The DOI matches its Crossref record; 32 of the 32 references it cites were found in a registry or an index.
Alkynyl sugar analogs for the labeling and visualization of glycoconjugates in cells
Open accessAbstract
Developing tools for investigating the cellular activity of glycans will help to delineate the molecular basis for aberrant glycosylation in pathological processes such as cancer. Metabolic oligosaccharide engineering, which inserts sugar-reporting groups into cellular glycoconjugates, represents a powerful method for imaging the localization, trafficking, and dynamics of glycans and isolating them for glyco-proteomic analysis. Herein, we show that the alkyne-reporting group can be incorporated into cellular glycans. The alkyne group is a small, inert, bio-orthogonal handle that can be chemoselectively labeled by using the Cu(I) catalyzed [3 + 2] azide-alkyne cycloaddition, or click chemistry. Alkynyl sugar monomers, based on fucose (Fuc) and N -acetylmannosamine (ManNAc), were incorporated into fucosylated and sialylated glycans in several cancer cell lines, allowing for cell surface and intracellular visualization of glycoconjugates, as well as, observation of alkyne-bearing glycoproteins. Similarly to our previous results with an azido Fuc/alkynyl probe system, we demonstrated that click-activated fluorogenic probes are practical tools for efficiently and selectively labeling alkynyl-modified glycans. Because Fuc and sialic acid are terminal glycan residues with a notably increased presence in many tumors, we hope that our method will provide useful information about their roles in cancer and ultimately can be used for diagnostic and therapeutic purposes.
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Cites
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Bioconjugation by Copper(I)-Catalyzed Azide-Alkyne [3 + 2] Cycloaddition
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Profiling Enzyme Activities In Vivo Using Click Chemistry Methods
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A Comparative Study of Bioorthogonal Reactions with Azides
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A Fluorogenic 1,3-Dipolar Cycloaddition Reaction of 3-Azidocoumarins and Acetylenes
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Cited by
Bioorthogonal Chemistry: Fishing for Selectivity in a Sea of Functionality
Sletten, E. M., & Bertozzi, C. R. (2009) · Angewandte Chemie International Edition · doi:10.1002/anie.200900942 · Cited by 3,165
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
Liu, Y.-C., Yen, H.-Y., Chen, C.-Y., Chen, C.-H., Cheng, P.-F., Juan, Y.-H., Chen, C.-H., Khoo, K.-H., Yu, C.-J., Yang, P.-C., et al. (2011) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.1107385108 · Cited by 424
Self-citationBioorthogonal Chemistry and Its Applications
Bird, R. E., Lemmel, S. A., Yu, X., & Zhou, Q. A. (2021) · Bioconjugate Chemistry · doi:10.1021/acs.bioconjchem.1c00461 · Cited by 409
Click Chemistry in Proteomic Investigations
Parker, C. G., & Pratt, M. R. (2020) · Cell · doi:10.1016/j.cell.2020.01.025 · Cited by 380
Metadata
- Authors
- Hsu, T.-L., Hanson, S. R., Kishikawa, K., Wang, S.-K., Sawa, M., & Wong, C.-H.
- Venue
- Proceedings of the National Academy of Sciences
- Published
- 2007-02-20
- Volume
- 104
- Issue
- 8
- Pages
- 2614-2619
- ISSN
- 0027-8424 (ISSN-L)
- 1091-6490
- OpenAlex
- W4248522153
- Cited by
- 319
- References
- 32
- FWCI
- 11.98
- Type
- journal article
- Language
- en
- Open access
- green
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- Hsu, T.-L., Hanson, S. R., Kishikawa, K., Wang, S.-K., Sawa, M., & Wong, C.-H. (2007). Alkynyl sugar analogs for the labeling and visualization of glycoconjugates in cells. Proceedings of the National Academy of Sciences. https://doi.org/10.1073/pnas.0611307104
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