Tetrazole Photoclick Chemistry: Reinvestigating Its Suitability as a Bioorthogonal Reaction and Potential Applications |
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| Authors: | Dr. Zhengqiu Li Linghui Qian Prof. Dr. Lin Li Dr. Jan C. Bernhammer Prof. Dr. Han Vinh Huynh Prof. Dr. Jun‐Seok Lee Prof. Dr. Shao Q. Yao |
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| Affiliation: | 1. Department of Chemistry, National University of Singapore, Singapore, Singapore;2. College of Pharmacy, Jinan University, Guangzhou, China;3. Key Laboratory of Flexible Electronics & Institute of Advanced Materials, Nanjing Tech University, Nanjing, China;4. Molecular Recognition Research Center, Korea Institute of Science and Technology, Department of Biological Chemistry, University of Science & Technology, Republic of Korea |
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| 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. |
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| Keywords: | affinity-based probes bioorthogonality imaging photo-crosslinking tetrazoles |
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