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Live‐Cell Imaging of Cyclopropene Tags with Fluorogenic Tetrazine Cycloadditions
Author(s) -
Yang Jun,
Šečkutė Jolita,
Cole Christian M.,
Devaraj Neal K.
Publication year - 2012
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.201202122
Subject(s) - tetrazine , bioorthogonal chemistry , cyclopropene , bioconjugation , chemistry , aqueous medium , cycloaddition , combinatorial chemistry , nanotechnology , computational biology , biochemistry , click chemistry , aqueous solution , biology , organic chemistry , materials science , catalysis
Spotlight on lipids : One of the major limitations of tetrazine bioorthogonal cycloadditions is the requirement of bulky dienophile reaction partners. Methylcyclopropene tags were designed capable of reacting rapidly with tetrazines while maintaining stability in aqueous solution. The suitability of these probes for bioconjugation is shown by imaging cyclopropene‐modified phospholipids in live human cancer cells (see picture).