Chirality influence on the cytotoxic properties of anionic chiral bis(N-heterocyclic carbene)silver complexes

Complexes Na3[Ag(NHCR)2], 2a-e and 2b’-c’, where NHCR is a N-heterocyclic carbene of the 2,2′-(1H-2λ3,3λ4-imidazole-1,3-diyl)dicarboxylate type, were prepared by treatment of compounds HLR, 1a-e and 1b’-c’ (2-(1-(carboxyalkyl)-1H-imidazol-3-ium-3-yl)carboxylate), with silver oxide in the presence of...

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Autores: Carrasco Carrasco, Carlos Jesús, Montilla Ramos, Francisco Javier, Álvarez González, Eleuterio, Calderón Montaño, José Manuel, López Lázaro, Miguel, Galindo del Pozo, Agustín
Formato: artículo
Estado:Versión publicada
Fecha de publicación:2022
País:España
Recursos:Universidad de Sevilla (US)
Repositorio:idUS. Depósito de Investigación de la Universidad de Sevilla
OAI Identifier:oai:idus.us.es:11441/136581
Acesso em linha:https://hdl.handle.net/11441/136581
https://doi.org/10.1016/j.jinorgbio.2022.111924
Access Level:acceso abierto
Palavra-chave:Anticancer
Chiral
NHC-dicarboxylate
Silver
X-ray
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spelling Chirality influence on the cytotoxic properties of anionic chiral bis(N-heterocyclic carbene)silver complexesCarrasco Carrasco, Carlos JesúsMontilla Ramos, Francisco JavierÁlvarez González, EleuterioCalderón Montaño, José ManuelLópez Lázaro, MiguelGalindo del Pozo, AgustínAnticancerChiralNHC-dicarboxylateSilverX-rayComplexes Na3[Ag(NHCR)2], 2a-e and 2b’-c’, where NHCR is a N-heterocyclic carbene of the 2,2′-(1H-2λ3,3λ4-imidazole-1,3-diyl)dicarboxylate type, were prepared by treatment of compounds HLR, 1a-e and 1b’-c’ (2-(1-(carboxyalkyl)-1H-imidazol-3-ium-3-yl)carboxylate), with silver oxide in the presence of aqueous sodium hydroxide. They were characterized by analytical, spectroscopic (infrared, IR, 1H and 13C nuclear magnetic resonance, NMR, and circular dichroism) and X-ray methods (2a). In the solid state, the anionic part of complex 2a, [Ag(NHCH)2]3−, shows a linear disposition of Ccarbene-Ag-Ccarbene atoms and an eclipsed conformation of the two NHC ligands. The proposed bis(NHC) nature of the silver complexes was maintained in solution according to NMR and density functional theory (DFT) calculations. The cytotoxic activity of compounds 2 was evaluated against four cancer cell lines and one non-cancerous cell line and several structure-activity correlations were found for these complexes. For instance, the activity decreased when the bulkiness of the R alkyl group in Na3[Ag(NHCR)2] increased. More interesting is the detected chirality-anticancer relationship, where complexes Na3[Ag{(S,S)-NHCR}2] (R = Me, 2b; iPr, 2c) showed better anticancer activity than those of their enantiomeric derivatives Na3[Ag{(R,R)-NHCR}2] (R = Me, 2b’; iPr, 2c’).Ministerio de Ciencia e Innovación PGC2018-093443-B-I00Universidad de Sevilla VIPPIT-2021-I.5Premio Mensual Publicación Científica Destacada de la US. Facultad de QuímicaElsevierQuímica InorgánicaFarmacologíaMinisterio de Ciencia e Innovación (MICIN). EspañaUniversidad de Sevilla2022info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionapplication/pdfapplication/pdfhttps://hdl.handle.net/11441/136581https://doi.org/10.1016/j.jinorgbio.2022.111924reponame:idUS. Depósito de Investigación de la Universidad de Sevillainstname:Universidad de Sevilla (US)InglésJournal of Inorganic Biochemistry, 235, 111924.PGC2018-093443-B-I00VIPPIT-2021-I.5https://doi.org/10.1016/j.jinorgbio.2022.111924info:eu-repo/semantics/openAccessoai:idus.us.es:11441/1365812026-06-17T12:51:07Z
dc.title.none.fl_str_mv Chirality influence on the cytotoxic properties of anionic chiral bis(N-heterocyclic carbene)silver complexes
title Chirality influence on the cytotoxic properties of anionic chiral bis(N-heterocyclic carbene)silver complexes
spellingShingle Chirality influence on the cytotoxic properties of anionic chiral bis(N-heterocyclic carbene)silver complexes
Carrasco Carrasco, Carlos Jesús
Anticancer
Chiral
NHC-dicarboxylate
Silver
X-ray
title_short Chirality influence on the cytotoxic properties of anionic chiral bis(N-heterocyclic carbene)silver complexes
title_full Chirality influence on the cytotoxic properties of anionic chiral bis(N-heterocyclic carbene)silver complexes
title_fullStr Chirality influence on the cytotoxic properties of anionic chiral bis(N-heterocyclic carbene)silver complexes
title_full_unstemmed Chirality influence on the cytotoxic properties of anionic chiral bis(N-heterocyclic carbene)silver complexes
title_sort Chirality influence on the cytotoxic properties of anionic chiral bis(N-heterocyclic carbene)silver complexes
dc.creator.none.fl_str_mv Carrasco Carrasco, Carlos Jesús
Montilla Ramos, Francisco Javier
Álvarez González, Eleuterio
Calderón Montaño, José Manuel
López Lázaro, Miguel
Galindo del Pozo, Agustín
author Carrasco Carrasco, Carlos Jesús
author_facet Carrasco Carrasco, Carlos Jesús
Montilla Ramos, Francisco Javier
Álvarez González, Eleuterio
Calderón Montaño, José Manuel
López Lázaro, Miguel
Galindo del Pozo, Agustín
author_role author
author2 Montilla Ramos, Francisco Javier
Álvarez González, Eleuterio
Calderón Montaño, José Manuel
López Lázaro, Miguel
Galindo del Pozo, Agustín
author2_role author
author
author
author
author
dc.contributor.none.fl_str_mv Química Inorgánica
Farmacología
Ministerio de Ciencia e Innovación (MICIN). España
Universidad de Sevilla
dc.subject.none.fl_str_mv Anticancer
Chiral
NHC-dicarboxylate
Silver
X-ray
topic Anticancer
Chiral
NHC-dicarboxylate
Silver
X-ray
description Complexes Na3[Ag(NHCR)2], 2a-e and 2b’-c’, where NHCR is a N-heterocyclic carbene of the 2,2′-(1H-2λ3,3λ4-imidazole-1,3-diyl)dicarboxylate type, were prepared by treatment of compounds HLR, 1a-e and 1b’-c’ (2-(1-(carboxyalkyl)-1H-imidazol-3-ium-3-yl)carboxylate), with silver oxide in the presence of aqueous sodium hydroxide. They were characterized by analytical, spectroscopic (infrared, IR, 1H and 13C nuclear magnetic resonance, NMR, and circular dichroism) and X-ray methods (2a). In the solid state, the anionic part of complex 2a, [Ag(NHCH)2]3−, shows a linear disposition of Ccarbene-Ag-Ccarbene atoms and an eclipsed conformation of the two NHC ligands. The proposed bis(NHC) nature of the silver complexes was maintained in solution according to NMR and density functional theory (DFT) calculations. The cytotoxic activity of compounds 2 was evaluated against four cancer cell lines and one non-cancerous cell line and several structure-activity correlations were found for these complexes. For instance, the activity decreased when the bulkiness of the R alkyl group in Na3[Ag(NHCR)2] increased. More interesting is the detected chirality-anticancer relationship, where complexes Na3[Ag{(S,S)-NHCR}2] (R = Me, 2b; iPr, 2c) showed better anticancer activity than those of their enantiomeric derivatives Na3[Ag{(R,R)-NHCR}2] (R = Me, 2b’; iPr, 2c’).
publishDate 2022
dc.date.none.fl_str_mv 2022
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv https://hdl.handle.net/11441/136581
https://doi.org/10.1016/j.jinorgbio.2022.111924
url https://hdl.handle.net/11441/136581
https://doi.org/10.1016/j.jinorgbio.2022.111924
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv Journal of Inorganic Biochemistry, 235, 111924.
PGC2018-093443-B-I00
VIPPIT-2021-I.5
https://doi.org/10.1016/j.jinorgbio.2022.111924
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Elsevier
publisher.none.fl_str_mv Elsevier
dc.source.none.fl_str_mv reponame:idUS. Depósito de Investigación de la Universidad de Sevilla
instname:Universidad de Sevilla (US)
instname_str Universidad de Sevilla (US)
reponame_str idUS. Depósito de Investigación de la Universidad de Sevilla
collection idUS. Depósito de Investigación de la Universidad de Sevilla
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,198674

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