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

Detalhes bibliográficos
Autor(a) principal: Ramilo-Gomes, Filipa
Data de Publicação: 2021
Outros Autores: Addis, Yemataw, Tekamo, Israel, Cavaco, Isabel, Campos, Débora L. [UNESP], Pavan, Fernando R. [UNESP], Gomes, Clara S.B., Brito, Vanessa, Santos, Adriana O., Domingues, Fernanda, Luís, Ângelo, Marques, M. Matilde, Pessoa, João Costa, Ferreira, Susana, Silvestre, Samuel, Correia, Isabel
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Institucional da UNESP
Texto Completo: http://dx.doi.org/10.1016/j.jinorgbio.2020.111331
http://hdl.handle.net/11449/208276
Resumo: Schiff 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.
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spelling Antimicrobial and antitumor activity of S-methyl dithiocarbazate Schiff base zinc(II) complexesAnticancerAntimicrobialDNAS-methyl dithiocarbazateSchiff basesZn(II) complexesSchiff 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.Centro de Química Estrutural and Departamento de Engenharia Química Instituto Superior Técnico Universidade de Lisboa, Av. Rovisco PaisInstituto de Investigação do Medicamento (iMed.ULisboa) Faculdade de Farmácia Universidade de Lisboa, Av. Professor Gama PintoDepartamento de Química e Farmácia Universidade do Algarve, Campus de GambelasFaculdade de Ciências Farmacêuticas UNESP, C.P.582LAQV-REQUIMTE – Laboratório Associado para a Química Verde Departamento de Química Faculdade de Ciências e Tecnologia Universidade NOVA de LisboaApplied Molecular Biosciences Unit – UCIBIO Faculdade de Ciências e Tecnologia Universidade NOVA de LisboaCICS-UBI - Health Sciences Research Centre University of Beira Interior, Av. Infante D. HenriqueFaculdade de Ciências Farmacêuticas UNESP, C.P.582Universidade de LisboaUniversidade do AlgarveUniversidade Estadual Paulista (Unesp)Universidade NOVA de LisboaUniversity of Beira InteriorRamilo-Gomes, FilipaAddis, YematawTekamo, IsraelCavaco, IsabelCampos, Débora L. [UNESP]Pavan, Fernando R. [UNESP]Gomes, Clara S.B.Brito, VanessaSantos, Adriana O.Domingues, FernandaLuís, ÂngeloMarques, M. MatildePessoa, João CostaFerreira, SusanaSilvestre, SamuelCorreia, Isabel2021-06-25T11:09:35Z2021-06-25T11:09:35Z2021-03-01info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articlehttp://dx.doi.org/10.1016/j.jinorgbio.2020.111331Journal of Inorganic Biochemistry, v. 216.1873-33440162-0134http://hdl.handle.net/11449/20827610.1016/j.jinorgbio.2020.1113312-s2.0-85098467869Scopusreponame:Repositório Institucional da UNESPinstname:Universidade Estadual Paulista (UNESP)instacron:UNESPengJournal of Inorganic Biochemistryinfo:eu-repo/semantics/openAccess2024-06-24T13:08:13Zoai:repositorio.unesp.br:11449/208276Repositório InstitucionalPUBhttp://repositorio.unesp.br/oai/requestopendoar:29462024-08-05T21:41:27.401718Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP)false
dc.title.none.fl_str_mv Antimicrobial and antitumor activity of S-methyl dithiocarbazate Schiff base zinc(II) complexes
title Antimicrobial and antitumor activity of S-methyl dithiocarbazate Schiff base zinc(II) complexes
spellingShingle Antimicrobial and antitumor activity of S-methyl dithiocarbazate Schiff base zinc(II) complexes
Ramilo-Gomes, Filipa
Anticancer
Antimicrobial
DNA
S-methyl dithiocarbazate
Schiff bases
Zn(II) complexes
title_short Antimicrobial and antitumor activity of S-methyl dithiocarbazate Schiff base zinc(II) complexes
title_full Antimicrobial and antitumor activity of S-methyl dithiocarbazate Schiff base zinc(II) complexes
title_fullStr Antimicrobial and antitumor activity of S-methyl dithiocarbazate Schiff base zinc(II) complexes
title_full_unstemmed Antimicrobial and antitumor activity of S-methyl dithiocarbazate Schiff base zinc(II) complexes
title_sort Antimicrobial and antitumor activity of S-methyl dithiocarbazate Schiff base zinc(II) complexes
author Ramilo-Gomes, Filipa
author_facet Ramilo-Gomes, Filipa
Addis, Yemataw
Tekamo, Israel
Cavaco, Isabel
Campos, Débora L. [UNESP]
Pavan, Fernando R. [UNESP]
Gomes, Clara S.B.
Brito, Vanessa
Santos, Adriana O.
Domingues, Fernanda
Luís, Ângelo
Marques, M. Matilde
Pessoa, João Costa
Ferreira, Susana
Silvestre, Samuel
Correia, Isabel
author_role author
author2 Addis, Yemataw
Tekamo, Israel
Cavaco, Isabel
Campos, Débora L. [UNESP]
Pavan, Fernando R. [UNESP]
Gomes, Clara S.B.
Brito, Vanessa
Santos, Adriana O.
Domingues, Fernanda
Luís, Ângelo
Marques, M. Matilde
Pessoa, João Costa
Ferreira, Susana
Silvestre, Samuel
Correia, Isabel
author2_role author
author
author
author
author
author
author
author
author
author
author
author
author
author
author
dc.contributor.none.fl_str_mv Universidade de Lisboa
Universidade do Algarve
Universidade Estadual Paulista (Unesp)
Universidade NOVA de Lisboa
University of Beira Interior
dc.contributor.author.fl_str_mv Ramilo-Gomes, Filipa
Addis, Yemataw
Tekamo, Israel
Cavaco, Isabel
Campos, Débora L. [UNESP]
Pavan, Fernando R. [UNESP]
Gomes, Clara S.B.
Brito, Vanessa
Santos, Adriana O.
Domingues, Fernanda
Luís, Ângelo
Marques, M. Matilde
Pessoa, João Costa
Ferreira, Susana
Silvestre, Samuel
Correia, Isabel
dc.subject.por.fl_str_mv Anticancer
Antimicrobial
DNA
S-methyl dithiocarbazate
Schiff bases
Zn(II) complexes
topic Anticancer
Antimicrobial
DNA
S-methyl dithiocarbazate
Schiff bases
Zn(II) complexes
description Schiff 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.
publishDate 2021
dc.date.none.fl_str_mv 2021-06-25T11:09:35Z
2021-06-25T11:09:35Z
2021-03-01
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://dx.doi.org/10.1016/j.jinorgbio.2020.111331
Journal of Inorganic Biochemistry, v. 216.
1873-3344
0162-0134
http://hdl.handle.net/11449/208276
10.1016/j.jinorgbio.2020.111331
2-s2.0-85098467869
url http://dx.doi.org/10.1016/j.jinorgbio.2020.111331
http://hdl.handle.net/11449/208276
identifier_str_mv Journal of Inorganic Biochemistry, v. 216.
1873-3344
0162-0134
10.1016/j.jinorgbio.2020.111331
2-s2.0-85098467869
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv Journal of Inorganic Biochemistry
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.source.none.fl_str_mv Scopus
reponame:Repositório Institucional da UNESP
instname:Universidade Estadual Paulista (UNESP)
instacron:UNESP
instname_str Universidade Estadual Paulista (UNESP)
instacron_str UNESP
institution UNESP
reponame_str Repositório Institucional da UNESP
collection Repositório Institucional da UNESP
repository.name.fl_str_mv Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP)
repository.mail.fl_str_mv
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