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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 potential

2021Journal article Restricted access
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dc.contributor.authorRibeiro, Nádia
dc.contributor.authorBulut, İpek
dc.contributor.authorCevatemre, Buse
dc.contributor.authorTeixeira, Carlos
dc.contributor.authorYildizhan, Yasemin
dc.contributor.authorAndré, Vânia
dc.contributor.authorAdão, Pedro
dc.contributor.authorPessoa, João
dc.contributor.authorAcilan, Ceyda
dc.contributor.authorCorreia, Isabel
dc.date.accessioned2021-08-10T17:26:36Z
dc.date.available2021-08-10T17:26:36Z
dc.date.issued2021
dc.descriptionAcknowledgements : 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
dc.description.abstractFour 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.pt_PT
dc.description.versioninfo:eu-repo/semantics/publishedVersionpt_PT
dc.identifier.citationRibeiro, 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/d0dt03331fpt_PT
dc.identifier.doi10.1039/d0dt03331fpt_PT
dc.identifier.issn1477-9226
dc.identifier.issn1477-9234
dc.identifier.urihttp://hdl.handle.net/10400.8/6067
dc.language.isoengpt_PT
dc.peerreviewedyespt_PT
dc.publisherRoyal Society of Chemistrypt_PT
dc.relationNew 8-hydroxyquinoline metallodrugs: synthesis, speciation and uptake
dc.relationDEVELOPMENT OF NEW RECYCLABLE AND WIDELY APPLICABLE HETEROGENEOUS CATALYSTS FOR CATALYTIC OXIDATIONS AND REDUCTIONS
dc.relationAminoacid-derived transition metal complexes as C-C bond forming and C-H activation catalysts
dc.relationInteraction of biomacromolecules with ionic liquids
dc.relationMARE - Marine and Environmental Sciences Centre
dc.relationMarine and Environmental Sciences Centre
dc.relation.publisherversionhttps://pubs.rsc.org/en/content/articlelanding/2021/DT/D0DT03331Fpt_PT
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/pt_PT
dc.titleCu(II) and V(IV)O complexes with tri- or tetradentate ligands based on (2-hydroxybenzyl)- L-alanines reveal promising anticancer therapeutic potentialpt_PT
dc.typejournal article
dspace.entity.typePublication
oaire.awardTitleNew 8-hydroxyquinoline metallodrugs: synthesis, speciation and uptake
oaire.awardTitleDEVELOPMENT OF NEW RECYCLABLE AND WIDELY APPLICABLE HETEROGENEOUS CATALYSTS FOR CATALYTIC OXIDATIONS AND REDUCTIONS
oaire.awardTitleAminoacid-derived transition metal complexes as C-C bond forming and C-H activation catalysts
oaire.awardTitleInteraction of biomacromolecules with ionic liquids
oaire.awardTitleMARE - Marine and Environmental Sciences Centre
oaire.awardTitleMarine and Environmental Sciences Centre
oaire.awardURIinfo:eu-repo/grantAgreement/FCT//SFRH%2FBD%2F135797%2F2018/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT//SFRH%2FBPD%2F79778%2F2011/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT//PD%2FBD%2F106078%2F2015/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/Investigador FCT/IF%2F00841%2F2012%2FCP0171%2FCT0009/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UID%2FMAR%2F04292%2F2019/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDB%2F04292%2F2020/PT
oaire.citation.endPage169pt_PT
oaire.citation.issue1pt_PT
oaire.citation.startPage157pt_PT
oaire.citation.titleDalton Transactionspt_PT
oaire.citation.volume50pt_PT
oaire.fundingStreamInvestigador FCT
oaire.fundingStream6817 - DCRRNI ID
oaire.fundingStream6817 - DCRRNI ID
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