Dithiocarbazate ligands and their Ni(II) complexes with potential biological activity : structural, antitumor and molecular docking study
Autor(a) principal: | |
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Data de Publicação: | 2023 |
Outros Autores: | , , , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Institucional da UnB |
Texto Completo: | http://repositorio2.unb.br/jspui/handle/10482/46638 https://doi.org/10.3389/fmolb.2023.1146820 |
Resumo: | n the search for new metal complexes with antitumor potential, two dithiocarbazate ligands derived from 1,1,1-trifluoro-2,4-pentanedione (H 2 L 1) and (H2 L2 ) and four Ni(II) complexes, [Ni(L 1 )PPh3 ] (1), [Ni(L 1)Py] (2), [Ni(L2)PPh 3](3), and [Ni(L 2 )Py] (4), were successfully synthesized and investigated by physical-chemistry and spectroscopic methods. The crystal structure of the H2 L 1 and the Ni(II) complexes has been elucidated by single-crystal X-ray diffraction. The obtained structure from H 2 L 1 confirms the cyclization reaction and formation of the pyrazoline derivative. The results showed square planar geometry to the metal centers, in which dithiocarbazates coordinated by the ONS donor system and a triphenylphosphine or pyridine molecule complete the coordination sphere. Hirshfeld surface analysis by dnorm function was investigated and showed π–π stacking interactions upon the molecular packing of H 2 L1 and non-classical hydrogen bonds for all compounds. Fingerprint plots showed the main interactions attributed to H·H C·H, O·H, Br·H, and F·H, with contacts contributing between 1.9% and 38.2%. The mass spectrometry data indicated the presence of molecular ions [M + H] + and characteristic fragmentations of the compounds, which indicated the same behavior of the compounds in solution and solid state. Molecular docking simulations were studied to evaluate the properties and interactions of the free dithiocarbazates and their Ni(II) complexes with selected proteins and DNA. These results were supported by in vitro cytotoxicity assays against four cancer cell lines, showing that the synthesized metal complexes display promising biological activity. |
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Dithiocarbazate ligands and their Ni(II) complexes with potential biological activity : structural, antitumor and molecular docking studyComplexos de níquel (II)DitiocarbazatosEspectrometria de massaSuperfície de HirshfeldAtividade antitumoraln the search for new metal complexes with antitumor potential, two dithiocarbazate ligands derived from 1,1,1-trifluoro-2,4-pentanedione (H 2 L 1) and (H2 L2 ) and four Ni(II) complexes, [Ni(L 1 )PPh3 ] (1), [Ni(L 1)Py] (2), [Ni(L2)PPh 3](3), and [Ni(L 2 )Py] (4), were successfully synthesized and investigated by physical-chemistry and spectroscopic methods. The crystal structure of the H2 L 1 and the Ni(II) complexes has been elucidated by single-crystal X-ray diffraction. The obtained structure from H 2 L 1 confirms the cyclization reaction and formation of the pyrazoline derivative. The results showed square planar geometry to the metal centers, in which dithiocarbazates coordinated by the ONS donor system and a triphenylphosphine or pyridine molecule complete the coordination sphere. Hirshfeld surface analysis by dnorm function was investigated and showed π–π stacking interactions upon the molecular packing of H 2 L1 and non-classical hydrogen bonds for all compounds. Fingerprint plots showed the main interactions attributed to H·H C·H, O·H, Br·H, and F·H, with contacts contributing between 1.9% and 38.2%. The mass spectrometry data indicated the presence of molecular ions [M + H] + and characteristic fragmentations of the compounds, which indicated the same behavior of the compounds in solution and solid state. Molecular docking simulations were studied to evaluate the properties and interactions of the free dithiocarbazates and their Ni(II) complexes with selected proteins and DNA. These results were supported by in vitro cytotoxicity assays against four cancer cell lines, showing that the synthesized metal complexes display promising biological activity.Faculdade de Ciências da Saúde (FS)Departamento de Farmácia (FS FAR)Instituto de Química (IQ)Faculdade UnB Ceilândia (FCE)FrontiersUniversity of Brasília, Institute of Chemistry, Laboratory of Inorganic Synthesis and CrystallographyUniversity of Brasília, Faculdade UnB Ceilândia, Multidisciplinary Laboratory of Human HealthUniversity of Brasília, Faculdade UnB Ceilândia, Multidisciplinary Laboratory of Human HealthUniversity of Brasília, Institute of Chemistry, Laboratory of Computational ChemistryUniversity of Brasília, Institute of Chemistry, Laboratory of Computational ChemistryUniversity of Brasília, Faculty of Health Sciences and Medicine, Laboratory of Molecular Cancer Pathology,University of Brasília, Institute of Chemistry, Laboratory of Inorganic Synthesis and CrystallographyCavalcante, Cássia de Queiroz OliveiraMota, Tales Henrique Andrade daOliveira, Diêgo Madureira deNascimento, Érica Cristina MorenoMartins, João Batista LopesPittella-Silva, FabioGatto, Claudia Cristina2023-10-09T11:19:08Z2023-10-09T11:19:08Z2023-03-07info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfCAVALCANTE, Cássia de Q. O. et al. Dithiocarbazate ligands and their Ni(II) complexes with potential biological activity: structural, antitumor and molecular docking study. Frontiers in Molecular Biosciences, v. 10, 2023. DOI: https://doi.org/10.3389. /fmolb.2023.1146820. Disponível em: https://www.frontiersin.org/articles/10.3389/fmolb.2023.1146820/full. Acesso em: 09 out. 2023.http://repositorio2.unb.br/jspui/handle/10482/46638https://doi.org/10.3389/fmolb.2023.1146820eng© 2023 Cavalcante, da Mota, de Oliveira, Nascimento, Martins, Pittella-Silva and Gatto. This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner(s) are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms.info:eu-repo/semantics/openAccessreponame:Repositório Institucional da UnBinstname:Universidade de Brasília (UnB)instacron:UNB2024-07-15T15:05:41Zoai:repositorio.unb.br:10482/46638Repositório InstitucionalPUBhttps://repositorio.unb.br/oai/requestrepositorio@unb.bropendoar:2024-07-15T15:05:41Repositório Institucional da UnB - Universidade de Brasília (UnB)false |
dc.title.none.fl_str_mv |
Dithiocarbazate ligands and their Ni(II) complexes with potential biological activity : structural, antitumor and molecular docking study |
title |
Dithiocarbazate ligands and their Ni(II) complexes with potential biological activity : structural, antitumor and molecular docking study |
spellingShingle |
Dithiocarbazate ligands and their Ni(II) complexes with potential biological activity : structural, antitumor and molecular docking study Cavalcante, Cássia de Queiroz Oliveira Complexos de níquel (II) Ditiocarbazatos Espectrometria de massa Superfície de Hirshfeld Atividade antitumoral |
title_short |
Dithiocarbazate ligands and their Ni(II) complexes with potential biological activity : structural, antitumor and molecular docking study |
title_full |
Dithiocarbazate ligands and their Ni(II) complexes with potential biological activity : structural, antitumor and molecular docking study |
title_fullStr |
Dithiocarbazate ligands and their Ni(II) complexes with potential biological activity : structural, antitumor and molecular docking study |
title_full_unstemmed |
Dithiocarbazate ligands and their Ni(II) complexes with potential biological activity : structural, antitumor and molecular docking study |
title_sort |
Dithiocarbazate ligands and their Ni(II) complexes with potential biological activity : structural, antitumor and molecular docking study |
author |
Cavalcante, Cássia de Queiroz Oliveira |
author_facet |
Cavalcante, Cássia de Queiroz Oliveira Mota, Tales Henrique Andrade da Oliveira, Diêgo Madureira de Nascimento, Érica Cristina Moreno Martins, João Batista Lopes Pittella-Silva, Fabio Gatto, Claudia Cristina |
author_role |
author |
author2 |
Mota, Tales Henrique Andrade da Oliveira, Diêgo Madureira de Nascimento, Érica Cristina Moreno Martins, João Batista Lopes Pittella-Silva, Fabio Gatto, Claudia Cristina |
author2_role |
author author author author author author |
dc.contributor.none.fl_str_mv |
University of Brasília, Institute of Chemistry, Laboratory of Inorganic Synthesis and Crystallography University of Brasília, Faculdade UnB Ceilândia, Multidisciplinary Laboratory of Human Health University of Brasília, Faculdade UnB Ceilândia, Multidisciplinary Laboratory of Human Health University of Brasília, Institute of Chemistry, Laboratory of Computational Chemistry University of Brasília, Institute of Chemistry, Laboratory of Computational Chemistry University of Brasília, Faculty of Health Sciences and Medicine, Laboratory of Molecular Cancer Pathology, University of Brasília, Institute of Chemistry, Laboratory of Inorganic Synthesis and Crystallography |
dc.contributor.author.fl_str_mv |
Cavalcante, Cássia de Queiroz Oliveira Mota, Tales Henrique Andrade da Oliveira, Diêgo Madureira de Nascimento, Érica Cristina Moreno Martins, João Batista Lopes Pittella-Silva, Fabio Gatto, Claudia Cristina |
dc.subject.por.fl_str_mv |
Complexos de níquel (II) Ditiocarbazatos Espectrometria de massa Superfície de Hirshfeld Atividade antitumoral |
topic |
Complexos de níquel (II) Ditiocarbazatos Espectrometria de massa Superfície de Hirshfeld Atividade antitumoral |
description |
n the search for new metal complexes with antitumor potential, two dithiocarbazate ligands derived from 1,1,1-trifluoro-2,4-pentanedione (H 2 L 1) and (H2 L2 ) and four Ni(II) complexes, [Ni(L 1 )PPh3 ] (1), [Ni(L 1)Py] (2), [Ni(L2)PPh 3](3), and [Ni(L 2 )Py] (4), were successfully synthesized and investigated by physical-chemistry and spectroscopic methods. The crystal structure of the H2 L 1 and the Ni(II) complexes has been elucidated by single-crystal X-ray diffraction. The obtained structure from H 2 L 1 confirms the cyclization reaction and formation of the pyrazoline derivative. The results showed square planar geometry to the metal centers, in which dithiocarbazates coordinated by the ONS donor system and a triphenylphosphine or pyridine molecule complete the coordination sphere. Hirshfeld surface analysis by dnorm function was investigated and showed π–π stacking interactions upon the molecular packing of H 2 L1 and non-classical hydrogen bonds for all compounds. Fingerprint plots showed the main interactions attributed to H·H C·H, O·H, Br·H, and F·H, with contacts contributing between 1.9% and 38.2%. The mass spectrometry data indicated the presence of molecular ions [M + H] + and characteristic fragmentations of the compounds, which indicated the same behavior of the compounds in solution and solid state. Molecular docking simulations were studied to evaluate the properties and interactions of the free dithiocarbazates and their Ni(II) complexes with selected proteins and DNA. These results were supported by in vitro cytotoxicity assays against four cancer cell lines, showing that the synthesized metal complexes display promising biological activity. |
publishDate |
2023 |
dc.date.none.fl_str_mv |
2023-10-09T11:19:08Z 2023-10-09T11:19:08Z 2023-03-07 |
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 |
CAVALCANTE, Cássia de Q. O. et al. Dithiocarbazate ligands and their Ni(II) complexes with potential biological activity: structural, antitumor and molecular docking study. Frontiers in Molecular Biosciences, v. 10, 2023. DOI: https://doi.org/10.3389. /fmolb.2023.1146820. Disponível em: https://www.frontiersin.org/articles/10.3389/fmolb.2023.1146820/full. Acesso em: 09 out. 2023. http://repositorio2.unb.br/jspui/handle/10482/46638 https://doi.org/10.3389/fmolb.2023.1146820 |
identifier_str_mv |
CAVALCANTE, Cássia de Q. O. et al. Dithiocarbazate ligands and their Ni(II) complexes with potential biological activity: structural, antitumor and molecular docking study. Frontiers in Molecular Biosciences, v. 10, 2023. DOI: https://doi.org/10.3389. /fmolb.2023.1146820. Disponível em: https://www.frontiersin.org/articles/10.3389/fmolb.2023.1146820/full. Acesso em: 09 out. 2023. |
url |
http://repositorio2.unb.br/jspui/handle/10482/46638 https://doi.org/10.3389/fmolb.2023.1146820 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
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info:eu-repo/semantics/openAccess |
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openAccess |
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application/pdf |
dc.publisher.none.fl_str_mv |
Frontiers |
publisher.none.fl_str_mv |
Frontiers |
dc.source.none.fl_str_mv |
reponame:Repositório Institucional da UnB instname:Universidade de Brasília (UnB) instacron:UNB |
instname_str |
Universidade de Brasília (UnB) |
instacron_str |
UNB |
institution |
UNB |
reponame_str |
Repositório Institucional da UnB |
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Repositório Institucional da UnB |
repository.name.fl_str_mv |
Repositório Institucional da UnB - Universidade de Brasília (UnB) |
repository.mail.fl_str_mv |
repositorio@unb.br |
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1814508204110905344 |