Evidence map›Paper›PMID 31341960›Full record

ArticleCommunications biology2019

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

Gerti Beliu, Andreas J Kurz, Alexander C Kuhlemann, Lisa Behringer-Pliess, Mara Meub, Natalia Wolf, Jürgen Seibel, Zhen-Dan Shi, Martin Schnermann, Jonathan B Grimm and 3 more

Open access · goldAbstract read
In one paragraph

Article in Communications biology, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 81 papers.

0numbers the graph read from it
0cells of the map it votes in
81citing papers in PubMed
8.6field-weighted citation impact, top 1% of its field
1 · What the graph read from it

What it found

Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.

The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.

2 · The registry

The trial behind it

Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.

Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.

3 · Its place in the literature

Who cites it

81 citing papers in PubMed, 152 citations in OpenAlex.

  1. Bioorthogonal Chemistry in Neurobiology: From Imaging to Proteomics.Chembiochem : a European journal of chemical biology · 2026
    Review
  2. Nanorulers for Super-Resolution Microscopy.Chembiochem : a European journal of chemical biology · 2026
    Review
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21 more citing papers are in PubMed but not listed here.

4 · The record

Corrections and comments

PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.

5 · Who and what money

Authors and funding

13 authors at 4 institutions in 2 countries.

Gerti Beliu1Department of Biotechnology and Biophysics, Biocenter, University of Würzburg, Am Hubland, 97074 Würzburg, Germany.
Andreas J Kurz1Department of Biotechnology and Biophysics, Biocenter, University of Würzburg, Am Hubland, 97074 Würzburg, Germany.
Alexander C Kuhlemann1Department of Biotechnology and Biophysics, Biocenter, University of Würzburg, Am Hubland, 97074 Würzburg, Germany.
Lisa Behringer-Pliess1Department of Biotechnology and Biophysics, Biocenter, University of Würzburg, Am Hubland, 97074 Würzburg, Germany.
Mara Meub1Department of Biotechnology and Biophysics, Biocenter, University of Würzburg, Am Hubland, 97074 Würzburg, Germany.
Natalia Wolf2Institute of Organic Chemistry, University of Würzburg, Am Hubland, 97074 Würzburg, Germany.
Jürgen Seibel2Institute of Organic Chemistry, University of Würzburg, Am Hubland, 97074 Würzburg, Germany.
Zhen-Dan Shi3Imaging Probe Development Center, National Heart, Lung, and Blood Institute, National Institutes of Health, Rockville, MD 20850 USA.
Martin Schnermann4Center for Cancer Research, Chemical Biology Laboratory, National Cancer Institute, Frederick, MD 21702 USA.
Jonathan B Grimm5Janelia Research Campus, Howard Hughes Medical Institute, 19700 Helix Drive, Ashburn, VA 20147 USA.
Luke D Lavis5Janelia Research Campus, Howard Hughes Medical Institute, 19700 Helix Drive, Ashburn, VA 20147 USA.ORCID 0000-0002-0789-6343
Sören Doose1Department of Biotechnology and Biophysics, Biocenter, University of Würzburg, Am Hubland, 97074 Würzburg, Germany.
Markus Sauer1Department of Biotechnology and Biophysics, Biocenter, University of Würzburg, Am Hubland, 97074 Würzburg, Germany.
University of Würzburg · DEHoward Hughes Medical Institute · USFrederick National Laboratory for Cancer Research · USNational Institutes of Health · US

Funding

Howard Hughes Medical Institute
6 · The paper itself

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.

Indexed as

Genetic CodeAnimalsChlorocebus aethiopsColoring AgentsCOS CellsCycloaddition ReactionCyclooctanesFluorescent DyesHEK293 CellsHeterocyclic CompoundsHeterocyclic Compounds, 1-RingHumansMicroscopy, ConfocalOptical ImagingRhodaminesStaining and LabelingColoring AgentsCyclooctanesFluorescent DyesHeterocyclic CompoundsHeterocyclic Compounds, 1-RingRhodaminesBiological fluorescenceBiophysical chemistry

Identifiers

PMID31341960
PMCPMC6642216
OpenAlexW2963193903

What OpenQuestion holds

Textmetadata
LicenceCC BY
Read underepoch 390

Registered trials

None linked

Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.