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Antimicrobial and antitumor activity of S-methyl dithiocarbazate Schiff base zinc(II) complexes

2021Journal article Restricted access
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dc.contributor.authorRamilo-Gomes, Filipa
dc.contributor.authorAlemu, Yemataw
dc.contributor.authorTekamo, Israel
dc.contributor.authorCavaco, Isabel
dc.contributor.authorCampos, Débora L.
dc.contributor.authorPavan, Fernando R.
dc.contributor.authorGomes, Clara S.B.
dc.contributor.authorBrito, Vanessa
dc.contributor.authorSantos, Adriana O.
dc.contributor.authorDomingues, Fernanda
dc.contributor.authorLuís, Ângelo
dc.contributor.authorMarques, M. Matilde
dc.contributor.authorPessoa, João Costa
dc.contributor.authorFerreira, Susana
dc.contributor.authorSilvestre, Samuel
dc.contributor.authorCorreia, Isabel
dc.date.accessioned2021-07-19T08:45:44Z
dc.date.available2021-07-19T08:45:44Z
dc.date.issued2021
dc.description.abstractSchiff bases (SB) obtained from S-methyl dithiocarbazate and aromatic aldehydes: salicylaldehyde (H2L1), o-vanillin (H2L2), pyridoxal (H2L3) and 2,6-diformyl-4-methylphenol (H3L4), and their corresponding Zn(II)-complexes (1-4), are synthesized. All compounds are characterized by elemental analyses, infrared, UV-Vis, nuclear magnetic resonance spectroscopy and mass spectrometry. The structures of H2L2 and [Zn2(L1)2(H2O)(DMF)] (1a) (DMF = dimethylformamide) are solved by single crystal X-ray diffraction. The SB coordinates the metal center through the Ophenolate, Nimine and Sthiolate atoms. The radical scavenging activity is tested using the 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay, with all ligand precursors showing IC50 values ~40 μM. Cytotoxicity studies with several tumor cell lines (PC-3, MCF-7 and Caco-2) as well as a non-tumoral cell line (NHDF) are reported. Interestingly, 1 has relevant and selective antiproliferative effect against Caco-2 cells (IC50 = 9.1 μM). Their antimicrobial activity is evaluated in five bacterial strains (Klebsiella pneumoniae, Acinetobacter baumannii, Listeria monocytogenes, Pseudomonas aeruginosa and Staphylococcus aureus) and two yeast strains (Candida albicans and Candida tropicalis) with some compounds showing bacteriostatic and fungicidal activity. The minimal inhibitory concentration (MIC90) of HnL against Mycobacterium tuberculosis is also reported, with H2L2 and H3L4 showing very high activity (MIC90 < 0.6 μg/mL). The ability of the compounds to bind bovine serum albumin (BSA) and DNA is evaluated for H3L4 and [Zn2(L4)(CH3COO)] (4), both showing high binding constants to BSA (ca. 106 M-1) and ability to bind DNA. Overall, the reported compounds show relevant antitumor and antimicrobial properties, our data indicating they may be promising compounds in several fields of medicinal chemistry.pt_PT
dc.description.sponsorshipFCT (projects UIDB/00100/2020, UIDP/00100/2020, PTDC/QUI-QAN/32242/2017, UID/Multi/00709/2019, UIDB/50006/2020, UIDB/04378/2020 , SAICTPAC/0019/2015; PD/BD/128320/2017), Programa Operacional Regional de Lisboa (LISBOA-01-0145-FEDER-007317) e FEDER POCI-COMPETE 2020-Operational Programme Competitiveness and Internationalisation (Project POCI-01-0145-FEDER-007491). Yemataw Addis and Israel Tekamo thank the Erasmus Mundus program.pt_PT
dc.description.versioninfo:eu-repo/semantics/publishedVersionpt_PT
dc.identifier.doi10.1016/j.jinorgbio.2020.111331pt_PT
dc.identifier.issn0162-0134
dc.identifier.urihttp://hdl.handle.net/10400.1/16782
dc.language.isoengpt_PT
dc.peerreviewedyespt_PT
dc.publisherElsevierpt_PT
dc.subjectSchiff basesZn(II) complexespt_PT
dc.subjectS-methyl dithiocarbazatept_PT
dc.subjectAnticancerpt_PT
dc.subjectAntimicrobialpt_PT
dc.subjectDNApt_PT
dc.titleAntimicrobial and antitumor activity of S-methyl dithiocarbazate Schiff base zinc(II) complexespt_PT
dc.typejournal article
dspace.entity.typePublication
oaire.citation.startPage111331pt_PT
oaire.citation.titleJournal of Inorganic Biochemistrypt_PT
oaire.citation.volume216pt_PT
person.familyNameAlemu
person.familyNamePALMA ANTUNES CAVACO
person.givenNameYemataw
person.givenNameISABEL MARIA
person.identifierH-9087-2012
person.identifier.ciencia-idD515-FB5E-1205
person.identifier.orcid0000-0002-8062-6139
person.identifier.orcid0000-0001-8651-9054
rcaap.rightsrestrictedAccesspt_PT
rcaap.typearticlept_PT
relation.isAuthorOfPublication78de820c-0d5e-42a1-8591-23af251fa128
relation.isAuthorOfPublicationb499959b-bea5-4292-bdb2-4311b0aa82de
relation.isAuthorOfPublication.latestForDiscovery78de820c-0d5e-42a1-8591-23af251fa128

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