Xu Kangshuo, Tang Na, Liu Furong, Ai Yin, Ding Haichang, Fan Congbin, Liu Gang, Pu Shouzhi
Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science and Technology Normal University, Nanchang 330013, PR China.
Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science and Technology Normal University, Nanchang 330013, PR China.
Spectrochim Acta A Mol Biomol Spectrosc. 2024 Sep 5;317:124415. doi: 10.1016/j.saa.2024.124415. Epub 2024 May 6.
SO derivatives play an important role in many metabolic processes, excessive ingestion of them can lead to serious complications of various diseases. In this work, a novel dual ratiometric NIR fluorescent probe XT-CHO based on ICT effect was synthesized for detecting SO derivative. In the design of the probe, the α, β-unsaturated bond formed between benzopyran and coumarin was used as the reaction site for SO, meanwhile, the extended π-conjugate system promoted maximum emission wavelength of the probe up to 708 nm. Notably, the probe exhibited high selectivity and sensitivity for detecting SO, the limit of detection reached 2.13 nM and 58.5 nM in fluorescence spectra and UV-Vis absorption spectra, respectively. The reaction mechanism of SO and XT-CHO had been verified by H NMR, ESI-MS spectra and DFT calculation. Moreover, the probe was successfully applied in detecting endogenous and exogenous SO in living cells and proved possessed the mitochondrial targeted ability.
硫氧衍生物在许多代谢过程中发挥着重要作用，过量摄入会导致各种疾病的严重并发症。在这项工作中，合成了一种基于ICT效应的新型双比率近红外荧光探针XT-CHO用于检测硫氧衍生物。在探针设计中，苯并吡喃与香豆素之间形成的α,β-不饱和键用作硫氧的反应位点，同时，扩展的π共轭体系促使探针的最大发射波长达到708 nm。值得注意的是，该探针对硫氧的检测具有高选择性和灵敏度，在荧光光谱和紫外-可见吸收光谱中的检测限分别达到2.13 nM和58.5 nM。通过核磁共振氢谱、电喷雾电离质谱光谱和密度泛函理论计算验证了硫氧与XT-CHO的反应机理。此外，该探针成功应用于活细胞内源性和外源性硫氧的检测，并证明具有线粒体靶向能力。
