Tetrazole photoclick chemistry: Reinvestigating its suitability as a bioorthogonal reaction and potential applications

Zhengqiu Li, Linghui Qian, Lin Li, Jan C. Bernhammer, Han Vinh Huynh, Jun Seok Lee, Shao Q. Yao

Research output: Contribution to journalArticlepeer-review

122 Citations (Scopus)

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 languageEnglish
Pages (from-to)2002-2006
Number of pages5
JournalAngewandte Chemie - International Edition
Volume55
Issue number6
DOIs
Publication statusPublished - 2016 Feb 5
Externally publishedYes

Keywords

  • affinity-based probes
  • bioorthogonality
  • imaging
  • photo-crosslinking
  • tetrazoles

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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