuyangKey Laboratory of Radiopharmaceuticals, Ministry of Education, College of Chemistry, Beijing Normal University, Beijing 100875, ChinaMore by Jin Ouyang
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- Na Na*
Na Na*Email: [email protected]Key Laboratory of Radiopharmaceuticals, Ministry of Education, College of Chemistry, Beijing Normal University, Beijing 100875, ChinaMore by Na Na
Abstract
Near-infrared (NIR) fluorescent probe has exhibited unique advantages for in vitro and in vivo detection of hydrogen sulfide (H2S), an important endogenous gasotransmitter in redox homeostasis and multiple life processes. However, both the pH-dependent emission of NIR probes and H2S conversions would normally affect the accurate detection in cellular environments in different acidic conditions. Herein, both experiments and theoretical calculations were carried out to examine the effect of pH on intracellular sensing of H2S by the NIR probe. Selecting a NIR probe of R1 with dual-excited NIR responses to H2S as the model, the pH-dependent R1 emission was confirmed by optical measurements, whose structural changes were further examined by mass spectrometry (MS). Significantly, the dynamic changes versus pH increase were employed for the online monitoring of ambient MS (AMS), observing important intermediate species without sample pretreatments. Thereby, intermediates and transition states were confirmed by theoretical calculations, which proposed the mechanism of nucleophilic substitution, followed by the hydrolysis process with increasing pH. As examined, R1 exhibited a relatively stable NIR emission at pH 4–8, while a dramatic change in signals occurred at higher-pH conditions. Therefore, R1 was demonstrated to be reliable for intracellular sensing of H2S and had been confirmed by cell imaging. This work has initiated a comprehensive strategy for evaluating fluorescence (FL) probes, showing potential for the development of fluorescent probes.
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