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Bioconjugation through mesitylene thiol alkylation

AuthorsRamos-Tomillero, Iván; Pérez-Chacón, Gema ; Somovilla-Crespo, Beatriz; Sánchez-Madrid, Francisco; Domínguez, Juan Manuel; Cuevas, Carmen; Zapata, Juan M. ; Rodríguez, Hortensia; Albericio, Fernando
Issue Date2018
PublisherAmerican Chemical Society
CitationBioconjugate Chemistry 29(4): 1199-1208 (2018)
AbstractThe design and generation of complex multifunctional macromolecular structures by bioconjugation is a hot topic due to increasing interest in conjugates with therapeutic applications. In this regard, the development of efficient, selective, and safe conjugation methods is a major objective. In this report, we describe the use of the bis(bromomethyl)benzene scaffold as a linker for bioconjugation with special emphasis on antibody conjugation. We first performed the monothioalkylation of 1,3,5-tris(bromomethyl)benzene, which rendered the reactive dibromotrimethylbenzyl derivatives to be used in thiol bis-alkylation. Next, we introduced into the linker either a bis(Cys)-containing peptide or anti-CD4 and -CD13 monoclonal antibodies, previously subjected to partial reduction of disulfide bonds. Mass spectrometry, UV–vis spectra, and SDS-PAGE experiments revealed that this bis-alkylating agent for bioconjugation preserved both antibody integrity and antibody–antigen binding affinity, as assessed by flow cytometry. Taken together, our results show that the mesitylene scaffold is a suitable linker for thiol-based bioconjugation reactions. This linker could be applicable in the near future for the preparation of antibody drug conjugates.
Publisher version (URL)https://doi.org/10.1021/acs.bioconjchem.7b00828
Identifiersdoi: 10.1021/acs.bioconjchem.7b00828
e-issn: 1520-4812
issn: 1043-1802
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