Bioorthogonal labeling with tetrazine-dyes for super-resolution microscopy.

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ID: 80282
2019
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Abstract
Genetic code expansion (GCE) technology allows the specific incorporation of functionalized noncanonical amino acids (ncAAs) into proteins. Here, we investigated the Diels-Alder reaction between trans-cyclooct-2-ene (TCO)-modified ncAAs, and 22 known and novel 1,2,4,5-tetrazine-dye conjugates spanning the entire visible wavelength range. A hallmark of this reaction is its fluorogenicity - the tetrazine moiety can elicit substantial quenching of the dye. We discovered that photoinduced electron transfer (PET) from the excited dye to tetrazine is the main quenching mechanism in red-absorbing oxazine and rhodamine derivatives. Upon reaction with dienophiles quenching interactions are reduced resulting in a considerable increase in fluorescence intensity. Efficient and specific labeling of all tetrazine-dyes investigated permits super-resolution microscopy with high signal-to-noise ratio even at the single-molecule level. The different cell permeability of tetrazine-dyes can be used advantageously for specific intra- and extracellular labeling of proteins and highly sensitive fluorescence imaging experiments in fixed and living cells.
Reference Key
beliu2019bioorthogonalcommunications Use this key to autocite in the manuscript while using SciMatic Manuscript Manager or Thesis Manager
Authors Beliu, Gerti;Kurz, Andreas J;Kuhlemann, Alexander C;Behringer-Pliess, Lisa;Meub, Mara;Wolf, Natalia;Seibel, Jürgen;Shi, Zhen-Dan;Schnermann, Martin;Grimm, Jonathan B;Lavis, Luke D;Doose, Sören;Sauer, Markus;
Journal Communications biology
Year 2019
DOI
10.1038/s42003-019-0518-z
URL
Keywords
photocatalyst l-cysteine polyethylene glycol mn-zns quantum dot organic dye zeolite nay

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