School of Chemical Science and Technology, Ynunan University, 650500, Kunming, P. R. China.
Chem Asian J. 2022 Sep 1;17(17):e202200634. doi: 10.1002/asia.202200634. Epub 2022 Jul 19.
Aryl azide and diaryl tetrazole are both photoactive molecules, which can form nitrene and nitrile imine intermediates respectively by photolysis. Depending on the new finding that the azide can suppress the photolysis of tetrazole in the azide-tetrazole conjugated system, we developed aryl azide-tetrazole probes for the photoactivatable fluorogenic azide alkyne click (PFAAC) reaction, in which the aryl azide-tetrazole probes were not phoroactivatable fluorogenic itself, but the triazole products after click reaction were prefluorophore that can be activated by light. Therefore, in PFAAC chemistry, the fluorescent probes can be activated by two orthogonal events: azide-alkyne click reaction and light, which leads to spatiotemporal resolution and high signal-to-noise ratio. This PFAAC process was proved in vitro by copper-catalyzed or strain-promoted azide-alkyne reactions and in live cells by spatiotemporally controlled organelle imaging. By incorporation a linker to the azide-tetrazole conjugate, this PFAAC chemistry could covalently label extra probes to the biomolecules and spatiotemporally detecting this process by photoinduced fluorescence.
芳基叠氮化物和二芳基四唑都是光活性分子，分别可以通过光解形成氮宾和腈亚胺中间体。根据叠氮化物可以抑制叠氮化物-四唑共轭体系中四唑光解的新发现，我们开发了芳基叠氮化物-四唑探针用于光活化荧光叠氮炔点击（PFAAC）反应，其中芳基叠氮化物-四唑探针本身不是光致荧光的，但点击反应后的三唑产物是可以被光激活的预荧光团。因此，在 PFAAC 化学中，荧光探针可以通过两个正交事件激活：叠氮化物-炔点击反应和光，从而实现时空分辨率和高信噪比。该 PFAAC 过程通过铜催化或应变促进的叠氮化物-炔反应在体外得到证实，并通过时空控制的细胞器成像在活细胞中得到证实。通过将一个连接子与叠氮化物-四唑缀合物结合，该 PFAAC 化学可以将额外的探针共价标记到生物分子上，并通过光诱导荧光对该过程进行时空检测。
