Cu(II) and V(IV)O complexes with tri- or tetradentate ligands based on (2-hydroxybenzyl)- L-alanines reveal promising anticancer therapeutic potential

Detalhes bibliográficos
Autor(a) principal: Ribeiro, Nádia
Data de Publicação: 2021
Outros Autores: Bulut, İpek, Cevatemre, Buse, Teixeira, Carlos, Yildizhan, Yasemin, André, Vânia, Adão, Pedro, Pessoa, João, Acilan, Ceyda, Correia, Isabel
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/10400.8/6067
Resumo: Acknowledgements : The authors thank the financial support from Fundação para a Ciência e Tecnologia (FCT) through project UIDB/00100/2020. N. Ribeiro acknowledges FCT for SFRH/BD/135797/2018 grant. C. Teixeira and P. Adão acknowledge grants SFRH/BPD/79778/2011, BL/CQE-2014-001 and PD/BD/106078/2015. Isabel Correia thanks program FCT Investigator (IF/00841/2012). P. Adão also acknowledges the MARE - Centro de Ciências do Mar e do Ambiente, Politécnico de Leiria, which is financed by national funds from FCT (UID/MAR/04292/2019, UIDB/04292/2020) and the project “SmartBioR- Smart Valorization of Endogenous Marine Biological Resources Under a Changing Climate” (Centro-01-0145-FEDER-000018) co-funded by Centro 2020, Portugal 2020 and European Regional Development Fund (FEDER). The Portuguese NMR and Mass spectrometry IST-UL are acknowledged for the access to the equipment. This work was supported by Koç University School of Medicine (KUSOM) and the authors gratefully acknowledge use of the services and facilities of the Koç University Research Center for Translational Medicine (KUTTAM), funded by the Presidency of Turkey, Presidency of Strategy and Budget. The content is solely the responsibility of the authors and does not necessarily represent the official views of the Presidency of Strategy and Budget
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spelling Cu(II) and V(IV)O complexes with tri- or tetradentate ligands based on (2-hydroxybenzyl)- L-alanines reveal promising anticancer therapeutic potentialAcknowledgements : The authors thank the financial support from Fundação para a Ciência e Tecnologia (FCT) through project UIDB/00100/2020. N. Ribeiro acknowledges FCT for SFRH/BD/135797/2018 grant. C. Teixeira and P. Adão acknowledge grants SFRH/BPD/79778/2011, BL/CQE-2014-001 and PD/BD/106078/2015. Isabel Correia thanks program FCT Investigator (IF/00841/2012). P. Adão also acknowledges the MARE - Centro de Ciências do Mar e do Ambiente, Politécnico de Leiria, which is financed by national funds from FCT (UID/MAR/04292/2019, UIDB/04292/2020) and the project “SmartBioR- Smart Valorization of Endogenous Marine Biological Resources Under a Changing Climate” (Centro-01-0145-FEDER-000018) co-funded by Centro 2020, Portugal 2020 and European Regional Development Fund (FEDER). The Portuguese NMR and Mass spectrometry IST-UL are acknowledged for the access to the equipment. This work was supported by Koç University School of Medicine (KUSOM) and the authors gratefully acknowledge use of the services and facilities of the Koç University Research Center for Translational Medicine (KUTTAM), funded by the Presidency of Turkey, Presidency of Strategy and Budget. The content is solely the responsibility of the authors and does not necessarily represent the official views of the Presidency of Strategy and BudgetFour new ligand precursors (H2L1–H2L4), derived from the Mannich condensation of two amino acids (L-Val and L-Phe) and two 3,5-disubstituted phenols (t-Bu or Me), and the corresponding oxidovanadium(IV) (1–4) and copper(II) (6–7) complexes are synthesized. Two other related compounds (H2L5 and H2L6), containing an additional 2-methyl-pyridine arm, and the corresponding VIVO (5) and CuII (8–9) complexes were also obtained. All metal complexes are monomeric in the solid state, having a solvent molecule or a chloride ion in the coordination sphere. The in vitro cytotoxic activity of all compounds is evaluated against cancer cells from different origins. The IC50 values at 72 h are in the range of 6–15 μM for HeLa cells, 4–17 μM for A-549 cells and >25 μM for MDA-MB-231 cells, except for [VIVOL1(CH3OH)] (1) and [CuL6(H2O)] (9). With the exception of H2L6, overall, the metal complexes are more cytotoxic than the corresponding ligand precursors. Globally, the cellular viability data show that (i) the L-Phe derived compounds are more cytotoxic than the corresponding L-Val complexes; (ii) the presence of the bulkier t-Bu groups increases the cytotoxicity; (iii) the presence of a 2-methyl pyridine arm increases considerably the cytotoxicity; and (iv) the CuII-complexes are more cytotoxic than the VIVO-compounds. Complexes [VIVOL3(CH3OH)] (3), [CuL3(H2O)] (7) and [CuL5(H2O)] (8) were further evaluated and their mechanism of action was determined to be apoptosis, evidenced by AnnexinV staining and the increase in caspase 3/7 activity. Compounds 3, 7 and 8 also exhibit DNA cleavage activity, involving the formation of reactive oxygen species and were able to induce genomic damage in cells as determined by COMET assay.Royal Society of ChemistryIC-OnlineRibeiro, NádiaBulut, İpekCevatemre, BuseTeixeira, CarlosYildizhan, YaseminAndré, VâniaAdão, PedroPessoa, JoãoAcilan, CeydaCorreia, Isabel2021-08-10T17:26:36Z20212021-01-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10400.8/6067engRibeiro, N., Bulut, I., Cevatemre, B., Teixeira, C., Yildizhan, Y., André, V., Adão, P., Pessoa, J.C., Acilan, C. & Correia, I. (2021). Cu(II) and V(IV)O complexes with tri- or tetradentate ligands based on (2-hydroxybenzyl)- L-alanines reveal promising anticancer therapeutic potential. Dalton Trans.2021, 50, 157-169. https://doi.org/10.1039/d0dt03331f1477-922610.1039/d0dt03331fmetadata only accessinfo:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2024-01-17T15:52:18Zoai:iconline.ipleiria.pt:10400.8/6067Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-20T01:49:23.798393Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãofalse
dc.title.none.fl_str_mv Cu(II) and V(IV)O complexes with tri- or tetradentate ligands based on (2-hydroxybenzyl)- L-alanines reveal promising anticancer therapeutic potential
title Cu(II) and V(IV)O complexes with tri- or tetradentate ligands based on (2-hydroxybenzyl)- L-alanines reveal promising anticancer therapeutic potential
spellingShingle Cu(II) and V(IV)O complexes with tri- or tetradentate ligands based on (2-hydroxybenzyl)- L-alanines reveal promising anticancer therapeutic potential
Ribeiro, Nádia
title_short Cu(II) and V(IV)O complexes with tri- or tetradentate ligands based on (2-hydroxybenzyl)- L-alanines reveal promising anticancer therapeutic potential
title_full Cu(II) and V(IV)O complexes with tri- or tetradentate ligands based on (2-hydroxybenzyl)- L-alanines reveal promising anticancer therapeutic potential
title_fullStr Cu(II) and V(IV)O complexes with tri- or tetradentate ligands based on (2-hydroxybenzyl)- L-alanines reveal promising anticancer therapeutic potential
title_full_unstemmed Cu(II) and V(IV)O complexes with tri- or tetradentate ligands based on (2-hydroxybenzyl)- L-alanines reveal promising anticancer therapeutic potential
title_sort Cu(II) and V(IV)O complexes with tri- or tetradentate ligands based on (2-hydroxybenzyl)- L-alanines reveal promising anticancer therapeutic potential
author Ribeiro, Nádia
author_facet Ribeiro, Nádia
Bulut, İpek
Cevatemre, Buse
Teixeira, Carlos
Yildizhan, Yasemin
André, Vânia
Adão, Pedro
Pessoa, João
Acilan, Ceyda
Correia, Isabel
author_role author
author2 Bulut, İpek
Cevatemre, Buse
Teixeira, Carlos
Yildizhan, Yasemin
André, Vânia
Adão, Pedro
Pessoa, João
Acilan, Ceyda
Correia, Isabel
author2_role author
author
author
author
author
author
author
author
author
dc.contributor.none.fl_str_mv IC-Online
dc.contributor.author.fl_str_mv Ribeiro, Nádia
Bulut, İpek
Cevatemre, Buse
Teixeira, Carlos
Yildizhan, Yasemin
André, Vânia
Adão, Pedro
Pessoa, João
Acilan, Ceyda
Correia, Isabel
description Acknowledgements : The authors thank the financial support from Fundação para a Ciência e Tecnologia (FCT) through project UIDB/00100/2020. N. Ribeiro acknowledges FCT for SFRH/BD/135797/2018 grant. C. Teixeira and P. Adão acknowledge grants SFRH/BPD/79778/2011, BL/CQE-2014-001 and PD/BD/106078/2015. Isabel Correia thanks program FCT Investigator (IF/00841/2012). P. Adão also acknowledges the MARE - Centro de Ciências do Mar e do Ambiente, Politécnico de Leiria, which is financed by national funds from FCT (UID/MAR/04292/2019, UIDB/04292/2020) and the project “SmartBioR- Smart Valorization of Endogenous Marine Biological Resources Under a Changing Climate” (Centro-01-0145-FEDER-000018) co-funded by Centro 2020, Portugal 2020 and European Regional Development Fund (FEDER). The Portuguese NMR and Mass spectrometry IST-UL are acknowledged for the access to the equipment. This work was supported by Koç University School of Medicine (KUSOM) and the authors gratefully acknowledge use of the services and facilities of the Koç University Research Center for Translational Medicine (KUTTAM), funded by the Presidency of Turkey, Presidency of Strategy and Budget. The content is solely the responsibility of the authors and does not necessarily represent the official views of the Presidency of Strategy and Budget
publishDate 2021
dc.date.none.fl_str_mv 2021-08-10T17:26:36Z
2021
2021-01-01T00:00:00Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
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status_str publishedVersion
dc.identifier.uri.fl_str_mv http://hdl.handle.net/10400.8/6067
url http://hdl.handle.net/10400.8/6067
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv Ribeiro, N., Bulut, I., Cevatemre, B., Teixeira, C., Yildizhan, Y., André, V., Adão, P., Pessoa, J.C., Acilan, C. & Correia, I. (2021). Cu(II) and V(IV)O complexes with tri- or tetradentate ligands based on (2-hydroxybenzyl)- L-alanines reveal promising anticancer therapeutic potential. Dalton Trans.2021, 50, 157-169. https://doi.org/10.1039/d0dt03331f
1477-9226
10.1039/d0dt03331f
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dc.publisher.none.fl_str_mv Royal Society of Chemistry
publisher.none.fl_str_mv Royal Society of Chemistry
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