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Cysteine-Reactive Polymers Synthesized by Atom Transfer Radical Polymerization for Conjugation to Proteins
Abstract
In this communication we report a strategy for the synthesis of semitelechelic polymers reactive to cysteines. An initiator modified with a pyridyl disulfide was prepared and used for the CuBr/2,2'-bipyridine-mediated atom transfer radical polymerization (ATRP) of 2-hydroxyethyl methacrylate. Polydispersity indices (M(w)/M(n)) of the polymers with different molecular weights were 1.25 or less. The pyridyl disulfide end group was preserved during the polymerization and allowed direct conjugation of the polymer to cysteine residues of bovine serum albumin. The described method provides a general way for the preparation of protein-polymer conjugates through a reversible disulfide bond without the need for postsynthesis modification of the polymers.
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Citations
Cited by
Controlled/living radical polymerization: Features, developments, and perspectives
Braunecker, W. A., & Matyjaszewski, K. (2007) · Progress in Polymer Science · doi:10.1016/j.progpolymsci.2006.11.002 · Cited by 3,202
Atom Transfer Radical Polymerization (ATRP): Current Status and Future Perspectives
Matyjaszewski, K. (2012) · Macromolecules · doi:10.1021/ma3001719 · Cited by 2,606
Nanostructured functional materials prepared by atom transfer radical polymerization
Matyjaszewski, K., & Tsarevsky, N. V. (2009) · Nature Chemistry · doi:10.1038/nchem.257 · Cited by 1,258
Ouchi, M., Terashima, T., & Sawamoto, M. (2009) · Chemical Reviews · doi:10.1021/cr900234b · Cited by 1,257
Macromolecular Engineering by Atom Transfer Radical Polymerization
Matyjaszewski, K., & Tsarevsky, N. V. (2014) · Journal of the American Chemical Society · doi:10.1021/ja408069v · Cited by 1,159
Bioapplications of RAFT Polymerization
Boyer, C., Bulmus, V., Davis, T. P., Ladmiral, V., Liu, J., & Perrier, S. (2009) · Chemical Reviews · doi:10.1021/cr9001403 · Cited by 1,015
Controlled/living radical polymerization
Matyjaszewski, K., & Spanswick, J. (2005) · Materials Today · doi:10.1016/s1369-7021(05)00745-5 · Cited by 746
Therapeutic Protein–Polymer Conjugates: Advancing Beyond PEGylation
Pelegri-O’Day, E. M., Lin, E.-W., & Maynard, H. D. (2014) · Journal of the American Chemical Society · doi:10.1021/ja504390x · Cited by 622
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
In Situ Preparation of Protein−“Smart” Polymer Conjugates with Retention of Bioactivity
Heredia, K. L., Bontempo, D., Ly, T., Byers, J. T., Halstenberg, S., & Maynard, H. D. (2005) · Journal of the American Chemical Society · doi:10.1021/ja054482w · Cited by 451
Self-citationWell-Defined Protein−Polymer Conjugates via in Situ RAFT Polymerization
Boyer, C., Bulmus, V., Liu, J., Davis, T. P., Stenzel, M. H., & Barner-Kowollik, C. (2007) · Journal of the American Chemical Society · doi:10.1021/ja070956a · Cited by 411
Use of ascorbic acid as reducing agent for synthesis of well-defined polymers by arget atrp
Min, K., Gao, H., & Matyjaszewski, K. (2007) · Macromolecules · doi:10.1021/ma0702041 · Cited by 380
Synthesis of protein–polymer conjugates
Heredia, K. L., & Maynard, H. D. (2007) · Org. Biomol. Chem. · doi:10.1039/b612355d · Cited by 324
Self-citationSurface functionalization of biomaterials by radical polymerization
Zhou, T., Zhu, Y., Li, X., Liu, X., Yeung, K. W. K., Wu, S., Wang, X., Cui, Z., Yang, X., & Chu, P. K. (2016) · Progress in Materials Science · doi:10.1016/j.pmatsci.2016.04.005 · Cited by 145
Metadata
- Authors
- Bontempo, D., Heredia, K. L., Fish, B. A., & Maynard, H. D.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2004-11-04
- Volume
- 126
- Issue
- 47
- Pages
- 15372-15373
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2037072498
- Cited by
- 297
- References
- 0
- FWCI
- 12.08
- Type
- journal article
- Language
- en
- Open access
- closed
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