The synthesis, fluorogenic characterization, and labeling application of four tetrazine-quenched cyanine probes with emission maxima in the red-far red range is reported. Fluorescence of the cyanine-cores is quenched via through-bond-energy-transfer (TBET) exerted by a bioorthogonal tetrazine unit. Upon bioorthogonal labeling reaction with cyclooctyne tagged proteins, the quenching effect ceases, and thus the fluorescence reinstates, resulting in an increase in fluorescence intensity. As a rare example among indocyanines, one of our new probes was found suitable in STED-based super-resolution imaging. The applicability of this fluorogenic Tet-Cy3 probe was therefore further demonstrated in the bioorthogonal labeling of cytoskeletal protein, actin, with subsequent super-resolution microscopy (STED) imaging even under no-wash conditions.
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| http://dx.doi.org/10.1021/acs.bioconjchem.8b00061 | DOI Listing |
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