The DOI matches its Crossref record; 117 of the 117 references it cites were found in a registry or an index.
Practical Considerations, Challenges, and Limitations of Bioconjugation via Azide–Alkyne Cycloaddition
Open accessAbstract
Interrogating biological systems is often limited by access to biological probes. The emergence of "click chemistry" has revolutionized bioconjugate chemistry by providing facile reaction conditions amenable to both biologic molecules and small molecule probes such as fluorophores, toxins, or therapeutics. One particularly popular version is the copper-catalyzed azide-alkyne cycloaddition (AAC) reaction, which has spawned new alternatives such as the strain-promoted azide-alkyne cycloaddition reaction, among others. This focused review highlights practical approaches to AAC reactions for the synthesis of peptide or protein bioconjugates and contrasts current challenges and limitations in light of recent advances in the field. The conical success of antibody drug conjugates has expanded the toolbox of linkers and payloads to facilitate practical applications of bioconjugation to create novel therapeutics and biologic probes. The AAC reaction in particular is poised to enable a large set of functionalized molecules as a combinatorial approach to high-throughput bioconjugate generation, screening, and honing of lead compounds.
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Cites
Tornøe, C. W., Christensen, C., & Meldal, M. (2002) · The Journal of Organic Chemistry · doi:10.1021/jo011148j · Cited by 8,696
Agard, N. J., Prescher, J. A., & Bertozzi, C. R. (2004) · Journal of the American Chemical Society · doi:10.1021/ja044996f · Cited by 3,017
1,3‐Dipolar Cycloadditions. Past and Future
Huisgen, R. (1963) · Angewandte Chemie International Edition in English · doi:10.1002/anie.196305651 · Cited by 2,929
Strategies and challenges for the next generation of antibody–drug conjugates
Beck, A., Goetsch, L., Dumontet, C., & Corvaïa, N. (2017) · Nature Reviews Drug Discovery · doi:10.1038/nrd.2016.268 · Cited by 2,271
Hein, J. E., & Fokin, V. V. (2010) · Chemical Society Reviews · doi:10.1039/b904091a · Cited by 2,198
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
Himo, F., Lovell, T., Hilgraf, R., Rostovtsev, V. V., Noodleman, L., Sharpless, K. B., & Fokin, V. V. (2005) · Journal of the American Chemical Society · doi:10.1021/ja0471525 · Cited by 1,738
Targeting HER2-Positive Breast Cancer with Trastuzumab-DM1, an Antibody–Cytotoxic Drug Conjugate
Lewis Phillips, G. D., Li, G., Dugger, D. L., Crocker, L. M., Parsons, K. L., Mai, E., Blättler, W. A., Lambert, J. M., Chari, R. V. J., Lutz, R. J., et al. (2008) · Cancer Research · doi:10.1158/0008-5472.can-08-1776 · Cited by 1,676
The Thiol-Michael Addition Click Reaction: A Powerful and Widely Used Tool in Materials Chemistry
Nair, D. P., Podgórski, M., Chatani, S., Gong, T., Xi, W., Fenoli, C. R., & Bowman, C. N. (2014) · Chemistry of Materials · doi:10.1021/cm402180t · Cited by 1,596
CuI‐Catalyzed Alkyne–Azide “Click” Cycloadditions from a Mechanistic and Synthetic Perspective
Bock, V. D., Hiemstra, H., & van Maarseveen, J. H. (2006) · European Journal of Organic Chemistry · doi:10.1002/ejoc.200500483 · Cited by 1,452
Cited by
A Hitchhiker’s Guide to Click-Chemistry with Nucleic Acids
Fantoni, N. Z., El-Sagheer, A. H., & Brown, T. (2021) · Chemical Reviews · doi:10.1021/acs.chemrev.0c00928 · Cited by 462
Click Chemistry in Proteomic Investigations
Parker, C. G., & Pratt, M. R. (2020) · Cell · doi:10.1016/j.cell.2020.01.025 · Cited by 380
Gautam, M., Jozic, A., Su, G. L.-N., Herrera-Barrera, M., Curtis, A., Arrizabalaga, S., Tschetter, W., Ryals, R. C., & Sahay, G. (2023) · Nature Communications · doi:10.1038/s41467-023-42189-3 · Cited by 123
Metadata
- Authors
- Pickens, C. J., Johnson, S. N., Pressnall, M. M., Leon, M. A., & Berkland, C. J.
- Venue
- Bioconjugate Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 2017-12-29
- Volume
- 29
- Issue
- 3
- Pages
- 686-701
- ISSN
- 1043-1802 (ISSN-L)
- 1520-4812
- OpenAlex
- W2779122303
- Cited by
- 285
- References
- 117
- FWCI
- 10.61
- Type
- journal article
- Language
- en
- Open access
- green
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- Pickens, C. J., Johnson, S. N., Pressnall, M. M., Leon, M. A., & Berkland, C. J. (2018). Practical Considerations, Challenges, and Limitations of Bioconjugation via Azide–Alkyne Cycloaddition. Bioconjugate Chemistry. https://doi.org/10.1021/acs.bioconjchem.7b00633
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