Tianjin Key Laboratory for Photoelectric Materials and Devices, School of Materials Science & Engineering, Tianjin University of Technology, Tianjin 300384, China.
Key Laboratory of Display Materials and Photoelectric Devices, Ministry of Education, School of Materials Science & Engineering, Tianjin University of Technology, Tianjin, 300384, China.
Org Biomol Chem. 2024 Aug 28;22(34):6981-6987. doi: 10.1039/d4ob01195c.
Glyoxal (GL) is a reactive α-dicarbonyl compound generated from glycated proteins in the Maillard reaction. It has attracted particular attention over the past few years because of its possible clinical significance in chronic and age-related diseases. In this work, a reaction-based red emission fluorescent probe GL1 has been synthesized successfully by grafting an alkyl group onto an amino group to regulate its selectivity for GL. Under physiological conditions, the fluorescence intensity of GL1 at 640 nm obviously increased with the increase of GL concentration, and it exhibited high selectivity for GL over other reactive carbonyl compounds, as well as a lower detection limit (0.021 μM) and a larger Stokes shift (112 nm). At the same time, GL1 can selectively accumulate in mitochondria and can be used to detect exogenous and endogenous GL in living cells with low cytotoxicity.
乙二醛（GL）是美拉德反应中糖化蛋白质产生的一种反应性α-二羰基化合物。近年来，由于其在慢性和与年龄相关的疾病中的可能临床意义，引起了特别关注。在这项工作中，通过在氨基上嫁接烷基基团成功合成了基于反应的红色发射荧光探针 GL1，以调节其对 GL 的选择性。在生理条件下，GL1 在 640nm 处的荧光强度随着 GL 浓度的增加而明显增加，并且对 GL 具有高选择性，对其他反应性羰基化合物也具有较低的检测限（0.021μM）和较大的斯托克斯位移（112nm）。同时，GL1 可以选择性地积累在线粒体中，并可以用于检测活细胞中外源和内源性 GL，具有低细胞毒性。
