Abstract
The bioorthogonality of tetrazole photoclick chemistry has been reassessed. Upon photolysis of a tetrazole, the highly reactive nitrile imine formed undergoes rapid nucleophilic reaction with a variety of nucleophiles present in a biological system, along with the expected cycloaddition with alkenes. The alternative use of the tetrazole photoclick reaction was thus explored: tetrazoles were incorporated into Bodipy and Acedan dyes, providing novel photo-crosslinkers with one- and two-photon fluorescence Turn-ON properties that may be developed into protein-detecting biosensors. Further introduction of these photo-activatable, fluorogenic moieties into staurosporine resulted in the corresponding probes capable of photoinduced, no-wash imaging of endogenous kinase activities in live mammalian cells.
Original language | English |
---|---|
Pages (from-to) | 2002-2006 |
Number of pages | 5 |
Journal | Angewandte Chemie - International Edition |
Volume | 55 |
Issue number | 6 |
DOIs | |
Publication status | Published - 2016 Feb 5 |
Externally published | Yes |
Keywords
- affinity-based probes
- bioorthogonality
- imaging
- photo-crosslinking
- tetrazoles
ASJC Scopus subject areas
- Catalysis
- Chemistry(all)