Dithiocarbazate ligands and their Ni(II) complexes with potential biological activity: Structural, antitumor and molecular docking study
In the search for new metal complexes with antitumor potential, two dithiocarbazate ligands derived from 1,1,1-trifluoro-2,4-pentanedione (H2L1) and (H2L2) and four Ni(II) complexes, [Ni(L1)PPh3] (1), [Ni(L1)Py] (2), [Ni(L2)PPh3] (3), and [Ni(L2)Py] (4), were successfully synthesized and investigate...
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| Format: | Article |
| Language: | English |
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Frontiers Media S.A.
2023-03-01
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| Series: | Frontiers in Molecular Biosciences |
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| Online Access: | https://www.frontiersin.org/articles/10.3389/fmolb.2023.1146820/full |
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| author | Cássia de Q. O. Cavalcante Tales H. A. da Mota Diêgo M. de Oliveira Érica C. M. Nascimento João B. L. Martins Fabio Pittella-Silva Claudia C. Gatto |
| author_facet | Cássia de Q. O. Cavalcante Tales H. A. da Mota Diêgo M. de Oliveira Érica C. M. Nascimento João B. L. Martins Fabio Pittella-Silva Claudia C. Gatto |
| author_sort | Cássia de Q. O. Cavalcante |
| collection | DOAJ |
| description | In the search for new metal complexes with antitumor potential, two dithiocarbazate ligands derived from 1,1,1-trifluoro-2,4-pentanedione (H2L1) and (H2L2) and four Ni(II) complexes, [Ni(L1)PPh3] (1), [Ni(L1)Py] (2), [Ni(L2)PPh3] (3), and [Ni(L2)Py] (4), were successfully synthesized and investigated by physical-chemistry and spectroscopic methods. The crystal structure of the H2L1 and the Ni(II) complexes has been elucidated by single-crystal X-ray diffraction. The obtained structure from H2L1 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 H2L1 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. |
| first_indexed | 2024-04-10T05:08:36Z |
| format | Article |
| id | doaj.art-beacccfcadd54069b775edbb33e99a4b |
| institution | Directory Open Access Journal |
| issn | 2296-889X |
| language | English |
| last_indexed | 2024-04-10T05:08:36Z |
| publishDate | 2023-03-01 |
| publisher | Frontiers Media S.A. |
| record_format | Article |
| series | Frontiers in Molecular Biosciences |
| spelling | doaj.art-beacccfcadd54069b775edbb33e99a4b2023-03-09T11:29:13ZengFrontiers Media S.A.Frontiers in Molecular Biosciences2296-889X2023-03-011010.3389/fmolb.2023.11468201146820Dithiocarbazate ligands and their Ni(II) complexes with potential biological activity: Structural, antitumor and molecular docking studyCássia de Q. O. Cavalcante0Tales H. A. da Mota1Diêgo M. de Oliveira2Érica C. M. Nascimento3João B. L. Martins4Fabio Pittella-Silva5Claudia C. Gatto6University of Brasília, Institute of Chemistry, Laboratory of Inorganic Synthesis and Crystallography, Brasília, DF, BrazilUniversity of Brasília, Faculdade UnB Ceilândia, Multidisciplinary Laboratory of Human Health, Brasília, DF, BrazilUniversity of Brasília, Faculdade UnB Ceilândia, Multidisciplinary Laboratory of Human Health, Brasília, DF, BrazilUniversity of Brasília, Institute of Chemistry, Laboratory of Computational Chemistry, Brasília, DF, BrazilUniversity of Brasília, Institute of Chemistry, Laboratory of Computational Chemistry, Brasília, DF, BrazilUniversity of Brasília, Faculty of Health Sciences and Medicine, Laboratory of Molecular Cancer Pathology, Brasília, DF, BrazilUniversity of Brasília, Institute of Chemistry, Laboratory of Inorganic Synthesis and Crystallography, Brasília, DF, BrazilIn the search for new metal complexes with antitumor potential, two dithiocarbazate ligands derived from 1,1,1-trifluoro-2,4-pentanedione (H2L1) and (H2L2) and four Ni(II) complexes, [Ni(L1)PPh3] (1), [Ni(L1)Py] (2), [Ni(L2)PPh3] (3), and [Ni(L2)Py] (4), were successfully synthesized and investigated by physical-chemistry and spectroscopic methods. The crystal structure of the H2L1 and the Ni(II) complexes has been elucidated by single-crystal X-ray diffraction. The obtained structure from H2L1 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 H2L1 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.https://www.frontiersin.org/articles/10.3389/fmolb.2023.1146820/fullNi(II) complexesdithiocarbazatecrystal structuremass spectrometryHirshfeld surfaceantitumor activity |
| spellingShingle | Cássia de Q. O. Cavalcante Tales H. A. da Mota Diêgo M. de Oliveira Érica C. M. Nascimento João B. L. Martins Fabio Pittella-Silva Claudia C. Gatto Dithiocarbazate ligands and their Ni(II) complexes with potential biological activity: Structural, antitumor and molecular docking study Frontiers in Molecular Biosciences Ni(II) complexes dithiocarbazate crystal structure mass spectrometry Hirshfeld surface antitumor activity |
| title | 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_short | 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 |
| topic | Ni(II) complexes dithiocarbazate crystal structure mass spectrometry Hirshfeld surface antitumor activity |
| url | https://www.frontiersin.org/articles/10.3389/fmolb.2023.1146820/full |
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