Department of Chemistry and Biochemistry, University of Arizona, Building 41, Room 104, 1306 East University Boulevard, Tucson, Arizona 85721, United States.
Bioconjug Chem. 2021 Nov 17;32(11):2432-2438. doi: 10.1021/acs.bioconjchem.1c00459. Epub 2021 Nov 3.
This work describes the development of phenyl diazenyl piperidine triazene derivatives that can be activated to release aryl diazonium ions for labeling of proteins using light. These probes show marked bench stability at room temperature and can be photoisomerized via low-intensity UVA irradiation at physiological pH. Upon isomerization, the triazenes are rendered more basic and readily protonate to release reactive aryl diazonium ions. It was discovered that the intensity and duration of the UV light was essential to the observed diazonium ion reactivity in competition with the traditionally observed photolytic radical pathways. The combination of their synthetic efficiency coupled with their overall stability makes triazenes an attractive candidate for use in bioconjugation applications. Bioorthogonal handles on the triazenes are used to demonstrate the ease by which proteins can be modified.
这项工作描述了苯基亚氨基哌啶三氮烯衍生物的开发，这些衍生物可以被激活，以释放芳基重氮离子，用于使用光标记蛋白质。这些探针在室温下表现出显著的稳定性，并可以在生理 pH 值下通过低强度的 UVA 照射进行光异构化。异构化后，三氮烯变得更碱性，容易质子化以释放反应性芳基重氮离子。研究发现，UV 光的强度和持续时间对于观察到的重氮离子反应性至关重要，与传统观察到的光解自由基途径竞争。三氮烯的合成效率与其整体稳定性的结合使其成为生物偶联应用的有吸引力的候选物。三氮烯上的生物正交接头用于证明修饰蛋白质的容易程度。
