Antimicrobial and antitumor activity of S-methyl dithiocarbazate Schiff base zinc(II) complexes
Autor(a) principal: | |
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Data de Publicação: | 2021 |
Outros Autores: | , , , , , , , , , , , , , , |
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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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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1808129347020652544 |