Ding Ning, Li Zhao, Hao Yitong, Zhang Chengxiao
Shaanxi Engineering Laboratory for Food Green Processing and Safety Control, and Shaanxi Key Laboratory for Hazard Factors Assessment in Processing and Storage of Agricultural Products, College of Food Engineering and Nutritional Science, Shaanxi Normal University, Xi'an 710062, China.
Key Laboratory of Analytical Chemistry for Life Science of Shaanxi Province, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an 710062, China.
Anal Chem. 2022 Sep 6;94(35):12120-12126. doi: 10.1021/acs.analchem.2c02166. Epub 2022 Aug 25.
Formaldehyde (FA), the smallest molecular aldehyde with strong reducing properties, could regulate body homeostasis endogenously during physiological and pathological processes. The effective near-infrared (NIR) fluorescent probe is needed as a visualizer of FA in biologic organisms. In this work, a novel NIR fluorescent - was designed on the basis of - introducing a strong nucleophilic hydrazine group, which can be used as a quenching and recognizing moiety for the detection of FA. With the treatment of FA, the hydrazine group of - undergoes condensation and achieves a turn-on NIR fluorescence signal at a wavelength of 706 nm. The spectroscopic performance of for FA was evaluated, and it exhibited high sensitivity and selectivity for the detection of FA in solution. Moreover, compared to the amine moiety-based - which our group reported, we found that hydrazine moiety-based -, exhibited a better reaction time of within 10 min and a lower detection limit of 0.68 μM, reflecting that the reaction of FA with hydrazine moiety is faster and more sensitive than that of FA with the amino group. More importantly, - was successfully applied to real-time imaging of endogenous FA by reacting with effective stimulant tetrahydrofolate and scavenger sodium bisulfite in zebrafish and mice. It is expected that we can provide a new rapid, sensitive NIR fluorescence theoretical basis for FA detection and in vivo imaging applications.
甲醛（FA）是具有强还原性质的最小分子醛，在生理和病理过程中可内源性调节机体稳态。在生物体内需要有效的近红外（NIR）荧光探针作为FA的可视化工具。在这项工作中，基于引入强亲核肼基设计了一种新型近红外荧光探针，该肼基可作为检测FA的猝灭和识别部分。用FA处理后，该探针的肼基发生缩合反应，在706nm波长处实现近红外荧光信号的开启。评估了该探针检测FA的光谱性能，其对溶液中FA的检测表现出高灵敏度和选择性。此外，与本课题组报道的基于胺基的探针相比，我们发现基于肼基的探针反应时间更短，在10分钟内即可完成反应，检测限更低，为0.68μM，这表明FA与肼基的反应比FA与氨基的反应更快、更灵敏。更重要的是，该探针通过与斑马鱼和小鼠体内有效的刺激物四氢叶酸和清除剂亚硫酸氢钠反应，成功应用于内源性FA的实时成像。预计可为FA检测和体内成像应用提供一种新的快速、灵敏的近红外荧光理论基础。
