Evidence map›Paper›PMID 20886827›Full record

ArticleBioconjugate chemistry2010

Labeling live cells by copper-catalyzed alkyne--azide click chemistry.

Vu Hong, Nicole F Steinmetz, Marianne Manchester, M G Finn

Abstract read
In one paragraph

Article in Bioconjugate chemistry, 2010. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 156 papers.

0numbers the graph read from it
0cells of the map it votes in
156citing papers in PubMed
12.6field-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

156 citing papers in PubMed, 400 citations in OpenAlex.

  1. Review
  2. Review
  3. Article
  4. Review
  5. Article
  6. Article
  7. Article
  8. Review
  9. The Copper-Catalyzed Azide-Alkyne Cycloaddition Reaction: Why Two Is Faster than One.Chemphyschem : a European journal of chemical physics and physical chemistry · 2026
    Article
  10. Review
  11. Article
  12. Article
  13. Photoactivatable Alkyne Tag for Photolabeling Biomolecules in Living Cells.Chembiochem : a European journal of chemical biology · 2025
    Article
  14. Review
  15. Review
  16. Article
  17. Article
  18. Article
  19. Review
  20. Review

96 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

4 authors at 2 institutions in 1 country.

Vu HongDepartment of Cell Biology, The Scripps Research Institute, La Jolla, California, USA.
Nicole F Steinmetz
Marianne Manchester
M G Finn
University of California, San Diego · USScripps Research Institute · US

Funding

USING VIRAL NANOPARTICLES TO TARGET CANCERR01CA112075 · NCI · UNIVERSITY OF CALIFORNIA, SAN DIEGO · PI MANCHESTER, MARIANNE · 2005 to 2009
$3.7M
Viral nanoparticles as platforms for the design of novel targeted therapeuticsK99EB009105 · NIBIB · SCRIPPS RESEARCH INSTITUTE, THE · PI STEINMETZ, NICOLE FRANZISKA · 2009 to 2010
$97k
NCI NIH HHS R01 CA112075NIBIB NIH HHS K99 EB009105
6 · The paper itself

Abstract

The copper-catalyzed azide-alkyne cycloaddition (CuAAC) reaction, optimized for biological molecules in aqueous buffers, has been shown to rapidly label mammalian cells in culture with no loss in cell viability. Metabolic uptake and display of the azide derivative of N-acetylmannosamine developed by Bertozzi, followed by CuAAC ligation using sodium ascorbate and the ligand tris(hydroxypropyltriazolyl)methylamine (THPTA), gave rise to abundant covalent attachment of dye-alkyne reactants. THPTA serves both to accelerate the CuAAC reaction and to protect the cells from damage by oxidative agents produced by the Cu-catalyzed reduction of oxygen by ascorbate, which is required to maintain the metal in the active +1 oxidation state. This procedure extends the application of this fastest of azide-based bioorthogonal reactions to the exterior of living cells.

Indexed as

Click ChemistryAlkynesAnimalsAscorbic AcidAzidesCatalysisCell SurvivalCHO CellsCopperCricetinaeCricetulusHeLa CellsHumansJurkat CellsPolysaccharidesStaining and LabelingAlkynesAscorbic AcidAzidesCopperPolysaccharides

Identifiers

PMID20886827
PMCPMC3014321
OpenAlexW2013821696

What OpenQuestion holds

Textmetadata
LicenceTDM
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.