Evidence map›Paper›PMID 22176354›Full record

ArticleJournal of the American Chemical Society2012

Diels-Alder cycloaddition for fluorophore targeting to specific proteins inside living cells.

Daniel S Liu, Anupong Tangpeerachaikul, Ramajeyam Selvaraj, Michael T Taylor, Joseph M Fox, Alice Y Ting

Abstract read
In one paragraph

Article in Journal of the American Chemical Society, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 89 papers.

0numbers the graph read from it
0cells of the map it votes in
89citing 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

89 citing papers in PubMed.

  1. Review
  2. Tetrazine-Inorganic chemistry frontiers · 2026
    Article
  3. Article
  4. Article
  5. Article
  6. Article
  7. Review
  8. Review
  9. Review
  10. Article
  11. Article
  12. Promiscuous Enzymes for Residue-Specific Peptide and Protein Late-Stage Functionalization.Chembiochem : a European journal of chemical biology · 2023
    Review
  13. Article
  14. Article
  15. Bioconjugate chemistry · 2023
    Article
  16. Article
  17. HIV infection detection using CRISPR/Cas systems: Present and future prospects.Computational and structural biotechnology journal · 2023
    Review
  18. Article
  19. Article
  20. Article

29 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

6 authors.

Daniel S LiuDepartment of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139, USA.
Anupong Tangpeerachaikul
Ramajeyam Selvaraj
Michael T Taylor
Joseph M Fox
Alice Y Ting

Funding

UDE COBRE: STRAINED MOLECULES FOR SYNTHESIS OF UNNATURAL AMINO ACIDSP20RR017716 · NCRR · UNIVERSITY OF DELAWARE · PI SULLIVAN, MILLICENT O · 2002 to 2011
$16.9M
Specific protein labeling in cells with engineered BirAR01GM072670 · NIGMS · MASSACHUSETTS INSTITUTE OF TECHNOLOGY · PI TING, ALICE Y · 2005 to 2013
$2.7M
NCRR NIH HHS P20 RR017716NIGMS NIH HHS R01 GM072670
6 · The paper itself

Abstract

The inverse-electron-demand Diels-Alder cycloaddition between trans-cyclooctenes and tetrazines is biocompatible and exceptionally fast. We utilized this chemistry for site-specific fluorescence labeling of proteins on the cell surface and inside living mammalian cells by a two-step protocol. Escherichia coli lipoic acid ligase site-specifically ligates a trans-cyclooctene derivative onto a protein of interest in the first step, followed by chemoselective derivatization with a tetrazine-fluorophore conjugate in the second step. On the cell surface, this labeling was fluorogenic and highly sensitive. Inside the cell, we achieved specific labeling of cytoskeletal proteins with green and red fluorophores. By incorporating the Diels-Alder cycloaddition, we have broadened the panel of fluorophores that can be targeted by lipoic acid ligase.

Indexed as

Drug Delivery SystemsEscherichia coliFluorescent DyesHEK293 CellsHumansLigasesMolecular StructureProteinsFluorescent DyesLigasesProteins

Identifiers

PMID22176354
PMCPMC3381951

What OpenQuestion holds

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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.