Design of novel iron compounds as potential therapeutic agents against tuberculosis

Autores
Tarallo, M. Belén; Urquiola, Carolina; Monge, Antonio; Parajón Costa, Beatriz Susana; Ribeiro, Ronny R.; Costa Filho, Antonio J.; Mercader, Roberto Carlos; Pavan, Fernando R.; Leite, Clarice Q.F.; Torre, María H.; Gambino, Dinorah
Año de publicación
2010
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
In the search for new therapeutic tools against Tuberculosis two novel iron complexes, [Fe(L-H)3], with 3-aminoquinoxaline-2-carbonitrile N1,N4-dioxide derivatives (L) as ligands, were synthesized, characterized by a combination of techniques, and in vitro evaluated. Results were compared with those previously reported for two analogous iron complexes of other ligands of the same family of quinoxaline derivatives. In addition, the complexes were studied by cyclic voltammetry and electronic paramagnetic resonance (EPR) spectroscopy. Cyclic voltammograms of the iron compounds showed several cathodic processes which were attributed to the reduction of the metal center (Fe3+/Fe2+) and the coordinated ligand. EPR signals were characteristic of magnetically isolated high-spin Fe(III) in a rhombic environment and arise from transitions between mS=  1/2 (geff~9) or mS=  3/2 (geff~4.3) states. Mössbauer experiments showed hyperfine parameters that are typical of high spin Fe(III) ions in a not too distorted environment. The novel complexes showed in vitro growth inhibitory activity on Mycobacterium tuberculosis H37Rv (ATCC 27294), together with very low unspecific cytotoxicity on eucariotic cells (cultured murine cell line J774). Both complexes showed higher inhibitory effects on M. tuberculosis than the “second-line” therapeutic drugs.
Fil: Tarallo, M. Belén. Universidad de la República; Uruguay
Fil: Urquiola, Carolina. Universidad de la República; Uruguay
Fil: Monge, Antonio. Universidad de Navarra; España
Fil: Parajón Costa, Beatriz Susana. 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: Ribeiro, Ronny R.. Universidade de São Paulo. Instituto de Física de São Carlos; Brasil
Fil: Costa Filho, Antonio J.. Universidade de São Paulo. Instituto de Física de São Carlos; Brasil
Fil: Mercader, Roberto Carlos. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Física La Plata. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Física La Plata; Argentina
Fil: Pavan, Fernando R.. Universidade Estadual Paulista Julio de Mesquita Filho; Brasil
Fil: Leite, Clarice Q.F.. Universidade Estadual Paulista Julio de Mesquita Filho; Brasil
Fil: Torre, María H.. Universidad de la República; Uruguay
Fil: Gambino, Dinorah. Universidad de la República; Uruguay
Materia
Tuberculosis
Iron
Quinoxaline N1,N4 dioxides
Mycobacterium tuberculosis
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/103570
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/103570
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Design of novel iron compounds as potential therapeutic agents against tuberculosisTarallo, M. BelénUrquiola, CarolinaMonge, AntonioParajón Costa, Beatriz SusanaRibeiro, Ronny R.Costa Filho, Antonio J.Mercader, Roberto CarlosPavan, Fernando R.Leite, Clarice Q.F.Torre, María H.Gambino, DinorahTuberculosisIronQuinoxaline N1,N4 dioxidesMycobacterium tuberculosishttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1In the search for new therapeutic tools against Tuberculosis two novel iron complexes, [Fe(L-H)3], with 3-aminoquinoxaline-2-carbonitrile N1,N4-dioxide derivatives (L) as ligands, were synthesized, characterized by a combination of techniques, and in vitro evaluated. Results were compared with those previously reported for two analogous iron complexes of other ligands of the same family of quinoxaline derivatives. In addition, the complexes were studied by cyclic voltammetry and electronic paramagnetic resonance (EPR) spectroscopy. Cyclic voltammograms of the iron compounds showed several cathodic processes which were attributed to the reduction of the metal center (Fe3+/Fe2+) and the coordinated ligand. EPR signals were characteristic of magnetically isolated high-spin Fe(III) in a rhombic environment and arise from transitions between mS=  1/2 (geff~9) or mS=  3/2 (geff~4.3) states. Mössbauer experiments showed hyperfine parameters that are typical of high spin Fe(III) ions in a not too distorted environment. The novel complexes showed in vitro growth inhibitory activity on Mycobacterium tuberculosis H37Rv (ATCC 27294), together with very low unspecific cytotoxicity on eucariotic cells (cultured murine cell line J774). Both complexes showed higher inhibitory effects on M. tuberculosis than the “second-line” therapeutic drugs.Fil: Tarallo, M. Belén. Universidad de la República; UruguayFil: Urquiola, Carolina. Universidad de la República; UruguayFil: Monge, Antonio. Universidad de Navarra; EspañaFil: Parajón Costa, Beatriz Susana. 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: Ribeiro, Ronny R.. Universidade de São Paulo. Instituto de Física de São Carlos; BrasilFil: Costa Filho, Antonio J.. Universidade de São Paulo. Instituto de Física de São Carlos; BrasilFil: Mercader, Roberto Carlos. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Física La Plata. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Física La Plata; ArgentinaFil: Pavan, Fernando R.. Universidade Estadual Paulista Julio de Mesquita Filho; BrasilFil: Leite, Clarice Q.F.. Universidade Estadual Paulista Julio de Mesquita Filho; BrasilFil: Torre, María H.. Universidad de la República; UruguayFil: Gambino, Dinorah. Universidad de la República; UruguayElsevier Science Inc2010-11info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/103570Tarallo, M. Belén; Urquiola, Carolina; Monge, Antonio; Parajón Costa, Beatriz Susana; Ribeiro, Ronny R.; et al.; Design of novel iron compounds as potential therapeutic agents against tuberculosis; Elsevier Science Inc; Journal of Inorganic Biochemistry; 104; 11; 11-2010; 1164-11700162-0134CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0162013410001674info:eu-repo/semantics/altIdentifier/doi/10.1016/j.jinorgbio.2010.07.005info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-22T12:09:23Zoai:ri.conicet.gov.ar:11336/103570instacron: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:34982025-10-22 12:09:23.501CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Design of novel iron compounds as potential therapeutic agents against tuberculosis
title Design of novel iron compounds as potential therapeutic agents against tuberculosis
spellingShingle Design of novel iron compounds as potential therapeutic agents against tuberculosis
Tarallo, M. Belén
Tuberculosis
Iron
Quinoxaline N1,N4 dioxides
Mycobacterium tuberculosis
title_short Design of novel iron compounds as potential therapeutic agents against tuberculosis
title_full Design of novel iron compounds as potential therapeutic agents against tuberculosis
title_fullStr Design of novel iron compounds as potential therapeutic agents against tuberculosis
title_full_unstemmed Design of novel iron compounds as potential therapeutic agents against tuberculosis
title_sort Design of novel iron compounds as potential therapeutic agents against tuberculosis
dc.creator.none.fl_str_mv Tarallo, M. Belén
Urquiola, Carolina
Monge, Antonio
Parajón Costa, Beatriz Susana
Ribeiro, Ronny R.
Costa Filho, Antonio J.
Mercader, Roberto Carlos
Pavan, Fernando R.
Leite, Clarice Q.F.
Torre, María H.
Gambino, Dinorah
author Tarallo, M. Belén
author_facet Tarallo, M. Belén
Urquiola, Carolina
Monge, Antonio
Parajón Costa, Beatriz Susana
Ribeiro, Ronny R.
Costa Filho, Antonio J.
Mercader, Roberto Carlos
Pavan, Fernando R.
Leite, Clarice Q.F.
Torre, María H.
Gambino, Dinorah
author_role author
author2 Urquiola, Carolina
Monge, Antonio
Parajón Costa, Beatriz Susana
Ribeiro, Ronny R.
Costa Filho, Antonio J.
Mercader, Roberto Carlos
Pavan, Fernando R.
Leite, Clarice Q.F.
Torre, María H.
Gambino, Dinorah
author2_role author
author
author
author
author
author
author
author
author
author
dc.subject.none.fl_str_mv Tuberculosis
Iron
Quinoxaline N1,N4 dioxides
Mycobacterium tuberculosis
topic Tuberculosis
Iron
Quinoxaline N1,N4 dioxides
Mycobacterium tuberculosis
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv In the search for new therapeutic tools against Tuberculosis two novel iron complexes, [Fe(L-H)3], with 3-aminoquinoxaline-2-carbonitrile N1,N4-dioxide derivatives (L) as ligands, were synthesized, characterized by a combination of techniques, and in vitro evaluated. Results were compared with those previously reported for two analogous iron complexes of other ligands of the same family of quinoxaline derivatives. In addition, the complexes were studied by cyclic voltammetry and electronic paramagnetic resonance (EPR) spectroscopy. Cyclic voltammograms of the iron compounds showed several cathodic processes which were attributed to the reduction of the metal center (Fe3+/Fe2+) and the coordinated ligand. EPR signals were characteristic of magnetically isolated high-spin Fe(III) in a rhombic environment and arise from transitions between mS=  1/2 (geff~9) or mS=  3/2 (geff~4.3) states. Mössbauer experiments showed hyperfine parameters that are typical of high spin Fe(III) ions in a not too distorted environment. The novel complexes showed in vitro growth inhibitory activity on Mycobacterium tuberculosis H37Rv (ATCC 27294), together with very low unspecific cytotoxicity on eucariotic cells (cultured murine cell line J774). Both complexes showed higher inhibitory effects on M. tuberculosis than the “second-line” therapeutic drugs.
Fil: Tarallo, M. Belén. Universidad de la República; Uruguay
Fil: Urquiola, Carolina. Universidad de la República; Uruguay
Fil: Monge, Antonio. Universidad de Navarra; España
Fil: Parajón Costa, Beatriz Susana. 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: Ribeiro, Ronny R.. Universidade de São Paulo. Instituto de Física de São Carlos; Brasil
Fil: Costa Filho, Antonio J.. Universidade de São Paulo. Instituto de Física de São Carlos; Brasil
Fil: Mercader, Roberto Carlos. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Física La Plata. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Física La Plata; Argentina
Fil: Pavan, Fernando R.. Universidade Estadual Paulista Julio de Mesquita Filho; Brasil
Fil: Leite, Clarice Q.F.. Universidade Estadual Paulista Julio de Mesquita Filho; Brasil
Fil: Torre, María H.. Universidad de la República; Uruguay
Fil: Gambino, Dinorah. Universidad de la República; Uruguay
description In the search for new therapeutic tools against Tuberculosis two novel iron complexes, [Fe(L-H)3], with 3-aminoquinoxaline-2-carbonitrile N1,N4-dioxide derivatives (L) as ligands, were synthesized, characterized by a combination of techniques, and in vitro evaluated. Results were compared with those previously reported for two analogous iron complexes of other ligands of the same family of quinoxaline derivatives. In addition, the complexes were studied by cyclic voltammetry and electronic paramagnetic resonance (EPR) spectroscopy. Cyclic voltammograms of the iron compounds showed several cathodic processes which were attributed to the reduction of the metal center (Fe3+/Fe2+) and the coordinated ligand. EPR signals were characteristic of magnetically isolated high-spin Fe(III) in a rhombic environment and arise from transitions between mS=  1/2 (geff~9) or mS=  3/2 (geff~4.3) states. Mössbauer experiments showed hyperfine parameters that are typical of high spin Fe(III) ions in a not too distorted environment. The novel complexes showed in vitro growth inhibitory activity on Mycobacterium tuberculosis H37Rv (ATCC 27294), together with very low unspecific cytotoxicity on eucariotic cells (cultured murine cell line J774). Both complexes showed higher inhibitory effects on M. tuberculosis than the “second-line” therapeutic drugs.
publishDate 2010
dc.date.none.fl_str_mv 2010-11
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/11336/103570
Tarallo, M. Belén; Urquiola, Carolina; Monge, Antonio; Parajón Costa, Beatriz Susana; Ribeiro, Ronny R.; et al.; Design of novel iron compounds as potential therapeutic agents against tuberculosis; Elsevier Science Inc; Journal of Inorganic Biochemistry; 104; 11; 11-2010; 1164-1170
0162-0134
CONICET Digital
CONICET
url http://hdl.handle.net/11336/103570
identifier_str_mv Tarallo, M. Belén; Urquiola, Carolina; Monge, Antonio; Parajón Costa, Beatriz Susana; Ribeiro, Ronny R.; et al.; Design of novel iron compounds as potential therapeutic agents against tuberculosis; Elsevier Science Inc; Journal of Inorganic Biochemistry; 104; 11; 11-2010; 1164-1170
0162-0134
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0162013410001674
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.jinorgbio.2010.07.005
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Elsevier Science Inc
publisher.none.fl_str_mv Elsevier Science Inc
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 12.982451

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