Cu(II) and V(IV)O complexes with tri- or tetradentate ligands based on (2-hydroxybenzyl)- L-alanines reveal promising anticancer therapeutic potential
Autor(a) principal: | |
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Data de Publicação: | 2021 |
Outros Autores: | , , , , , , , , |
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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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 |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
format |
article |
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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metadata only access info:eu-repo/semantics/openAccess |
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metadata only access |
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openAccess |
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application/pdf |
dc.publisher.none.fl_str_mv |
Royal Society of Chemistry |
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Royal Society of Chemistry |
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