Evidence map›Paper›PMID 21950520›Full record

ArticleBioconjugate chemistry2011

Synthesis and evaluation of a series of 1,2,4,5-tetrazines for bioorthogonal conjugation.

Mark R Karver, Ralph Weissleder, Scott A Hilderbrand

Abstract read
In one paragraph

Article in Bioconjugate chemistry, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 174 papers.

0numbers the graph read from it
0cells of the map it votes in
174citing papers in PubMed
–field-weighted citation impact
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

174 citing papers in PubMed.

  1. Review
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  7. Review
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  10. Review
  11. Biocompatible Chemistry: A Plug-and-Play Toolbox for Chemical Biology Research.Chembiochem : a European journal of chemical biology · 2025
    Review
  12. Review
  13. Article
  14. Article
  15. Article
  16. Novel Platinum(II) Tetrazine Complex Capable of Live-Cell IEDDA Reaction.Chembiochem : a European journal of chemical biology · 2025
    Article
  17. Article
  18. Article
  19. Article
  20. Article

114 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

3 authors.

Mark R KarverCenter for Systems Biology, Massachusetts General Hospital and Harvard Medical School, 185 Cambridge Street, Boston, MA 02114, USA.
Ralph Weissleder
Scott A Hilderbrand

Funding

StatisticsP50CA086355 · NCI · MASSACHUSETTS GENERAL HOSPITAL · PI WEISSLEDER, MD, PHD, RALPH · 2000 to 2015
$27.8M
Magnetic nanoswitches for sensing biomoleculesR01EB004626 · NIBIB · MASSACHUSETTS GENERAL HOSPITAL · PI WEISSLEDER, MD, PHD, RALPH · 2004 to 2012
$3.2M
Novel Clickdyes for Biomedical SensingR01EB010011 · NIBIB · MASSACHUSETTS GENERAL HOSPITAL · PI WEISSLEDER, MD, PHD, RALPH · 2010 to 2017
$3.1M
NCI NIH HHS P50 CA086355NCI NIH HHS P50CA86355NIBIB NIH HHS R01 EB004626NIBIB NIH HHS R01 EB010011NIBIB NIH HHS R01EB010011
6 · The paper itself

Abstract

1,2,4,5-Tetrazines have been established as effective dienes for inverse electron demand [4 + 2] Diels-Alder cycloaddition reactions with strained alkenes for over 50 years. Recently, this reaction pair combination has been applied to bioorthogonal labeling and cell detection applications; however, to date, there has been no detailed examination and optimization of tetrazines for use in biological experiments. Here, we report the synthesis and characterization of 12 conjugatable tetrazines. The tetrazines were all synthesized in a similar fashion and were screened in parallel to identify candidates most ideally suited for biological studies. In depth follow-up studies revealed compounds with varying degrees of stability and reactivity that could each be useful in different bioorthogonal applications. One promising, highly stable, and water-soluble derivative was used in pretargeted cancer cell labeling studies, confirming its utility as a bioorthogonal moiety.

Indexed as

AlkenesCell Line, TumorClick ChemistryHumansMolecular StructureNorbornanesOrganic ChemicalsStaining and LabelingAlkenesNorbornanesOrganic Chemicals

Identifiers

PMID21950520
PMCPMC3254257

What OpenQuestion holds

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Registered trials

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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.