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Conferring Phosphorogenic Properties on Iridium(III)‐Based Bioorthogonal Probes through Modification with a Nitrone Unit
Author(s) -
Lee Lawrence ChoCheung,
Lau Jonathan ChunWai,
Liu HuaWei,
Lo Kenneth KamWing
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201509396
Subject(s) - bioorthogonal chemistry , nitrone , chemistry , combinatorial chemistry , moiety , iridium , ligand (biochemistry) , cycloaddition , reagent , click chemistry , stereochemistry , biochemistry , organic chemistry , catalysis , receptor
The use of bioorthogonal probes that display fluorogenic or phosphorogenic properties is advantageous to the labeling and imaging of biomolecules in live cells and organisms. Herein we present the design of three iridium(III) complexes containing a nitrone moiety as novel phosphorogenic bioorthogonal probes. These probes were non‐emissive owing to isomerization of the C=N group but showed significant emission enhancement upon cycloaddition reaction with strained cyclooctynes. Interestingly, the connection of the nitrone ligand to the cationic iridium(III) center led to accelerated reaction kinetics. These nitrone complexes were also identified as phosphorogenic bioorthogonal labels and imaging reagents for cyclooctyne‐modified proteins. These findings contribute to the development of phosphorogenic bioorthogonal probes and imaging reagents.