Wei Chao, Wang Xiaofen, Li Xueyan, Jia Xu, Hao Xinya, Zhang Jiangyan, Zhang Pingzhu, Li Xiaoliu
Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of Ministry of Education, Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Environmental Science, Hebei University, Baoding 071002, China; College of Chemistry and Environmental Science, Hebei University, Baoding 071002, China.
Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of Ministry of Education, Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Environmental Science, Hebei University, Baoding 071002, China; College of Chemistry and Environmental Science, Hebei University, Baoding 071002, China.
Spectrochim Acta A Mol Biomol Spectrosc. 2020 Feb 15;227:117765. doi: 10.1016/j.saa.2019.117765. Epub 2019 Nov 6.
Nitroxyl (HNO) plays an important role in multiple physiological and pathological processes, but the detailed generation mechanism of the endogenous HNO still remained to explore and perfect further. There is an urgent need to develop an excellent fluorescent probe for selective recognition and sensitive detection of HNO in biological systems. Near-infrared (NIR) fluorescent probes with a large Stokes shift are an ideal tool for bioimaging applications. Here, we have developed a NIR fluorescent probe with a large Stokes shift, namely, NIR-HNO, to monitor HNO in cells and zebrafish. NIR-HNO consists of an isophorone-fused NIR fluorescence reporter and a diphenylphosphinobenzoyl HNO-responsive unit. Based on an aza-ylide intramolecular ester aminolysis reaction, NIR-HNO showed a rapid selective NIR fluorescent turn-on response for HNO, high sensitivity (detection limit was 39.6 nM), and large Stokes shift (265 nm). The biological imaging results indicate that NIR-HNO is a good candidate for imaging of endogenous HNO in living systems.
硝酰（HNO）在多种生理和病理过程中发挥着重要作用，但内源性HNO的详细生成机制仍有待进一步探索和完善。迫切需要开发一种出色的荧光探针，用于在生物系统中选择性识别和灵敏检测HNO。具有大斯托克斯位移的近红外（NIR）荧光探针是生物成像应用的理想工具。在此，我们开发了一种具有大斯托克斯位移的NIR荧光探针，即NIR-HNO，用于监测细胞和斑马鱼中的HNO。NIR-HNO由异佛尔酮稠合的NIR荧光报告基团和二苯基膦酰苯甲酰基HNO响应单元组成。基于氮杂叶立德分子内酯氨解反应，NIR-HNO对HNO表现出快速的选择性NIR荧光开启响应、高灵敏度（检测限为39.6 nM）和大斯托克斯位移（265 nm）。生物成像结果表明，NIR-HNO是用于活系统中内源性HNO成像的良好候选物。
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