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dc.contributor.authorRamos-Tomillero, Iván-
dc.contributor.authorPérez-Chacón, Gema-
dc.contributor.authorSomovilla-Crespo, Beatriz-
dc.contributor.authorSánchez-Madrid, Francisco-
dc.contributor.authorDomínguez, Juan Manuel-
dc.contributor.authorCuevas, Carmen-
dc.contributor.authorZapata, Juan M.-
dc.contributor.authorRodríguez, Hortensia-
dc.contributor.authorAlbericio, Fernando-
dc.date.accessioned2018-08-20T11:46:48Z-
dc.date.available2018-08-20T11:46:48Z-
dc.date.issued2018-
dc.identifierdoi: 10.1021/acs.bioconjchem.7b00828-
dc.identifiere-issn: 1520-4812-
dc.identifierissn: 1043-1802-
dc.identifier.citationBioconjugate Chemistry 29(4): 1199-1208 (2018)-
dc.identifier.urihttp://hdl.handle.net/10261/168917-
dc.description.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.-
dc.description.sponsorshipI.R-T. thanks the Generalitat de Catalunya for a predoctoral fellowship. This work was funded in part by the following: the Ministerio de Economia y Competitividad (MINECO) and European Regional Development’s funds (ERDF) - Programa INNPACTO, project MarinMab (IPT-2012-0198-090000), the Generalitat de Catalunya (2014 SGR 137), and the Institute for Research in Biomedicine Barcelona (IRB Barcelona) (Spain), and the National Research Foundation (NRF) (Blue Sky’s Research Programme # 110960) (South Africa).-
dc.publisherAmerican Chemical Society-
dc.relation.isversionofPostprint-
dc.rightsopenAccessen_EN
dc.titleBioconjugation through mesitylene thiol alkylation-
dc.typeartículo-
dc.relation.publisherversionhttps://doi.org/10.1021/acs.bioconjchem.7b00828-
dc.date.updated2018-08-20T11:46:48Z-
dc.description.versionPeer Reviewed-
dc.language.rfc3066eng-
dc.contributor.funderInstitute for Research in Biomedicine (Spain)-
dc.contributor.funderNational Research Foundation (South Africa)-
dc.contributor.funderEuropean Commission-
dc.contributor.funderMinisterio de Economía y Competitividad (España)-
dc.contributor.funderGeneralitat de Catalunya-
dc.relation.csic-
dc.identifier.funderhttp://dx.doi.org/10.13039/501100002809es_ES
dc.identifier.funderhttp://dx.doi.org/10.13039/501100001321es_ES
dc.identifier.funderhttp://dx.doi.org/10.13039/501100000780es_ES
dc.identifier.funderhttp://dx.doi.org/10.13039/501100003329es_ES
dc.identifier.funderhttp://dx.doi.org/10.13039/100007678es_ES
dc.identifier.pmid29433317-
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