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
.jpg)
- Institución
- Universidad Nacional de La Plata
- OAI Identificador
- oai:sedici.unlp.edu.ar:10915/118872
Ver los metadatos del registro completo
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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:UNLP2025-10-15T11:19:51Zoai: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:13292025-10-15 11:19:51.503SEDICI (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 |
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2021 |
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article |
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eng |
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eng |
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