Sheng Yumiao, Xu Kedian, Wang Zhenzhen, Gao Yunling
State Key Laboratory Breeding Base of Green Chemistry Synthesis Technology, College of Chemical Engineering, Zhejiang University of Technology, Hangzhou, 310032, China.
Photochem Photobiol Sci. 2025 Jan;24(1):65-77. doi: 10.1007/s43630-024-00672-w. Epub 2024 Dec 20.
A new ratiometric and colorimetric fluorescent probe HTD was synthesized based on the reaction of 4-aminophenyl boronic acid pinacol ester and 4-(3-formyl-4-hydroxyphenyl) benzonitrile. The probe exhibited a unique fluorescence response to hypochlorous acid and had good anti-interference performance in the presence of other interference. When HTD met the NaClO, the light orange fluorescence was changed to green with the blue-shifted emission wavelength from 550 to 500 nm. Moreover, the absorbance of HTD's UV-vis at 300 nm and 375 nm decreased in the presence of NaClO. The limit of detection was 1.83 × 10 M and 2.96 × 10 M based on the fluorescence and UV-vis titration data. NMR, HRMS, and IR spectra suggested that the possible sensing mechanism of HTD to NaClO was the formation of initial compound 4-(3-formyl-4-hydroxyphenyl) benzonitrile due to the oxidation of hypochlorous acid in aqueous solution. The portable test strips were obtained, and the real water sample test reached good results with spiking recoveries among 92.00% ~ 103.25%. Finally, endogenous hypochlorous acid produced by LPS and PMA was successfully detected by HTD in living mice using in situ fluorescence bioimaging.
基于4-氨基苯基硼酸频哪醇酯与4-(3-甲酰基-4-羟基苯基)苯甲腈的反应，合成了一种新型的比率型和比色荧光探针HTD。该探针对次氯酸表现出独特的荧光响应，在存在其他干扰的情况下具有良好的抗干扰性能。当HTD与NaClO相遇时，浅橙色荧光变为绿色，发射波长从550 nm蓝移至500 nm。此外，在NaClO存在下，HTD在300 nm和375 nm处的紫外可见吸收度降低。基于荧光和紫外可见滴定数据，检测限分别为1.83×10⁻⁶ M和2.96×10⁻⁶ M。核磁共振、高分辨质谱和红外光谱表明，HTD对NaClO的可能传感机制是由于水溶液中次氯酸的氧化作用形成了初始化合物4-(3-甲酰基-4-羟基苯基)苯甲腈。制备了便携式测试条，对实际水样进行测试，加标回收率在92.00%~103.25%之间，取得了良好的结果。最后，利用原位荧光生物成像技术，HTD成功检测了活体小鼠中由脂多糖和佛波酯产生的内源性次氯酸。
