Synthesis, Crystal Structure, Spectroscopic Characterization, DFT Calculations and Cytotoxicity Assays of a New Cu(II) Complex with an Acylhydrazone Ligand Derived from Thiophene

Autores
Rodríguez, María Rosa; Balsa, Lucía Mariana; Piro, Oscar Enrique; Echeverría, Gustavo Alberto; García-Tojal, Javier; Pis Diez, Reinaldo; León, Ignacio Esteban; Parajón Costa, Beatriz Susana; González Baró, Ana Cecilia
Año de publicación
2021
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Anew Cu(II) complex is synthetized by the reaction of copper nitrate and aN-acylhydrazone ligand obtained from the condensation of o-vanillin and 2-thiophecarbohydrazide (H2L). The solidstate structure of [Cu(HL)(H2O)](NO3) H2O, or CuHL for simplicity, was determined by X-ray diffraction. In the cationic complex, the copper center is in a nearly squared planar environment with the nitrate interacting as a counterion. CuHL was characterized by spectroscopic techniques, including solid-state FTIR, Raman, electron paramagnetic resonance (EPR) and diffuse reflectance and solution UV-Vis electronic spectroscopy. Calculations based on the density functional theory (DFT) assisted the interpretation and assignment of the spectroscopic data. The complex does not show relevant antioxidant activity evaluated by the radical cation of 2,20-azinobis(3-ethylbenzothiazoline- 6-sulfonic acid) diammonium salt (ABTS) method, being even less active than the free ligand as a radical quencher. Cytotoxicity assays of CuHL against three human tumor cell lines, namely MG-63, A549 and HT-29, revealed an important enhancement of the effectiveness as compared with both the ligand and the free metal ion. Moreover, its cytotoxic effect was remarkably stronger than that of the reference metallodrug cisplatin in all cancer cell lines tested, a promissory result in the search for new metallodrugs of essential transition metals.
Centro de Química Inorgánica
Instituto de Física La Plata
Materia
Química
copper(II) complex
N-acylhydrazone
spectroscopy
XRD crystal structure
DFT calculations
anti-cancer activity
Nivel de accesibilidad
acceso abierto
Condiciones de uso
http://creativecommons.org/licenses/by/4.0/
Repositorio
SEDICI (UNLP)
Institución
Universidad Nacional de La Plata
OAI Identificador
oai:sedici.unlp.edu.ar:10915/118872

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network_name_str SEDICI (UNLP)
spelling Synthesis, Crystal Structure, Spectroscopic Characterization, DFT Calculations and Cytotoxicity Assays of a New Cu(II) Complex with an Acylhydrazone Ligand Derived from ThiopheneRodríguez, María RosaBalsa, Lucía MarianaPiro, Oscar EnriqueEcheverría, Gustavo AlbertoGarcía-Tojal, JavierPis Diez, ReinaldoLeón, Ignacio EstebanParajón Costa, Beatriz SusanaGonzález Baró, Ana CeciliaQuímicacopper(II) complexN-acylhydrazonespectroscopyXRD crystal structureDFT calculationsanti-cancer activityAnew Cu(II) complex is synthetized by the reaction of copper nitrate and aN-acylhydrazone ligand obtained from the condensation of o-vanillin and 2-thiophecarbohydrazide (H2L). The solidstate structure of [Cu(HL)(H2O)](NO3) H2O, or CuHL for simplicity, was determined by X-ray diffraction. In the cationic complex, the copper center is in a nearly squared planar environment with the nitrate interacting as a counterion. CuHL was characterized by spectroscopic techniques, including solid-state FTIR, Raman, electron paramagnetic resonance (EPR) and diffuse reflectance and solution UV-Vis electronic spectroscopy. Calculations based on the density functional theory (DFT) assisted the interpretation and assignment of the spectroscopic data. The complex does not show relevant antioxidant activity evaluated by the radical cation of 2,20-azinobis(3-ethylbenzothiazoline- 6-sulfonic acid) diammonium salt (ABTS) method, being even less active than the free ligand as a radical quencher. Cytotoxicity assays of CuHL against three human tumor cell lines, namely MG-63, A549 and HT-29, revealed an important enhancement of the effectiveness as compared with both the ligand and the free metal ion. Moreover, its cytotoxic effect was remarkably stronger than that of the reference metallodrug cisplatin in all cancer cell lines tested, a promissory result in the search for new metallodrugs of essential transition metals.Centro de Química InorgánicaInstituto de Física La Plata2021info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionArticulohttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfhttp://sedici.unlp.edu.ar/handle/10915/118872enginfo:eu-repo/semantics/altIdentifier/issn/2304-6740info:eu-repo/semantics/altIdentifier/doi/10.3390/inorganics9020009info:eu-repo/semantics/openAccesshttp://creativecommons.org/licenses/by/4.0/Creative Commons Attribution 4.0 International (CC BY 4.0)reponame:SEDICI (UNLP)instname:Universidad Nacional de La Platainstacron:UNLP2025-09-29T11:27:59Zoai:sedici.unlp.edu.ar:10915/118872Institucionalhttp://sedici.unlp.edu.ar/Universidad públicaNo correspondehttp://sedici.unlp.edu.ar/oai/snrdalira@sedici.unlp.edu.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:13292025-09-29 11:28:00.09SEDICI (UNLP) - Universidad Nacional de La Platafalse
dc.title.none.fl_str_mv Synthesis, Crystal Structure, Spectroscopic Characterization, DFT Calculations and Cytotoxicity Assays of a New Cu(II) Complex with an Acylhydrazone Ligand Derived from Thiophene
title Synthesis, Crystal Structure, Spectroscopic Characterization, DFT Calculations and Cytotoxicity Assays of a New Cu(II) Complex with an Acylhydrazone Ligand Derived from Thiophene
spellingShingle Synthesis, Crystal Structure, Spectroscopic Characterization, DFT Calculations and Cytotoxicity Assays of a New Cu(II) Complex with an Acylhydrazone Ligand Derived from Thiophene
Rodríguez, María Rosa
Química
copper(II) complex
N-acylhydrazone
spectroscopy
XRD crystal structure
DFT calculations
anti-cancer activity
title_short Synthesis, Crystal Structure, Spectroscopic Characterization, DFT Calculations and Cytotoxicity Assays of a New Cu(II) Complex with an Acylhydrazone Ligand Derived from Thiophene
title_full Synthesis, Crystal Structure, Spectroscopic Characterization, DFT Calculations and Cytotoxicity Assays of a New Cu(II) Complex with an Acylhydrazone Ligand Derived from Thiophene
title_fullStr Synthesis, Crystal Structure, Spectroscopic Characterization, DFT Calculations and Cytotoxicity Assays of a New Cu(II) Complex with an Acylhydrazone Ligand Derived from Thiophene
title_full_unstemmed Synthesis, Crystal Structure, Spectroscopic Characterization, DFT Calculations and Cytotoxicity Assays of a New Cu(II) Complex with an Acylhydrazone Ligand Derived from Thiophene
title_sort Synthesis, Crystal Structure, Spectroscopic Characterization, DFT Calculations and Cytotoxicity Assays of a New Cu(II) Complex with an Acylhydrazone Ligand Derived from Thiophene
dc.creator.none.fl_str_mv Rodríguez, María Rosa
Balsa, Lucía Mariana
Piro, Oscar Enrique
Echeverría, Gustavo Alberto
García-Tojal, Javier
Pis Diez, Reinaldo
León, Ignacio Esteban
Parajón Costa, Beatriz Susana
González Baró, Ana Cecilia
author Rodríguez, María Rosa
author_facet Rodríguez, María Rosa
Balsa, Lucía Mariana
Piro, Oscar Enrique
Echeverría, Gustavo Alberto
García-Tojal, Javier
Pis Diez, Reinaldo
León, Ignacio Esteban
Parajón Costa, Beatriz Susana
González Baró, Ana Cecilia
author_role author
author2 Balsa, Lucía Mariana
Piro, Oscar Enrique
Echeverría, Gustavo Alberto
García-Tojal, Javier
Pis Diez, Reinaldo
León, Ignacio Esteban
Parajón Costa, Beatriz Susana
González Baró, Ana Cecilia
author2_role author
author
author
author
author
author
author
author
dc.subject.none.fl_str_mv Química
copper(II) complex
N-acylhydrazone
spectroscopy
XRD crystal structure
DFT calculations
anti-cancer activity
topic Química
copper(II) complex
N-acylhydrazone
spectroscopy
XRD crystal structure
DFT calculations
anti-cancer activity
dc.description.none.fl_txt_mv Anew Cu(II) complex is synthetized by the reaction of copper nitrate and aN-acylhydrazone ligand obtained from the condensation of o-vanillin and 2-thiophecarbohydrazide (H2L). The solidstate structure of [Cu(HL)(H2O)](NO3) H2O, or CuHL for simplicity, was determined by X-ray diffraction. In the cationic complex, the copper center is in a nearly squared planar environment with the nitrate interacting as a counterion. CuHL was characterized by spectroscopic techniques, including solid-state FTIR, Raman, electron paramagnetic resonance (EPR) and diffuse reflectance and solution UV-Vis electronic spectroscopy. Calculations based on the density functional theory (DFT) assisted the interpretation and assignment of the spectroscopic data. The complex does not show relevant antioxidant activity evaluated by the radical cation of 2,20-azinobis(3-ethylbenzothiazoline- 6-sulfonic acid) diammonium salt (ABTS) method, being even less active than the free ligand as a radical quencher. Cytotoxicity assays of CuHL against three human tumor cell lines, namely MG-63, A549 and HT-29, revealed an important enhancement of the effectiveness as compared with both the ligand and the free metal ion. Moreover, its cytotoxic effect was remarkably stronger than that of the reference metallodrug cisplatin in all cancer cell lines tested, a promissory result in the search for new metallodrugs of essential transition metals.
Centro de Química Inorgánica
Instituto de Física La Plata
description Anew Cu(II) complex is synthetized by the reaction of copper nitrate and aN-acylhydrazone ligand obtained from the condensation of o-vanillin and 2-thiophecarbohydrazide (H2L). The solidstate structure of [Cu(HL)(H2O)](NO3) H2O, or CuHL for simplicity, was determined by X-ray diffraction. In the cationic complex, the copper center is in a nearly squared planar environment with the nitrate interacting as a counterion. CuHL was characterized by spectroscopic techniques, including solid-state FTIR, Raman, electron paramagnetic resonance (EPR) and diffuse reflectance and solution UV-Vis electronic spectroscopy. Calculations based on the density functional theory (DFT) assisted the interpretation and assignment of the spectroscopic data. The complex does not show relevant antioxidant activity evaluated by the radical cation of 2,20-azinobis(3-ethylbenzothiazoline- 6-sulfonic acid) diammonium salt (ABTS) method, being even less active than the free ligand as a radical quencher. Cytotoxicity assays of CuHL against three human tumor cell lines, namely MG-63, A549 and HT-29, revealed an important enhancement of the effectiveness as compared with both the ligand and the free metal ion. Moreover, its cytotoxic effect was remarkably stronger than that of the reference metallodrug cisplatin in all cancer cell lines tested, a promissory result in the search for new metallodrugs of essential transition metals.
publishDate 2021
dc.date.none.fl_str_mv 2021
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
Articulo
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info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://sedici.unlp.edu.ar/handle/10915/118872
url http://sedici.unlp.edu.ar/handle/10915/118872
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language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/issn/2304-6740
info:eu-repo/semantics/altIdentifier/doi/10.3390/inorganics9020009
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by/4.0/
Creative Commons Attribution 4.0 International (CC BY 4.0)
eu_rights_str_mv openAccess
rights_invalid_str_mv http://creativecommons.org/licenses/by/4.0/
Creative Commons Attribution 4.0 International (CC BY 4.0)
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repository.name.fl_str_mv SEDICI (UNLP) - Universidad Nacional de La Plata
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