Synthesis and characterization of novel copper(II)-sunitinib complex: Molecular docking, DFT studies, Hirshfeld analysis and cytotoxicity studies

Autores
Tarasi, Facundo; Lanza Castronuovo, Priscila Ailin; Ferreti, Valeria; Echeverría, Gustavo Alberto; Piro, Oscar Enrique; Cacicedo, Maximiliano Luis; Gehring, Stephan; Leon, Ignacio Esteban; Islas, María Soledad
Año de publicación
2021
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The main goal of this work was to report the synthesis, characterization, and cytotoxicity study of a novel copper(II)-sunitinib complex, CuSun. It has been synthesized and characterized in solid state and in solution by different methods (such as DFT, FTIR, Raman, UV-vis, EPR, NMR, etc.). The solid-state molecular structure of trichlorosunitinibcopper(II), where sunitinib: N-[2-(diethylamino)ethyl]-5-[(Z)-(5-fluoro-2-oxo-1H-indol-3-ylidene)methyl]-2,4-dimethyl-1Hpyrrole-3-carboxamide, for short Cu(Sun)Cl3, was determined by X-ray diffraction. It crystallizes in the triclinic space group P-1 with a = 7.9061(5) Å, b = 12.412(1) Å, c = 13.7005(8) Å, α = 105.021(6)◦, β = 106.744(5)◦, γ = 91.749(5)◦, and Z = 2 molecules per unit cell. Also, we have found π-π interactions and classic and non-classic H-bonds in the crystal structure by using Hirshfeld surface analysis. In the speciation studies, the complex has dissociated in protonated sunitinib and chlorocomplex of copper(II), according to1HNMR, EPR, UV-vis and conductimetric analysis. Molecular docking of the complex in both, ATP binding site and allosteric site of VEGFR2 have shown no improvement in comparison to the free ligand. Besides, cytotoxicity assay on HepG2 cell line shows similar activity for complex and ligand in the range between 1–25 µM supporting the data obtained from studies in solution.
Fil: Tarasi, Facundo. Universidad Nacional de Mar del Plata. Facultad de Ciencias Exactas y Naturales. Departamento de Química; Argentina
Fil: Lanza Castronuovo, Priscila Ailin. Consejo Nacional de Investigaciones Cientificas y Tecnicas. Centro Cientifico Tecnologico Conicet - Mar del Plata. Instituto de Investigaciones En Biodiversidad y Biotecnologia. Grupo de Investigacion En Quimica Analitica y Modelado Molecular.; Argentina
Fil: Ferreti, Valeria. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; Argentina
Fil: Echeverría, Gustavo Alberto. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Física; Argentina
Fil: Piro, Oscar Enrique. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Física; Argentina
Fil: Cacicedo, Maximiliano Luis. Johannes Gutenberg Universitat Mainz; Alemania
Fil: Gehring, Stephan. Johannes Gutenberg Universitat Mainz; Alemania
Fil: Leon, Ignacio Esteban. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; Argentina
Fil: Islas, María Soledad. Universidad Nacional de Mar del Plata. Facultad de Ciencias Exactas y Naturales. Departamento de Química; Argentina
Materia
SUNITINIB
COPPER
COORDINATION-COMPLEXES
DOCKING
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/161063
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/161063
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Synthesis and characterization of novel copper(II)-sunitinib complex: Molecular docking, DFT studies, Hirshfeld analysis and cytotoxicity studiesTarasi, FacundoLanza Castronuovo, Priscila AilinFerreti, ValeriaEcheverría, Gustavo AlbertoPiro, Oscar EnriqueCacicedo, Maximiliano LuisGehring, StephanLeon, Ignacio EstebanIslas, María SoledadSUNITINIBCOPPERCOORDINATION-COMPLEXESDOCKINGhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The main goal of this work was to report the synthesis, characterization, and cytotoxicity study of a novel copper(II)-sunitinib complex, CuSun. It has been synthesized and characterized in solid state and in solution by different methods (such as DFT, FTIR, Raman, UV-vis, EPR, NMR, etc.). The solid-state molecular structure of trichlorosunitinibcopper(II), where sunitinib: N-[2-(diethylamino)ethyl]-5-[(Z)-(5-fluoro-2-oxo-1H-indol-3-ylidene)methyl]-2,4-dimethyl-1Hpyrrole-3-carboxamide, for short Cu(Sun)Cl3, was determined by X-ray diffraction. It crystallizes in the triclinic space group P-1 with a = 7.9061(5) Å, b = 12.412(1) Å, c = 13.7005(8) Å, α = 105.021(6)◦, β = 106.744(5)◦, γ = 91.749(5)◦, and Z = 2 molecules per unit cell. Also, we have found π-π interactions and classic and non-classic H-bonds in the crystal structure by using Hirshfeld surface analysis. In the speciation studies, the complex has dissociated in protonated sunitinib and chlorocomplex of copper(II), according to1HNMR, EPR, UV-vis and conductimetric analysis. Molecular docking of the complex in both, ATP binding site and allosteric site of VEGFR2 have shown no improvement in comparison to the free ligand. Besides, cytotoxicity assay on HepG2 cell line shows similar activity for complex and ligand in the range between 1–25 µM supporting the data obtained from studies in solution.Fil: Tarasi, Facundo. Universidad Nacional de Mar del Plata. Facultad de Ciencias Exactas y Naturales. Departamento de Química; ArgentinaFil: Lanza Castronuovo, Priscila Ailin. Consejo Nacional de Investigaciones Cientificas y Tecnicas. Centro Cientifico Tecnologico Conicet - Mar del Plata. Instituto de Investigaciones En Biodiversidad y Biotecnologia. Grupo de Investigacion En Quimica Analitica y Modelado Molecular.; ArgentinaFil: Ferreti, Valeria. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; ArgentinaFil: Echeverría, Gustavo Alberto. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Física; ArgentinaFil: Piro, Oscar Enrique. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Física; ArgentinaFil: Cacicedo, Maximiliano Luis. Johannes Gutenberg Universitat Mainz; AlemaniaFil: Gehring, Stephan. Johannes Gutenberg Universitat Mainz; AlemaniaFil: Leon, Ignacio Esteban. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; ArgentinaFil: Islas, María Soledad. Universidad Nacional de Mar del Plata. Facultad de Ciencias Exactas y Naturales. Departamento de Química; ArgentinaMDPI2021-12info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/161063Tarasi, Facundo; Lanza Castronuovo, Priscila Ailin; Ferreti, Valeria; Echeverría, Gustavo Alberto; Piro, Oscar Enrique; et al.; Synthesis and characterization of novel copper(II)-sunitinib complex: Molecular docking, DFT studies, Hirshfeld analysis and cytotoxicity studies; MDPI; Inorganics; 10; 3; 12-2021; 1-162304-6740CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.3390/inorganics10010003info:eu-repo/semantics/altIdentifier/url/https://www.mdpi.com/2304-6740/10/1/3info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:50:45Zoai:ri.conicet.gov.ar:11336/161063instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-29 09:50:45.353CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthesis and characterization of novel copper(II)-sunitinib complex: Molecular docking, DFT studies, Hirshfeld analysis and cytotoxicity studies
title Synthesis and characterization of novel copper(II)-sunitinib complex: Molecular docking, DFT studies, Hirshfeld analysis and cytotoxicity studies
spellingShingle Synthesis and characterization of novel copper(II)-sunitinib complex: Molecular docking, DFT studies, Hirshfeld analysis and cytotoxicity studies
Tarasi, Facundo
SUNITINIB
COPPER
COORDINATION-COMPLEXES
DOCKING
title_short Synthesis and characterization of novel copper(II)-sunitinib complex: Molecular docking, DFT studies, Hirshfeld analysis and cytotoxicity studies
title_full Synthesis and characterization of novel copper(II)-sunitinib complex: Molecular docking, DFT studies, Hirshfeld analysis and cytotoxicity studies
title_fullStr Synthesis and characterization of novel copper(II)-sunitinib complex: Molecular docking, DFT studies, Hirshfeld analysis and cytotoxicity studies
title_full_unstemmed Synthesis and characterization of novel copper(II)-sunitinib complex: Molecular docking, DFT studies, Hirshfeld analysis and cytotoxicity studies
title_sort Synthesis and characterization of novel copper(II)-sunitinib complex: Molecular docking, DFT studies, Hirshfeld analysis and cytotoxicity studies
dc.creator.none.fl_str_mv Tarasi, Facundo
Lanza Castronuovo, Priscila Ailin
Ferreti, Valeria
Echeverría, Gustavo Alberto
Piro, Oscar Enrique
Cacicedo, Maximiliano Luis
Gehring, Stephan
Leon, Ignacio Esteban
Islas, María Soledad
author Tarasi, Facundo
author_facet Tarasi, Facundo
Lanza Castronuovo, Priscila Ailin
Ferreti, Valeria
Echeverría, Gustavo Alberto
Piro, Oscar Enrique
Cacicedo, Maximiliano Luis
Gehring, Stephan
Leon, Ignacio Esteban
Islas, María Soledad
author_role author
author2 Lanza Castronuovo, Priscila Ailin
Ferreti, Valeria
Echeverría, Gustavo Alberto
Piro, Oscar Enrique
Cacicedo, Maximiliano Luis
Gehring, Stephan
Leon, Ignacio Esteban
Islas, María Soledad
author2_role author
author
author
author
author
author
author
author
dc.subject.none.fl_str_mv SUNITINIB
COPPER
COORDINATION-COMPLEXES
DOCKING
topic SUNITINIB
COPPER
COORDINATION-COMPLEXES
DOCKING
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv The main goal of this work was to report the synthesis, characterization, and cytotoxicity study of a novel copper(II)-sunitinib complex, CuSun. It has been synthesized and characterized in solid state and in solution by different methods (such as DFT, FTIR, Raman, UV-vis, EPR, NMR, etc.). The solid-state molecular structure of trichlorosunitinibcopper(II), where sunitinib: N-[2-(diethylamino)ethyl]-5-[(Z)-(5-fluoro-2-oxo-1H-indol-3-ylidene)methyl]-2,4-dimethyl-1Hpyrrole-3-carboxamide, for short Cu(Sun)Cl3, was determined by X-ray diffraction. It crystallizes in the triclinic space group P-1 with a = 7.9061(5) Å, b = 12.412(1) Å, c = 13.7005(8) Å, α = 105.021(6)◦, β = 106.744(5)◦, γ = 91.749(5)◦, and Z = 2 molecules per unit cell. Also, we have found π-π interactions and classic and non-classic H-bonds in the crystal structure by using Hirshfeld surface analysis. In the speciation studies, the complex has dissociated in protonated sunitinib and chlorocomplex of copper(II), according to1HNMR, EPR, UV-vis and conductimetric analysis. Molecular docking of the complex in both, ATP binding site and allosteric site of VEGFR2 have shown no improvement in comparison to the free ligand. Besides, cytotoxicity assay on HepG2 cell line shows similar activity for complex and ligand in the range between 1–25 µM supporting the data obtained from studies in solution.
Fil: Tarasi, Facundo. Universidad Nacional de Mar del Plata. Facultad de Ciencias Exactas y Naturales. Departamento de Química; Argentina
Fil: Lanza Castronuovo, Priscila Ailin. Consejo Nacional de Investigaciones Cientificas y Tecnicas. Centro Cientifico Tecnologico Conicet - Mar del Plata. Instituto de Investigaciones En Biodiversidad y Biotecnologia. Grupo de Investigacion En Quimica Analitica y Modelado Molecular.; Argentina
Fil: Ferreti, Valeria. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; Argentina
Fil: Echeverría, Gustavo Alberto. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Física; Argentina
Fil: Piro, Oscar Enrique. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Física; Argentina
Fil: Cacicedo, Maximiliano Luis. Johannes Gutenberg Universitat Mainz; Alemania
Fil: Gehring, Stephan. Johannes Gutenberg Universitat Mainz; Alemania
Fil: Leon, Ignacio Esteban. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; Argentina
Fil: Islas, María Soledad. Universidad Nacional de Mar del Plata. Facultad de Ciencias Exactas y Naturales. Departamento de Química; Argentina
description The main goal of this work was to report the synthesis, characterization, and cytotoxicity study of a novel copper(II)-sunitinib complex, CuSun. It has been synthesized and characterized in solid state and in solution by different methods (such as DFT, FTIR, Raman, UV-vis, EPR, NMR, etc.). The solid-state molecular structure of trichlorosunitinibcopper(II), where sunitinib: N-[2-(diethylamino)ethyl]-5-[(Z)-(5-fluoro-2-oxo-1H-indol-3-ylidene)methyl]-2,4-dimethyl-1Hpyrrole-3-carboxamide, for short Cu(Sun)Cl3, was determined by X-ray diffraction. It crystallizes in the triclinic space group P-1 with a = 7.9061(5) Å, b = 12.412(1) Å, c = 13.7005(8) Å, α = 105.021(6)◦, β = 106.744(5)◦, γ = 91.749(5)◦, and Z = 2 molecules per unit cell. Also, we have found π-π interactions and classic and non-classic H-bonds in the crystal structure by using Hirshfeld surface analysis. In the speciation studies, the complex has dissociated in protonated sunitinib and chlorocomplex of copper(II), according to1HNMR, EPR, UV-vis and conductimetric analysis. Molecular docking of the complex in both, ATP binding site and allosteric site of VEGFR2 have shown no improvement in comparison to the free ligand. Besides, cytotoxicity assay on HepG2 cell line shows similar activity for complex and ligand in the range between 1–25 µM supporting the data obtained from studies in solution.
publishDate 2021
dc.date.none.fl_str_mv 2021-12
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/161063
Tarasi, Facundo; Lanza Castronuovo, Priscila Ailin; Ferreti, Valeria; Echeverría, Gustavo Alberto; Piro, Oscar Enrique; et al.; Synthesis and characterization of novel copper(II)-sunitinib complex: Molecular docking, DFT studies, Hirshfeld analysis and cytotoxicity studies; MDPI; Inorganics; 10; 3; 12-2021; 1-16
2304-6740
CONICET Digital
CONICET
url http://hdl.handle.net/11336/161063
identifier_str_mv Tarasi, Facundo; Lanza Castronuovo, Priscila Ailin; Ferreti, Valeria; Echeverría, Gustavo Alberto; Piro, Oscar Enrique; et al.; Synthesis and characterization of novel copper(II)-sunitinib complex: Molecular docking, DFT studies, Hirshfeld analysis and cytotoxicity studies; MDPI; Inorganics; 10; 3; 12-2021; 1-16
2304-6740
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.3390/inorganics10010003
info:eu-repo/semantics/altIdentifier/url/https://www.mdpi.com/2304-6740/10/1/3
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv MDPI
publisher.none.fl_str_mv MDPI
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 13.070432

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