Dithiocarbazate ligands and their Ni(II) complexes with potential biological activity : structural, antitumor and molecular docking study

Detalhes bibliográficos
Autor(a) principal: Cavalcante, Cássia de Queiroz Oliveira
Data de Publicação: 2023
Outros Autores: Mota, Tales Henrique Andrade da, Oliveira, Diêgo Madureira de, Nascimento, Érica Cristina Moreno, Martins, João Batista Lopes, Pittella-Silva, Fabio, Gatto, Claudia Cristina
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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spelling 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
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 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
collection 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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