The DOI matches its Crossref record; 2 of the 2 references it cites were found in a registry or an index.
Labeling Live Cells by Copper-Catalyzed Alkyne−Azide Click Chemistry
Open accessAbstract
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.
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Citations
Cites
Neurodegenerative diseases and oxidative stress
Barnham, K. J., Masters, C. L., & Bush, A. I. (2004) · Nature Reviews Drug Discovery · doi:10.1038/nrd1330 · Cited by 3,683 · cited 1×
“The Cu/ascorbate system is a prodigious generator of oxygen radicals and other reactive species in air (33-38).”
BackgroundRapid Cu-free click chemistry with readily synthesized biarylazacyclooctynones
Jewett, J. C., Sletten, E. M., & Bertozzi, C. R. (2010) · Journal of the American Chemical Society · doi:10.1021/ja100014q · Cited by 697
Cited by
Click Chemistry for Drug Development and Diverse Chemical–Biology Applications
Thirumurugan, P., Matosiuk, D., & Jozwiak, K. (2013) · Chemical Reviews · doi:10.1021/cr200409f · Cited by 1,896
Click Chemistry in Complex Mixtures: Bioorthogonal Bioconjugation
McKay, C. S., & Finn, M. G. (2014) · Chemistry & Biology · doi:10.1016/j.chembiol.2014.09.002 · Cited by 768
Self-citationScinto, S. L., Bilodeau, D. A., Hincapie, R., Lee, W., Nguyen, S. S., Xu, M., am Ende, C. W., Finn, M. G., Lang, K., Lin, Q., et al. (2021) · Nature Reviews Methods Primers · doi:10.1038/s43586-021-00028-z · Cited by 592
Self-citationBioorthogonal Reactions for Labeling Proteins
Lang, K., & Chin, J. W. (2014) · ACS Chemical Biology · doi:10.1021/cb4009292 · Cited by 555
Cu(I)-Catalyzed Click Chemistry in Glycoscience and Their Diverse Applications
Agrahari, A. K., Bose, P., Jaiswal, M. K., Rajkhowa, S., Singh, A. S., Hotha, S., Mishra, N., & Tiwari, V. K. (2021) · Chemical Reviews · doi:10.1021/acs.chemrev.0c00920 · Cited by 445
Copper‐Catalyzed Azide–Alkyne Click Chemistry for Bioconjugation
Presolski, S. I., Hong, V. P., & Finn, M. G. (2011) · Current Protocols in Chemical Biology · doi:10.1002/9780470559277.ch110148 · Cited by 416
Self-citationCellular Consequences of Copper Complexes Used To Catalyze Bioorthogonal Click Reactions
Kennedy, D. C., McKay, C. S., Legault, M. C. B., Danielson, D. C., Blake, J. A., Pegoraro, A. F., Stolow, A., Mester, Z., & Pezacki, J. P. (2011) · Journal of the American Chemical Society · doi:10.1021/ja2083027 · Cited by 416
Recent Fascinating Aspects of the CuAAC Click Reaction
Meldal, M., & Diness, F. (2020) · Trends in Chemistry · doi:10.1016/j.trechm.2020.03.007 · Cited by 266
Diels–Alder Cycloaddition for Fluorophore Targeting to Specific Proteins inside Living Cells
Liu, D. S., Tangpeerachaikul, A., Selvaraj, R., Taylor, M. T., Fox, J. M., & Ting, A. Y. (2012) · Journal of the American Chemical Society · doi:10.1021/ja209325n · Cited by 254
Metadata
- Authors
- Hong, V., Steinmetz, N. F., Manchester, M., & Finn, M. G.
- Venue
- Bioconjugate Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 2010-10-01
- Volume
- 21
- Issue
- 10
- Pages
- 1912-1916
- ISSN
- 1043-1802 (ISSN-L)
- 1520-4812
- OpenAlex
- W2013821696
- Cited by
- 432
- References
- 2
- FWCI
- 11.68
- Type
- journal article
- Language
- en
- Open access
- green
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.
