Tian Xinwei, Li Zhao, Pang Yaxing, Li Dongyu, Yang Xingbin
Shaanxi Engineering Laboratory for Food Green Processing and Safety Control, College of Food Engineering and Nutritional Science, Shaanxi Normal University , Xi'an, Shaanxi 710062, People's Republic of China.
J Agric Food Chem. 2017 Nov 1;65(43):9553-9558. doi: 10.1021/acs.jafc.7b03598. Epub 2017 Oct 20.
A novel near-infrared fluorescence off-on probe, (E)-3,3-dimethyl-1-propyl-2-(2-(6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyloxy)-2,3-dihydro-1H-xanthen-4-yl)vinyl)-3H-indolium (1), is developed and applied to benzoyl peroxide (BPO) detection in real samples and fluorescence imaging in living cells and zebrafish. When arylboronate as the recognition unit is connected to a stable hemicyanine skeleton, the probe is readily prepared, which exhibits superior analytical performance, such as near-infrared fluorescence emission over 700 nm and high sensitivity with a low detection limit of 47 nM. Upon reaction with BPO, phenylboronic acid pinacol ester is oxidized, followed by hydrolysis and 1,4-elimination of o-quinone methide to release fluorophore. In addtion, the probe displays high selectivity toward BPO over other common substances, which makes it of great potential use in quantitative and simple detection of BPO in wheat flour and antimicrobial agent. More importantly, the probe has been successfully demonstrated for monitoring BPO in living HeLa cells and zebrafish. The probe with superior properties could be of great potential use in other biosystems and in vivo studies.
一种新型近红外荧光开关探针，（E）-3,3-二甲基-1-丙基-2-（2-（6-（2-（4,4,5,5-四甲基-1,3,2-二氧杂硼烷-2-基）苄氧基）-2,3-二氢-1H-呫吨-4-基）乙烯基）-3H-吲哚鎓（1）被开发出来，并应用于实际样品中过氧化苯甲酰（BPO）的检测以及活细胞和斑马鱼的荧光成像。当作为识别单元的芳基硼酸酯连接到稳定的半菁骨架上时，该探针易于制备，具有优异的分析性能，如700nm以上的近红外荧光发射以及低至47 nM的高灵敏度检测限。与BPO反应时，苯硼酸频哪醇酯被氧化，随后水解并发生邻醌甲基化物的1,4-消除反应以释放荧光团。此外，该探针对BPO相对于其他常见物质具有高选择性，这使其在面粉中BPO的定量和简单检测以及抗菌剂方面具有巨大的潜在应用价值。更重要的是，该探针已成功用于监测活的HeLa细胞和斑马鱼中的BPO。具有优异性能的该探针在其他生物系统和体内研究中可能具有巨大的潜在应用价值。
