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
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/23459
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/23459
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling 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 Técnicas2025-10-22T11:53:43Zoai: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:34982025-10-22 11:53:43.699CONICET 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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score 12.982451

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