Solution chemical properties and anticancer potential of 8-hydroxyquinoline hydrazones and their oxidovanadium(IV) complexes
We report the synthesis and characterization of a family of benzohydrazones (Ln, n = 1-6) derived from 2-carbaldehyde-8-hydroxyquinoline and benzylhydrazides containing different substituents in the para position. Their oxidovanadium(IV) complexes were prepared and compounds with 1:1 and 1:2 metal-t...
| Autores: | , , , , , , , , , , , |
|---|---|
| Tipo de recurso: | artículo |
| Fecha de publicación: | 2022 |
| País: | España |
| Institución: | Universitat Autònoma de Barcelona |
| Repositorio: | Dipòsit Digital de Documents de la UAB |
| Idioma: | inglés |
| OAI Identifier: | oai:ddd.uab.cat:288928 |
| Acceso en línea: | https://ddd.uab.cat/record/288928 https://dx.doi.org/urn:doi:10.1016/j.jinorgbio.2022.111932 |
| Access Level: | acceso abierto |
| Palabra clave: | 8-hydroxyquinoline derivatives Anticancer Oxidovanadium(IV) complexes Schiff bases Solution stability Speciation SDG 3 - Good Health and Well-being |
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Solution chemical properties and anticancer potential of 8-hydroxyquinoline hydrazones and their oxidovanadium(IV) complexesRibeiro, Nádia|||0000-0003-2725-7781Bulut, IpekPósa, VivienSergi, BarisSciortino, Giuseppe|||0000-0001-9657-1788Costa Pessoa, João|||0000-0002-3978-9964Maia, Luisa B.|||0000-0002-6901-6591Ugone, Valeria|||0000-0002-2830-3869Garribba, Eugenio|||0000-0002-7229-5966Enyedy, Éva A.|||0000-0002-8058-8128Acilan, CeydaCorreia, Isabel|||0000-0001-7096-42848-hydroxyquinoline derivativesAnticancerOxidovanadium(IV) complexesSchiff basesSolution stabilitySpeciationSDG 3 - Good Health and Well-beingWe report the synthesis and characterization of a family of benzohydrazones (Ln, n = 1-6) derived from 2-carbaldehyde-8-hydroxyquinoline and benzylhydrazides containing different substituents in the para position. Their oxidovanadium(IV) complexes were prepared and compounds with 1:1 and 1:2 metal-to-ligand stoichiometry were obtained. All compounds were characterized by elemental analyses and mass spectrometry as well as FTIR, UV-visible absorption, NMR (ligand precursors) and EPR (complexes) spectroscopies, and by DFT computational methods. Proton dissociation constants, lipophilicity and solubility in aqueous media were determined for all ligand precursors. Complex formation with V(IV)O was evaluated by spectrophotometry for L4 (Me-substituted) and L6 (OH-substituted) and formation constants for mono [VO(HL)]+, [VO(L)] and bis [VO(HL)2], [VO(HL)(L)]-, [VO(L)2]2- complexes were determined. EPR spectroscopy indicates the formation of [VO(HL)]+ and [VO(HL)2], with this latter being the major species at the physiological pH. Noteworthy, the EPR data suggest a different behaviour for L4 and L6, which confirm the results obtained in the solid state. The antiproliferative activity of all compounds was evaluated in malignant melanoma (A-375) and lung (A-549) cancer cells. All complexes show much higher activity on A-375 (IC50 < 6.3 μM) than in A-549 cells (IC50 > 20 μM). Complex 3 (F-substituted) shows the lowest IC50 on both cell lines and lower than cisplatin (in A-375). Studies identified this compound as the one showing the highest increase in Annexin-V staining, caspase activity and induction of double stranded breaks, corroborating the cytotoxicity results. The mechanism of action of the complexes involves reactive oxygen species (ROS) induced DNA damage, and cell death by apoptosis. 22022-01-0120222022-01-01Articlehttp://purl.org/coar/resource_type/c_6501VoRhttp://purl.org/coar/version/c_970fb48d4fbd8a85info:eu-repo/semantics/articleapplication/pdfhttps://ddd.uab.cat/record/288928https://dx.doi.org/urn:doi:10.1016/j.jinorgbio.2022.111932reponame:Dipòsit Digital de Documents de la UABinstname:Universitat Autònoma de BarcelonaInglésengMinisterio de Ciencia e Innovación https://doi.org/10.13039/501100004837 FJC2019-039135-Iopen accesshttp://purl.org/coar/access_right/c_abf2Aquest document està subjecte a una llicència d'ús Creative Commons. Es permet la reproducció total o parcial, la distribució, i la comunicació pública de l'obra, sempre que no sigui amb finalitats comercials, i sempre que es reconegui l'autoria de l'obra original. No es permet la creació d'obres derivades.https://creativecommons.org/licenses/by-nc-nd/4.0/info:eu-repo/semantics/openAccessoai:ddd.uab.cat:2889282026-06-06T12:50:31Z |
| dc.title.none.fl_str_mv |
Solution chemical properties and anticancer potential of 8-hydroxyquinoline hydrazones and their oxidovanadium(IV) complexes |
| title |
Solution chemical properties and anticancer potential of 8-hydroxyquinoline hydrazones and their oxidovanadium(IV) complexes |
| spellingShingle |
Solution chemical properties and anticancer potential of 8-hydroxyquinoline hydrazones and their oxidovanadium(IV) complexes Ribeiro, Nádia|||0000-0003-2725-7781 8-hydroxyquinoline derivatives Anticancer Oxidovanadium(IV) complexes Schiff bases Solution stability Speciation SDG 3 - Good Health and Well-being |
| title_short |
Solution chemical properties and anticancer potential of 8-hydroxyquinoline hydrazones and their oxidovanadium(IV) complexes |
| title_full |
Solution chemical properties and anticancer potential of 8-hydroxyquinoline hydrazones and their oxidovanadium(IV) complexes |
| title_fullStr |
Solution chemical properties and anticancer potential of 8-hydroxyquinoline hydrazones and their oxidovanadium(IV) complexes |
| title_full_unstemmed |
Solution chemical properties and anticancer potential of 8-hydroxyquinoline hydrazones and their oxidovanadium(IV) complexes |
| title_sort |
Solution chemical properties and anticancer potential of 8-hydroxyquinoline hydrazones and their oxidovanadium(IV) complexes |
| dc.creator.none.fl_str_mv |
Ribeiro, Nádia|||0000-0003-2725-7781 Bulut, Ipek Pósa, Vivien Sergi, Baris Sciortino, Giuseppe|||0000-0001-9657-1788 Costa Pessoa, João|||0000-0002-3978-9964 Maia, Luisa B.|||0000-0002-6901-6591 Ugone, Valeria|||0000-0002-2830-3869 Garribba, Eugenio|||0000-0002-7229-5966 Enyedy, Éva A.|||0000-0002-8058-8128 Acilan, Ceyda Correia, Isabel|||0000-0001-7096-4284 |
| author |
Ribeiro, Nádia|||0000-0003-2725-7781 |
| author_facet |
Ribeiro, Nádia|||0000-0003-2725-7781 Bulut, Ipek Pósa, Vivien Sergi, Baris Sciortino, Giuseppe|||0000-0001-9657-1788 Costa Pessoa, João|||0000-0002-3978-9964 Maia, Luisa B.|||0000-0002-6901-6591 Ugone, Valeria|||0000-0002-2830-3869 Garribba, Eugenio|||0000-0002-7229-5966 Enyedy, Éva A.|||0000-0002-8058-8128 Acilan, Ceyda Correia, Isabel|||0000-0001-7096-4284 |
| author_role |
author |
| author2 |
Bulut, Ipek Pósa, Vivien Sergi, Baris Sciortino, Giuseppe|||0000-0001-9657-1788 Costa Pessoa, João|||0000-0002-3978-9964 Maia, Luisa B.|||0000-0002-6901-6591 Ugone, Valeria|||0000-0002-2830-3869 Garribba, Eugenio|||0000-0002-7229-5966 Enyedy, Éva A.|||0000-0002-8058-8128 Acilan, Ceyda Correia, Isabel|||0000-0001-7096-4284 |
| author2_role |
author author author author author author author author author author author |
| dc.subject.none.fl_str_mv |
8-hydroxyquinoline derivatives Anticancer Oxidovanadium(IV) complexes Schiff bases Solution stability Speciation SDG 3 - Good Health and Well-being |
| topic |
8-hydroxyquinoline derivatives Anticancer Oxidovanadium(IV) complexes Schiff bases Solution stability Speciation SDG 3 - Good Health and Well-being |
| description |
We report the synthesis and characterization of a family of benzohydrazones (Ln, n = 1-6) derived from 2-carbaldehyde-8-hydroxyquinoline and benzylhydrazides containing different substituents in the para position. Their oxidovanadium(IV) complexes were prepared and compounds with 1:1 and 1:2 metal-to-ligand stoichiometry were obtained. All compounds were characterized by elemental analyses and mass spectrometry as well as FTIR, UV-visible absorption, NMR (ligand precursors) and EPR (complexes) spectroscopies, and by DFT computational methods. Proton dissociation constants, lipophilicity and solubility in aqueous media were determined for all ligand precursors. Complex formation with V(IV)O was evaluated by spectrophotometry for L4 (Me-substituted) and L6 (OH-substituted) and formation constants for mono [VO(HL)]+, [VO(L)] and bis [VO(HL)2], [VO(HL)(L)]-, [VO(L)2]2- complexes were determined. EPR spectroscopy indicates the formation of [VO(HL)]+ and [VO(HL)2], with this latter being the major species at the physiological pH. Noteworthy, the EPR data suggest a different behaviour for L4 and L6, which confirm the results obtained in the solid state. The antiproliferative activity of all compounds was evaluated in malignant melanoma (A-375) and lung (A-549) cancer cells. All complexes show much higher activity on A-375 (IC50 < 6.3 μM) than in A-549 cells (IC50 > 20 μM). Complex 3 (F-substituted) shows the lowest IC50 on both cell lines and lower than cisplatin (in A-375). Studies identified this compound as the one showing the highest increase in Annexin-V staining, caspase activity and induction of double stranded breaks, corroborating the cytotoxicity results. The mechanism of action of the complexes involves reactive oxygen species (ROS) induced DNA damage, and cell death by apoptosis. |
| publishDate |
2022 |
| dc.date.none.fl_str_mv |
2 2022-01-01 2022 2022-01-01 |
| dc.type.none.fl_str_mv |
Article http://purl.org/coar/resource_type/c_6501 VoR http://purl.org/coar/version/c_970fb48d4fbd8a85 |
| dc.type.openaire.fl_str_mv |
info:eu-repo/semantics/article |
| format |
article |
| dc.identifier.none.fl_str_mv |
https://ddd.uab.cat/record/288928 https://dx.doi.org/urn:doi:10.1016/j.jinorgbio.2022.111932 |
| url |
https://ddd.uab.cat/record/288928 https://dx.doi.org/urn:doi:10.1016/j.jinorgbio.2022.111932 |
| dc.language.none.fl_str_mv |
Inglés eng |
| language_invalid_str_mv |
Inglés |
| language |
eng |
| dc.relation.none.fl_str_mv |
Ministerio de Ciencia e Innovación https://doi.org/10.13039/501100004837 FJC2019-039135-I |
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open access http://purl.org/coar/access_right/c_abf2 https://creativecommons.org/licenses/by-nc-nd/4.0/ |
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info:eu-repo/semantics/openAccess |
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open access http://purl.org/coar/access_right/c_abf2 https://creativecommons.org/licenses/by-nc-nd/4.0/ |
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openAccess |
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application/pdf |
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reponame:Dipòsit Digital de Documents de la UAB instname:Universitat Autònoma de Barcelona |
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