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Fast and Sensitive Pretargeted Labeling of Cancer Cells through a Tetrazine/ trans ‐Cyclooctene Cycloaddition
Author(s) -
Devaraj Neal K.,
Upadhyay Rabi,
Haun Jered B.,
Hilderbrand Scott A.,
Weissleder Ralph
Publication year - 2009
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.200903233
Subject(s) - tetrazine , bioorthogonal chemistry , cyclooctene , chemistry , cycloaddition , fluorescence , derivative (finance) , antibody , combinatorial chemistry , biochemistry , click chemistry , biology , immunology , catalysis , organic chemistry , physics , quantum mechanics , financial economics , economics
A label for six, please! A fluorescent tetrazine derivative was used to image trans ‐cyclooctene‐modified affinity ligands on live cancer cells through a bioorthogonal cycloaddition with a reaction rate of approximately 6000±200 M −1 s −1 in serum at 37 °C (see scheme). To maximize the fluorescence signal, up to six trans ‐cyclooctene moieties were attached to the antibody used to pretarget cells for labeling.