Oxidovanadium(IV) and dioxidovanadium(V) complexes of tridentate salicylaldehyde semicarbazones: Searching for prospective antitrypanosomal agents
- Autores
- Fernández, Mariana; Becco, Lorena; Correia, Isabel; Benítez, Julio; Piro, Oscar Enrique; Echeverría, Gustavo Alberto; Medeiros, Andrea; Comini, Marcelo; Lavaggi, María Laura; González, Mercedes; Cerecetto, Hugo; Moreno, Virtudes; Costa Pessoa, Joao; Garat, Beatriz; Gambino, Dinorah
- Año de publicación
- 2013
- Idioma
- inglés
- Tipo de recurso
- artículo
- Estado
- versión publicada
- Descripción
- As a contribution to the identification of the relevant species for biological activity and the understanding of structure–activity relationships of [VIVO(L-2H)(NN)] antitrypanosomal complexes (NN is a bidentate polypyridyl DNA intercalator; L is a tridentate salicylaldehyde semicarbazone derivative), new [VVO2(L-2H)] complexes and [VIVO(L-2H)(NN)] complexes including bipy or dppz (dipyrido[3,2-a: 2′,3′-c]phenazine) co-ligands are prepared and characterized in the solid state and in solution. Their activity is evaluated on Trypanosoma cruzi. The lipophilicity, as structural descriptor related to bioactivity, of the whole [VIVO(L-2H)(NN)] series is determined. Furthermore, the antiproliferative effect of those new compounds showing activity against T. cruzi is evaluated on the genetically related parasite T. brucei with the aim to develop broad spectrum agents. The new [VIVO(L-2H)(dppz)] complexes are about ten to fifteen times more toxic to T. cruzi than the bipy analogues and show quite good in vitro activity on T. brucei brucei. They are shown to interact with DNA, suggesting that this biomolecule may be the parasite target. The stability of the VIVO-complexes in solution is accessed by several techniques. Globally the data suggest that the relevant species for biological activity are the [VIVO(L-2H)(NN)] compounds, their order of activity being dependent on the NN nature, but not much on the substitution on the salicylaldehyde semicarbazone moiety. A parabolic relationship between biological response and lipophilicity (determined as RM = log [(1 / Rf) − 1] by a TLC method) is obtained. From this correlation an optimum RM value, close to 1.44, was found, which may be used as design guide for future development of antitrypanosomal compounds.
Fil: Fernández, Mariana. Universidad de la República; Uruguay
Fil: Becco, Lorena. Universidad de la República; Uruguay
Fil: Correia, Isabel. Universidade Técnica de Lisboa; Portugal
Fil: Benítez, Julio. Universidad de la República; Uruguay
Fil: Piro, Oscar Enrique. 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. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Física; Argentina
Fil: Echeverría, Gustavo Alberto. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Física; Argentina. 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: Medeiros, Andrea. Universidad de la República; Uruguay. Instituto Pasteur de Montevideo; Uruguay
Fil: Comini, Marcelo. Instituto Pasteur de Montevideo; Uruguay
Fil: Lavaggi, María Laura. Universidad de la República; Uruguay
Fil: González, Mercedes. Universidad de la República; Uruguay
Fil: Cerecetto, Hugo. Universidad de la República; Uruguay
Fil: Moreno, Virtudes. Universidad de Barcelona; España
Fil: Costa Pessoa, Joao. Universidade Técnica de Lisboa; Portugal
Fil: Garat, Beatriz. Universidad de la República; Uruguay
Fil: Gambino, Dinorah. Universidad de la República; Uruguay - Materia
-
Oxidovanadium(Iv) Complexes
Dioxidovanadium(V) Complexes
Salicylaldehyde Semicarbazones
Antitrypanosomal
2,2¡Ä-Bipyridine, Dipyrido[3,2-A: 2¡Ä,3¡Ä-C] Phenazine - Nivel de accesibilidad
- acceso abierto
- Condiciones de uso
- https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
- Repositorio
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/23459
Ver los metadatos del registro completo
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Oxidovanadium(IV) and dioxidovanadium(V) complexes of tridentate salicylaldehyde semicarbazones: Searching for prospective antitrypanosomal agentsFernández, MarianaBecco, LorenaCorreia, IsabelBenítez, JulioPiro, Oscar EnriqueEcheverría, Gustavo AlbertoMedeiros, AndreaComini, MarceloLavaggi, María LauraGonzález, MercedesCerecetto, HugoMoreno, VirtudesCosta Pessoa, JoaoGarat, BeatrizGambino, DinorahOxidovanadium(Iv) ComplexesDioxidovanadium(V) ComplexesSalicylaldehyde SemicarbazonesAntitrypanosomal2,2¡Ä-Bipyridine, Dipyrido[3,2-A: 2¡Ä,3¡Ä-C] Phenazinehttps://purl.org/becyt/ford/1.3https://purl.org/becyt/ford/1As a contribution to the identification of the relevant species for biological activity and the understanding of structure–activity relationships of [VIVO(L-2H)(NN)] antitrypanosomal complexes (NN is a bidentate polypyridyl DNA intercalator; L is a tridentate salicylaldehyde semicarbazone derivative), new [VVO2(L-2H)] complexes and [VIVO(L-2H)(NN)] complexes including bipy or dppz (dipyrido[3,2-a: 2′,3′-c]phenazine) co-ligands are prepared and characterized in the solid state and in solution. Their activity is evaluated on Trypanosoma cruzi. The lipophilicity, as structural descriptor related to bioactivity, of the whole [VIVO(L-2H)(NN)] series is determined. Furthermore, the antiproliferative effect of those new compounds showing activity against T. cruzi is evaluated on the genetically related parasite T. brucei with the aim to develop broad spectrum agents. The new [VIVO(L-2H)(dppz)] complexes are about ten to fifteen times more toxic to T. cruzi than the bipy analogues and show quite good in vitro activity on T. brucei brucei. They are shown to interact with DNA, suggesting that this biomolecule may be the parasite target. The stability of the VIVO-complexes in solution is accessed by several techniques. Globally the data suggest that the relevant species for biological activity are the [VIVO(L-2H)(NN)] compounds, their order of activity being dependent on the NN nature, but not much on the substitution on the salicylaldehyde semicarbazone moiety. A parabolic relationship between biological response and lipophilicity (determined as RM = log [(1 / Rf) − 1] by a TLC method) is obtained. From this correlation an optimum RM value, close to 1.44, was found, which may be used as design guide for future development of antitrypanosomal compounds.Fil: Fernández, Mariana. Universidad de la República; UruguayFil: Becco, Lorena. Universidad de la República; UruguayFil: Correia, Isabel. Universidade Técnica de Lisboa; PortugalFil: Benítez, Julio. Universidad de la República; UruguayFil: Piro, Oscar Enrique. 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. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Física; ArgentinaFil: Echeverría, Gustavo Alberto. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Física; Argentina. 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: Medeiros, Andrea. Universidad de la República; Uruguay. Instituto Pasteur de Montevideo; UruguayFil: Comini, Marcelo. Instituto Pasteur de Montevideo; UruguayFil: Lavaggi, María Laura. Universidad de la República; UruguayFil: González, Mercedes. Universidad de la República; UruguayFil: Cerecetto, Hugo. Universidad de la República; UruguayFil: Moreno, Virtudes. Universidad de Barcelona; EspañaFil: Costa Pessoa, Joao. Universidade Técnica de Lisboa; PortugalFil: Garat, Beatriz. Universidad de la República; UruguayFil: Gambino, Dinorah. Universidad de la República; UruguayElsevier2013-03info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/23459Fernández, Mariana; Becco, Lorena; Correia, Isabel; Benítez, Julio; Piro, Oscar Enrique; et al.; Oxidovanadium(IV) and dioxidovanadium(V) complexes of tridentate salicylaldehyde semicarbazones: Searching for prospective antitrypanosomal agents; Elsevier; Journal of Inorganic Biochemistry; 127; 3-2013; 150-1600162-0134CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.jinorgbio.2013.02.010info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0162013413000500info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:21:01Zoai:ri.conicet.gov.ar:11336/23459instacron: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 10:21:01.519CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse |
dc.title.none.fl_str_mv |
Oxidovanadium(IV) and dioxidovanadium(V) complexes of tridentate salicylaldehyde semicarbazones: Searching for prospective antitrypanosomal agents |
title |
Oxidovanadium(IV) and dioxidovanadium(V) complexes of tridentate salicylaldehyde semicarbazones: Searching for prospective antitrypanosomal agents |
spellingShingle |
Oxidovanadium(IV) and dioxidovanadium(V) complexes of tridentate salicylaldehyde semicarbazones: Searching for prospective antitrypanosomal agents Fernández, Mariana Oxidovanadium(Iv) Complexes Dioxidovanadium(V) Complexes Salicylaldehyde Semicarbazones Antitrypanosomal 2,2¡Ä-Bipyridine, Dipyrido[3,2-A: 2¡Ä,3¡Ä-C] Phenazine |
title_short |
Oxidovanadium(IV) and dioxidovanadium(V) complexes of tridentate salicylaldehyde semicarbazones: Searching for prospective antitrypanosomal agents |
title_full |
Oxidovanadium(IV) and dioxidovanadium(V) complexes of tridentate salicylaldehyde semicarbazones: Searching for prospective antitrypanosomal agents |
title_fullStr |
Oxidovanadium(IV) and dioxidovanadium(V) complexes of tridentate salicylaldehyde semicarbazones: Searching for prospective antitrypanosomal agents |
title_full_unstemmed |
Oxidovanadium(IV) and dioxidovanadium(V) complexes of tridentate salicylaldehyde semicarbazones: Searching for prospective antitrypanosomal agents |
title_sort |
Oxidovanadium(IV) and dioxidovanadium(V) complexes of tridentate salicylaldehyde semicarbazones: Searching for prospective antitrypanosomal agents |
dc.creator.none.fl_str_mv |
Fernández, Mariana Becco, Lorena Correia, Isabel Benítez, Julio Piro, Oscar Enrique Echeverría, Gustavo Alberto Medeiros, Andrea Comini, Marcelo Lavaggi, María Laura González, Mercedes Cerecetto, Hugo Moreno, Virtudes Costa Pessoa, Joao Garat, Beatriz Gambino, Dinorah |
author |
Fernández, Mariana |
author_facet |
Fernández, Mariana Becco, Lorena Correia, Isabel Benítez, Julio Piro, Oscar Enrique Echeverría, Gustavo Alberto Medeiros, Andrea Comini, Marcelo Lavaggi, María Laura González, Mercedes Cerecetto, Hugo Moreno, Virtudes Costa Pessoa, Joao Garat, Beatriz Gambino, Dinorah |
author_role |
author |
author2 |
Becco, Lorena Correia, Isabel Benítez, Julio Piro, Oscar Enrique Echeverría, Gustavo Alberto Medeiros, Andrea Comini, Marcelo Lavaggi, María Laura González, Mercedes Cerecetto, Hugo Moreno, Virtudes Costa Pessoa, Joao Garat, Beatriz Gambino, Dinorah |
author2_role |
author author author author author author author author author author author author author author |
dc.subject.none.fl_str_mv |
Oxidovanadium(Iv) Complexes Dioxidovanadium(V) Complexes Salicylaldehyde Semicarbazones Antitrypanosomal 2,2¡Ä-Bipyridine, Dipyrido[3,2-A: 2¡Ä,3¡Ä-C] Phenazine |
topic |
Oxidovanadium(Iv) Complexes Dioxidovanadium(V) Complexes Salicylaldehyde Semicarbazones Antitrypanosomal 2,2¡Ä-Bipyridine, Dipyrido[3,2-A: 2¡Ä,3¡Ä-C] Phenazine |
purl_subject.fl_str_mv |
https://purl.org/becyt/ford/1.3 https://purl.org/becyt/ford/1 |
dc.description.none.fl_txt_mv |
As a contribution to the identification of the relevant species for biological activity and the understanding of structure–activity relationships of [VIVO(L-2H)(NN)] antitrypanosomal complexes (NN is a bidentate polypyridyl DNA intercalator; L is a tridentate salicylaldehyde semicarbazone derivative), new [VVO2(L-2H)] complexes and [VIVO(L-2H)(NN)] complexes including bipy or dppz (dipyrido[3,2-a: 2′,3′-c]phenazine) co-ligands are prepared and characterized in the solid state and in solution. Their activity is evaluated on Trypanosoma cruzi. The lipophilicity, as structural descriptor related to bioactivity, of the whole [VIVO(L-2H)(NN)] series is determined. Furthermore, the antiproliferative effect of those new compounds showing activity against T. cruzi is evaluated on the genetically related parasite T. brucei with the aim to develop broad spectrum agents. The new [VIVO(L-2H)(dppz)] complexes are about ten to fifteen times more toxic to T. cruzi than the bipy analogues and show quite good in vitro activity on T. brucei brucei. They are shown to interact with DNA, suggesting that this biomolecule may be the parasite target. The stability of the VIVO-complexes in solution is accessed by several techniques. Globally the data suggest that the relevant species for biological activity are the [VIVO(L-2H)(NN)] compounds, their order of activity being dependent on the NN nature, but not much on the substitution on the salicylaldehyde semicarbazone moiety. A parabolic relationship between biological response and lipophilicity (determined as RM = log [(1 / Rf) − 1] by a TLC method) is obtained. From this correlation an optimum RM value, close to 1.44, was found, which may be used as design guide for future development of antitrypanosomal compounds. Fil: Fernández, Mariana. Universidad de la República; Uruguay Fil: Becco, Lorena. Universidad de la República; Uruguay Fil: Correia, Isabel. Universidade Técnica de Lisboa; Portugal Fil: Benítez, Julio. Universidad de la República; Uruguay Fil: Piro, Oscar Enrique. 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. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Física; Argentina Fil: Echeverría, Gustavo Alberto. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Física; Argentina. 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: Medeiros, Andrea. Universidad de la República; Uruguay. Instituto Pasteur de Montevideo; Uruguay Fil: Comini, Marcelo. Instituto Pasteur de Montevideo; Uruguay Fil: Lavaggi, María Laura. Universidad de la República; Uruguay Fil: González, Mercedes. Universidad de la República; Uruguay Fil: Cerecetto, Hugo. Universidad de la República; Uruguay Fil: Moreno, Virtudes. Universidad de Barcelona; España Fil: Costa Pessoa, Joao. Universidade Técnica de Lisboa; Portugal Fil: Garat, Beatriz. Universidad de la República; Uruguay Fil: Gambino, Dinorah. Universidad de la República; Uruguay |
description |
As a contribution to the identification of the relevant species for biological activity and the understanding of structure–activity relationships of [VIVO(L-2H)(NN)] antitrypanosomal complexes (NN is a bidentate polypyridyl DNA intercalator; L is a tridentate salicylaldehyde semicarbazone derivative), new [VVO2(L-2H)] complexes and [VIVO(L-2H)(NN)] complexes including bipy or dppz (dipyrido[3,2-a: 2′,3′-c]phenazine) co-ligands are prepared and characterized in the solid state and in solution. Their activity is evaluated on Trypanosoma cruzi. The lipophilicity, as structural descriptor related to bioactivity, of the whole [VIVO(L-2H)(NN)] series is determined. Furthermore, the antiproliferative effect of those new compounds showing activity against T. cruzi is evaluated on the genetically related parasite T. brucei with the aim to develop broad spectrum agents. The new [VIVO(L-2H)(dppz)] complexes are about ten to fifteen times more toxic to T. cruzi than the bipy analogues and show quite good in vitro activity on T. brucei brucei. They are shown to interact with DNA, suggesting that this biomolecule may be the parasite target. The stability of the VIVO-complexes in solution is accessed by several techniques. Globally the data suggest that the relevant species for biological activity are the [VIVO(L-2H)(NN)] compounds, their order of activity being dependent on the NN nature, but not much on the substitution on the salicylaldehyde semicarbazone moiety. A parabolic relationship between biological response and lipophilicity (determined as RM = log [(1 / Rf) − 1] by a TLC method) is obtained. From this correlation an optimum RM value, close to 1.44, was found, which may be used as design guide for future development of antitrypanosomal compounds. |
publishDate |
2013 |
dc.date.none.fl_str_mv |
2013-03 |
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/11336/23459 Fernández, Mariana; Becco, Lorena; Correia, Isabel; Benítez, Julio; Piro, Oscar Enrique; et al.; Oxidovanadium(IV) and dioxidovanadium(V) complexes of tridentate salicylaldehyde semicarbazones: Searching for prospective antitrypanosomal agents; Elsevier; Journal of Inorganic Biochemistry; 127; 3-2013; 150-160 0162-0134 CONICET Digital CONICET |
url |
http://hdl.handle.net/11336/23459 |
identifier_str_mv |
Fernández, Mariana; Becco, Lorena; Correia, Isabel; Benítez, Julio; Piro, Oscar Enrique; et al.; Oxidovanadium(IV) and dioxidovanadium(V) complexes of tridentate salicylaldehyde semicarbazones: Searching for prospective antitrypanosomal agents; Elsevier; Journal of Inorganic Biochemistry; 127; 3-2013; 150-160 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/doi/10.1016/j.jinorgbio.2013.02.010 info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0162013413000500 |
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 |
dc.publisher.none.fl_str_mv |
Elsevier |
publisher.none.fl_str_mv |
Elsevier |
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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1844614196196540416 |
score |
13.070432 |