title: Tetrazole Photoclick Chemistry: Reinvestigating Its Suitability as a Bioorthogonal Reaction and Potential Applications.
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.
authors.affiliation: Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore, 117543, Singapore.|College of Pharmacy, Jinan University, Guangzhou, 510632, China.
authors.forename: Zhengqiu
authors.initials: Z
authors.lastname: Li
authors.affiliation: Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore, 117543, Singapore.
authors.forename: Linghui
authors.initials: L
authors.lastname: Qian
authors.affiliation: Key Laboratory of Flexible Electronics & Institute of Advanced Materials, Nanjing Tech University, Nanjing, 211816, China.
authors.forename: Lin
authors.initials: L
authors.lastname: Li
authors.affiliation: Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore, 117543, Singapore.
authors.forename: Jan C
authors.initials: JC
authors.lastname: Bernhammer
authors.affiliation: Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore, 117543, Singapore.
authors.forename: Han Vinh
authors.initials: HV
authors.lastname: Huynh
authors.affiliation: Molecular Recognition Research Center, Korea Institute of Science and Technology, Department of Biological Chemistry, University of Science & Technology, Republic of Korea.
authors.forename: Jun-Seok
authors.initials: JS
authors.lastname: Lee
authors.affiliation: Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore, 117543, Singapore. chmyaosq@nus.edu.sg.
authors.forename: Shao Q
authors.initials: SQ
authors.lastname: Yao
mesh_terms: D015374:Biosensing Techniques; D057930:Click Chemistry; D005453:Fluorescence; D005456:Fluorescent Dyes / Q000737:chemistry; D056945:Hep G2 Cells; D006801:Humans; D015394:Molecular Structure; D055668:Photochemical Processes; D011494:Protein Kinases / Q000032:analysis* / Q000378:metabolism; D013777:Tetrazoles / Q000737:chemistry*
chemical_list: D005456:Fluorescent Dyes; D013777:Tetrazoles; C045574:1H-tetrazole; D011494:Protein Kinases
keywords: affinity-based probes; bioorthogonality; imaging; photo-crosslinking; tetrazoles