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Stoichiometric and irreversible cysteine-selective protein modification using carbonylacrylic reagents

AutorBernardim, Barbara; Corzana, Francisco; Jiménez-Osés, Gonzalo ; Bernardes, Gonçalo J. L.
Fecha de publicación2016
EditorNature Publishing Group
CitaciónNature Communications 7: 13128 (2016)
ResumenMaleimides remain the reagents of choice for the preparation of therapeutic and imaging protein conjugates despite the known instability of the resulting products that undergo thiol-exchange reactions in vivo. Here we present the rational design of carbonylacrylic reagents for chemoselective cysteine bioconjugation. These reagents undergo rapid thiol Michael-addition under biocompatible conditions in stoichiometric amounts. When using carbonylacrylic reagents equipped with PEG or fluorophore moieties, this method enables access to protein and antibody conjugates precisely modified at pre-determined sites. Importantly, the conjugates formed are resistant to degradation in plasma and are biologically functional, as demonstrated by the selective imaging and detection of apoptotic and HER2+ cells, respectively. The straightforward preparation, stoichiometric use and exquisite cysteine selectivity of the carbonylacrylic reagents combined with the stability of the products and the availability of biologically relevant cysteine-tagged proteins make this method suitable for the routine preparation of chemically defined conjugates for in vivo applications.
DescripciónThis work is licensed under a Creative Commons Attribution 4.0 International License.-- et al.
Versión del editorhttps://doi.org/10.1038/ncomms13128
URIhttp://hdl.handle.net/10261/155724
DOI10.1038/ncomms13128
Identificadoresdoi: 10.1038/ncomms13128
e-issn: 2041-1723
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