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- Title
Photoactivatable Fluorogenic Azide‐Alkyne Click Reaction: A Dual‐Activation Fluorescent Probe.
- Authors
Xiao, Mingjun; Zhang, Yi‐Kang; Li, Ranran; Li, Shengtao; Wang, Di; An, Peng
- Abstract
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.
- Subjects
FLUORESCENT probes; RING formation (Chemistry); CONJUGATED systems; SIGNAL-to-noise ratio; TRIAZOLES; BIOMOLECULES
- Publication
Chemistry - An Asian Journal, 2022, Vol 17, Issue 17, p1
- ISSN
1861-4728
- Publication type
Article
- DOI
10.1002/asia.202200634