Controlled In-Cell Generation of Active Palladium(0) Species for Bioorthogonal Decaging

Owing to their bioorthogonality, transition metals have become very popular in the development of biocompatible bond cleavage reactions. However, many approaches require design and synthesis of complex ligands or formulation of nanoparticles which often perform poorly in living cells. This work repo...

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Autores: Konč, Juraj, Sabatino, Valerio, Jiménez-Moreno, Ester, Latocheski, Eloah, Rodríguez Pérez, Laura, Day, Jason, Domingos, Josiel B., Bernardes, Gonçalo J. L.
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2022
País:España
Institución:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/344525
Acceso en línea:http://hdl.handle.net/10261/344525
Access Level:acceso abierto
Palabra clave:bioorthogonal
bond-cleavage
decaging
palladium
cancer
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spelling Controlled In-Cell Generation of Active Palladium(0) Species for Bioorthogonal DecagingKonč, JurajSabatino, ValerioJiménez-Moreno, EsterLatocheski, EloahRodríguez Pérez, LauraDay, JasonDomingos, Josiel B.Bernardes, Gonçalo J. L.bioorthogonalbond-cleavagedecagingpalladiumcancerOwing to their bioorthogonality, transition metals have become very popular in the development of biocompatible bond cleavage reactions. However, many approaches require design and synthesis of complex ligands or formulation of nanoparticles which often perform poorly in living cells. This work reports on a method for the generation of an active palladium species that triggers bond cleaving reactions inside living cells. We utilized the water-soluble Na2PdCl4 as a simple source of Pd(II) which can be intracellularly reduced by sodium ascorbate to the active Pd(0) species. Once generated, Pd(0) triggers the cleavage of allyl ether and carbamate caging groups leading to the release of biologically active molecules. These findings do not only expand the toolbox of available bioorthogonal dissociative reactions but also provide an additional strategy for controlling the reactivity of Pd species involved in Pd mediated bioorthogonal reactionsThis project has received funding from the European Research Council (ERC) under the European Union’s Horizon 2020 research and innovation programme (Grant agreement No. 676832), the European Commission (Marie-Skłodowska-Curie Actions IEF to E.J.M., Grant agreement No. 701473), FCT Portugal (Stimulus CEECIND/00453/2018 to G.J.L.B) and CAPES PrInt Call – Program for Institutional Internationalization (88887.310560/2018-00). The authors would also like to thank Dr. Vikki Cantrill for her help with the editing of this manuscript and Claudia Flandoli (draw.science) for editing the figuresPeer reviewedWiley-VCHEuropean Commission202420242022info:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_6501Postprintinfo:eu-repo/semantics/acceptedVersionhttp://hdl.handle.net/10261/344525reponame:DIGITAL.CSIC. Repositorio Institucional del CSICinstname:Consejo Superior de Investigaciones Científicas (CSIC)Inglés#PLACEHOLDER_PARENT_METADATA_VALUE##PLACEHOLDER_PARENT_METADATA_VALUE#info:eu-repo/grantAgreement/EC/H2020/676832info:eu-repo/grantAgreement/EC/HE/701473https://doi.org/10.1002/anie.202113519Noinfo:eu-repo/semantics/openAccessoai:digital.csic.es:10261/3445252026-05-22T06:33:51Z
dc.title.none.fl_str_mv Controlled In-Cell Generation of Active Palladium(0) Species for Bioorthogonal Decaging
title Controlled In-Cell Generation of Active Palladium(0) Species for Bioorthogonal Decaging
spellingShingle Controlled In-Cell Generation of Active Palladium(0) Species for Bioorthogonal Decaging
Konč, Juraj
bioorthogonal
bond-cleavage
decaging
palladium
cancer
title_short Controlled In-Cell Generation of Active Palladium(0) Species for Bioorthogonal Decaging
title_full Controlled In-Cell Generation of Active Palladium(0) Species for Bioorthogonal Decaging
title_fullStr Controlled In-Cell Generation of Active Palladium(0) Species for Bioorthogonal Decaging
title_full_unstemmed Controlled In-Cell Generation of Active Palladium(0) Species for Bioorthogonal Decaging
title_sort Controlled In-Cell Generation of Active Palladium(0) Species for Bioorthogonal Decaging
dc.creator.none.fl_str_mv Konč, Juraj
Sabatino, Valerio
Jiménez-Moreno, Ester
Latocheski, Eloah
Rodríguez Pérez, Laura
Day, Jason
Domingos, Josiel B.
Bernardes, Gonçalo J. L.
author Konč, Juraj
author_facet Konč, Juraj
Sabatino, Valerio
Jiménez-Moreno, Ester
Latocheski, Eloah
Rodríguez Pérez, Laura
Day, Jason
Domingos, Josiel B.
Bernardes, Gonçalo J. L.
author_role author
author2 Sabatino, Valerio
Jiménez-Moreno, Ester
Latocheski, Eloah
Rodríguez Pérez, Laura
Day, Jason
Domingos, Josiel B.
Bernardes, Gonçalo J. L.
author2_role author
author
author
author
author
author
author
dc.contributor.none.fl_str_mv European Commission
dc.subject.none.fl_str_mv bioorthogonal
bond-cleavage
decaging
palladium
cancer
topic bioorthogonal
bond-cleavage
decaging
palladium
cancer
description Owing to their bioorthogonality, transition metals have become very popular in the development of biocompatible bond cleavage reactions. However, many approaches require design and synthesis of complex ligands or formulation of nanoparticles which often perform poorly in living cells. This work reports on a method for the generation of an active palladium species that triggers bond cleaving reactions inside living cells. We utilized the water-soluble Na2PdCl4 as a simple source of Pd(II) which can be intracellularly reduced by sodium ascorbate to the active Pd(0) species. Once generated, Pd(0) triggers the cleavage of allyl ether and carbamate caging groups leading to the release of biologically active molecules. These findings do not only expand the toolbox of available bioorthogonal dissociative reactions but also provide an additional strategy for controlling the reactivity of Pd species involved in Pd mediated bioorthogonal reactions
publishDate 2022
dc.date.none.fl_str_mv 2022
2024
2024
dc.type.none.fl_str_mv info:eu-repo/semantics/article
http://purl.org/coar/resource_type/c_6501
Postprint
info:eu-repo/semantics/acceptedVersion
format article
status_str acceptedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10261/344525
url http://hdl.handle.net/10261/344525
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv #PLACEHOLDER_PARENT_METADATA_VALUE#
#PLACEHOLDER_PARENT_METADATA_VALUE#
info:eu-repo/grantAgreement/EC/H2020/676832
info:eu-repo/grantAgreement/EC/HE/701473
https://doi.org/10.1002/anie.202113519
No
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv Wiley-VCH
publisher.none.fl_str_mv Wiley-VCH
dc.source.none.fl_str_mv reponame:DIGITAL.CSIC. Repositorio Institucional del CSIC
instname:Consejo Superior de Investigaciones Científicas (CSIC)
instname_str Consejo Superior de Investigaciones Científicas (CSIC)
reponame_str DIGITAL.CSIC. Repositorio Institucional del CSIC
collection DIGITAL.CSIC. Repositorio Institucional del CSIC
repository.name.fl_str_mv
repository.mail.fl_str_mv
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