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Naphthoylhydrazones: coordination to metal ions and biological screening

2019-12Journal article Restricted
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dc.contributor.authorRibeiro, Nadia
dc.contributor.authorGalvao, Adelino M.
dc.contributor.authorGomes, Clara S. B.
dc.contributor.authorRamos, Helena
dc.contributor.authorPinheiro, Rute
dc.contributor.authorSaraiva, Lucilia
dc.contributor.authorNtungwe, Epole
dc.contributor.authorIsca, Vera
dc.contributor.authorRijo, Patricia
dc.contributor.authorCavaco, Isabel
dc.contributor.authorRamilo-Gomes, Filipa
dc.contributor.authorGuedes, Rita C.
dc.contributor.authorPessoa, Joao Costa
dc.contributor.authorCorreia, Isabel
dc.date.accessioned2020-07-24T10:50:44Z
dc.date.available2020-07-24T10:50:44Z
dc.date.issued2019-12
dc.description.abstractWe report the synthesis of 3-hydroxyl-2-naphthoylhydrazones containing pyrrole (HL1), furane (HL2) and thiophene (HL3) moieties and their V(IV)O-, Cu(II)- and Zn(II)-complexes. All compounds are characterized by the usual analytical techniques and coordination of the ligands to the metal ions is discussed based on spectroscopic data (FTIR, UV-vis, EPR and NMR) as well as CAMB3LYP DFT/TDDFT calculations, indicating the formation of neutral ML2 type complexes. The photophysical properties of ligands and complexes are disclosed. The binding to Bovine Serum Albumin (BSA) is evaluated in detail using several spectroscopic tools. Circular dichroism shows that the compounds, and particularly the ligand precursors, stabilize BSA, increasing its a-helical content. Fluorescence studies indicate the formation of 1 : 1 protein-compound adducts, which is corroborated by molecular docking studies that show the interaction between Trp 213 of BSA and the naphthalene rings. The general toxicity is evaluated using the Artemia salina lethality assay, with all compounds showing general toxicity towards the brine shrimp model. The cytotoxicity on human cancer cells (H1299, MCF7, and HCT116) is assessed for all compounds and the half-maximal inhibitory concentration (IC50) values are in the range from 0.57 to 27.35 mu M. Compounds containing L-1 (pyrrole derivative) are the most cytotoxic, with the vanadium and zinc complexes performing better than the copper ones, and some of them depicting IC50 values lower than 1.1 mM. However, selectivity needs improvement as the compounds show toxicity towards Artemia salina and normal fibroblasts.
dc.description.sponsorshipFundacao para a Ciencia e a Tecnologia (FCT)Portuguese Foundation for Science and Technology [UID/QUI/00100/2019, UID/MULTI/04349/2013, UID/BIO/04565/2013, RECI/QEQ-QIN/0189/2012, RECI/QEQ-MED/0330/2012, UID/DTP/04567/2016]
dc.description.sponsorshipPrograma Operacional Regional de Lisboa [LISBOA-01-0145-FEDER-007317]
dc.description.sponsorship[UID/04138/2019]
dc.description.sponsorship[SAICTPAC/0019/2015]
dc.description.sponsorship[PTDC/QUI-QAN/32242/2017]
dc.description.sponsorship[PD/BD/128320/2017]
dc.description.sponsorship[SFRH/BD/135797/2018]
dc.description.sponsorship[SFRH/BPD/107834/2015]
dc.description.sponsorship[UID/QUI/50006/2019]
dc.description.sponsorship[RECI/BBB-BEP/0124/2012]
dc.description.sponsorship[UID/DTP/04567/2019]
dc.description.sponsorship[SFRH/BD/119144/2016]
dc.description.versioninfo:eu-repo/semantics/publishedVersion
dc.identifier.doi10.1039/c9nj01816f
dc.identifier.issn1144-0546
dc.identifier.issn1369-9261
dc.identifier.urihttp://hdl.handle.net/10400.1/14147
dc.language.isoeng
dc.peerreviewedyes
dc.publisherRoyal Society of Chemistry
dc.subjectSchiff-base ligand
dc.subjectCopper(Ii) complexes
dc.subjectNickel(Ii) complexes
dc.subjectCrystal-structure
dc.subjectEukaryotic Dna
dc.subjectSerum-albumin
dc.subjectDonor Atoms
dc.subjectBinding
dc.subjectBovine
dc.subjectVanadium(Iv)
dc.titleNaphthoylhydrazones: coordination to metal ions and biological screening
dc.typejournal article
dspace.entity.typePublication
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/5876/UID%2FMulti%2F04349%2F2013/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/5876/UID%2FBIO%2F04565%2F2013/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/3599-PPCDT/RECI%2FQEQ-QIN%2F0189%2F2012/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/3599-PPCDT/RECI%2FQEQ-MED%2F0330%2F2012/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/3599-PPCDT/RECI%2FBBB-BEP%2F0124%2F2012/PT
oaire.citation.endPage17818
oaire.citation.issue45
oaire.citation.startPage17801
oaire.citation.titleNew Journal of Chemistry
oaire.citation.volume43
oaire.fundingStream5876
oaire.fundingStream5876
oaire.fundingStream3599-PPCDT
oaire.fundingStream3599-PPCDT
oaire.fundingStream3599-PPCDT
person.familyNamePALMA ANTUNES CAVACO
person.givenNameISABEL MARIA
person.identifierH-9087-2012
person.identifier.ciencia-idD515-FB5E-1205
person.identifier.orcid0000-0001-8651-9054
project.funder.identifierhttp://doi.org/10.13039/501100001871
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project.funder.nameFundação para a Ciência e a Tecnologia
project.funder.nameFundação para a Ciência e a Tecnologia
project.funder.nameFundação para a Ciência e a Tecnologia
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