The DOI matches its Crossref record; 35 of the 35 references it cites were found in a registry or an index.
Copper-free click chemistry in living animals
Open accessAbstract
Chemical reactions that enable selective biomolecule labeling in living organisms offer a means to probe biological processes in vivo. Very few reactions possess the requisite bioorthogonality, and, among these, only the Staudinger ligation between azides and triarylphosphines has been employed for direct covalent modification of biomolecules with probes in the mouse, an important model organism for studies of human disease. Here we explore an alternative bioorthogonal reaction, the 1,3-dipolar cycloaddition of azides and cyclooctynes, also known as “Cu-free click chemistry,” for labeling biomolecules in live mice. Mice were administered peracetylated N -azidoacetylmannosamine (Ac 4 ManNAz) to metabolically label cell-surface sialic acids with azides. After subsequent injection with cyclooctyne reagents, glycoconjugate labeling was observed on isolated splenocytes and in a variety of tissues including the intestines, heart, and liver, with no apparent toxicity. The cyclooctynes tested displayed various labeling efficiencies that likely reflect the combined influence of intrinsic reactivity and bioavailability. These studies establish Cu-free click chemistry as a bioorthogonal reaction that can be executed in the physiologically relevant context of a mouse.
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Self-citationAgard, N. J., Prescher, J. A., & Bertozzi, C. R. (2004) · Journal of the American Chemical Society · doi:10.1021/ja044996f · Cited by 3,017
Self-citationGlycosylation in Cellular Mechanisms of Health and Disease
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Copper-free click chemistry for dynamic in vivo imaging
Baskin, J. M., Prescher, J. A., Laughlin, S. T., Agard, N. J., Chang, P. V., Miller, I. A., Lo, A., Codelli, J. A., & Bertozzi, C. R. (2007) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.0707090104 · Cited by 1,833
Self-citationPrescher, J. A., & Bertozzi, C. R. (2005) · Nature Chemical Biology · doi:10.1038/nchembio0605-13 · Cited by 1,456
Self-citationCycling of O-linked β-N-acetylglucosamine on nucleocytoplasmic proteins
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1.3‐Dipolare Cycloadditionen Rückschau und Ausblick
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In Vivo Imaging of Membrane-Associated Glycans in Developing Zebrafish
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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
Rapid 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
Self-citationAtrp in the design of functional materials for biomedical applications
Siegwart, D. J., Oh, J. K., & Matyjaszewski, K. (2012) · Progress in Polymer Science · doi:10.1016/j.progpolymsci.2011.08.001 · Cited by 613
Scinto, 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
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Metadata
- Authors
- Chang, P. V., Prescher, J. A., Sletten, E. M., Baskin, J. M., Miller, I. A., Agard, N. J., Lo, A., & Bertozzi, C. R.
- Venue
- Proceedings of the National Academy of Sciences
- Published
- 2010-01-14
- Volume
- 107
- Issue
- 5
- Pages
- 1821-1826
- ISSN
- 0027-8424 (ISSN-L)
- 1091-6490
- OpenAlex
- W1989368359
- Cited by
- 655
- References
- 35
- FWCI
- 28.10
- Type
- journal article
- Language
- en
- Open access
- green
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- Chang, P. V., Prescher, J. A., Sletten, E. M., Baskin, J. M., Miller, I. A., Agard, N. J., Lo, A., & Bertozzi, C. R. (2010). Copper-free click chemistry in living animals. Proceedings of the National Academy of Sciences. https://doi.org/10.1073/pnas.0911116107
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