Platinum (II) and palladium (II) complexes with (N,N') and (C,N,N') ligands derived from pyrazole as anticancer and antimalarial agents: synthesis, characterization and in vitro activities

The study of the reactivity of three 1-(2-dimethylaminoethyl)-1H-pyrazole derivatives of general formula [1-(CH2)2NMe2}-3,5-R2-pzol] {where pzol represents pyrazole and Rdouble bond; length as m-dashH (1a), Me (1b) or Ph (1c)} with [MCl2(DMSO)2] (Mdouble bond; length as m-dashPt or Pd) under differe...

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Autores: Quirante Serrano, Josefina, Ruiz, Daniel, González Gazulla, Asensio, López Martínez, Ma. Concepción, Cascante i Serratosa, Marta, Cortés Giràldez, Roldàn, Messeguer i Peypoch, Ramon, Calvis, Carme, Baldomà Llavinés, Laura, Pradines, Bruno, Pascal, Aurélie, Guérardel, Yann, Font Bardia, Ma. Mercedes, Calvet Pallàs, Maria Teresa, Biot, Christophe
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2011
País:España
Institución:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
Repositorio:Recercat. Dipósit de la Recerca de Catalunya
OAI Identifier:oai:recercat.cat:2445/49383
Acceso en línea:https://hdl.handle.net/2445/49383
Access Level:acceso abierto
Palabra clave:Càncer
Malària
Pal·ladi (Element químic)
Platí
Cancer
Malaria
Palladium
Platinum
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network_name_str España
repository_id_str
spelling Platinum (II) and palladium (II) complexes with (N,N') and (C,N,N') ligands derived from pyrazole as anticancer and antimalarial agents: synthesis, characterization and in vitro activitiesQuirante Serrano, JosefinaRuiz, DanielGonzález Gazulla, AsensioLópez Martínez, Ma. ConcepciónCascante i Serratosa, MartaCortés Giràldez, RoldànMesseguer i Peypoch, RamonCalvis, CarmeBaldomà Llavinés, LauraPradines, BrunoPascal, AurélieGuérardel, YannFont Bardia, Ma. MercedesCalvet Pallàs, Maria TeresaBiot, ChristopheCàncerMalàriaPal·ladi (Element químic)PlatíCancerMalariaPalladiumPlatinumThe study of the reactivity of three 1-(2-dimethylaminoethyl)-1H-pyrazole derivatives of general formula [1-(CH2)2NMe2}-3,5-R2-pzol] {where pzol represents pyrazole and Rdouble bond; length as m-dashH (1a), Me (1b) or Ph (1c)} with [MCl2(DMSO)2] (Mdouble bond; length as m-dashPt or Pd) under different experimental conditions allowed us to isolate and characterize cis-[M{κ2-N,N′-{[1-(CH2)2NMe2}-3,5-R2-pzol])}Cl2] {MMdouble bond; length as m-dashPtPt (2a-2c) or Pd (3a-3c)} and two cyclometallated complexes [M{κ3-C,N,N′-{[1-(CH2)2NMe2}-3-(C5H4)-5-Ph-pzol])}Cl] {Mdouble bond; length as m-dashPt(II) (4c) or Pd(II) (5c)}. Compounds 4c and 5c arise from the orthometallation of the 3-phenyl ring of ligand 1c. Complex 2a has been further characterized by X-ray crystallography. Ligands and complexes were evaluated for their in vitro antimalarial against Plasmodium falciparum and cytotoxic activities against lung (A549) and breast (MDA MB231 and MCF7) cancer cellular lines. Complexes 2a-2c and 5c exhibited only moderate antimalarial activities against two P. falciparum strains (3D7 and W2). Interestingly, cytotoxicity assays revealed that the platinacycle 4c exhibits a higher toxicity than cisplatin in the three human cell lines and that the complex 2a presents a remarkable cytotoxicity and selectivity in lung (IC50 = 3 μM) versus breast cancer cell lines (IC50 > 20 μM). Thus, complexes 2c and 4c appear to be promising leads, creating a novel family of anticancer agents. Electrophoretic DNA migration studies in presence of the synthesized compounds have been performed, in order to get further insights into their mechanism of action.Elsevier B.V.2014201420112014info:eu-repo/semantics/articleinfo:eu-repo/semantics/acceptedVersion9 p.application/pdfhttps://hdl.handle.net/2445/49383Articles publicats en revistes (Química Inorgànica i Orgànica)reponame:Recercat. Dipósit de la Recerca de Catalunyainstname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)InglésVersió postprint del document publicat a: http://dx.doi.org/10.1016/j.jinorgbio.2011.09.021Journal of Inorganic Biochemistry, 2011, vol. 105, num. 12, p. 1720-1728http://dx.doi.org/10.1016/j.jinorgbio.2011.09.021(c) Elsevier B.V., 2011info:eu-repo/semantics/openAccessoai:recercat.cat:2445/493832026-05-29T05:05:01Z
dc.title.none.fl_str_mv Platinum (II) and palladium (II) complexes with (N,N') and (C,N,N') ligands derived from pyrazole as anticancer and antimalarial agents: synthesis, characterization and in vitro activities
title Platinum (II) and palladium (II) complexes with (N,N') and (C,N,N') ligands derived from pyrazole as anticancer and antimalarial agents: synthesis, characterization and in vitro activities
spellingShingle Platinum (II) and palladium (II) complexes with (N,N') and (C,N,N') ligands derived from pyrazole as anticancer and antimalarial agents: synthesis, characterization and in vitro activities
Quirante Serrano, Josefina
Càncer
Malària
Pal·ladi (Element químic)
Platí
Cancer
Malaria
Palladium
Platinum
title_short Platinum (II) and palladium (II) complexes with (N,N') and (C,N,N') ligands derived from pyrazole as anticancer and antimalarial agents: synthesis, characterization and in vitro activities
title_full Platinum (II) and palladium (II) complexes with (N,N') and (C,N,N') ligands derived from pyrazole as anticancer and antimalarial agents: synthesis, characterization and in vitro activities
title_fullStr Platinum (II) and palladium (II) complexes with (N,N') and (C,N,N') ligands derived from pyrazole as anticancer and antimalarial agents: synthesis, characterization and in vitro activities
title_full_unstemmed Platinum (II) and palladium (II) complexes with (N,N') and (C,N,N') ligands derived from pyrazole as anticancer and antimalarial agents: synthesis, characterization and in vitro activities
title_sort Platinum (II) and palladium (II) complexes with (N,N') and (C,N,N') ligands derived from pyrazole as anticancer and antimalarial agents: synthesis, characterization and in vitro activities
dc.creator.none.fl_str_mv Quirante Serrano, Josefina
Ruiz, Daniel
González Gazulla, Asensio
López Martínez, Ma. Concepción
Cascante i Serratosa, Marta
Cortés Giràldez, Roldàn
Messeguer i Peypoch, Ramon
Calvis, Carme
Baldomà Llavinés, Laura
Pradines, Bruno
Pascal, Aurélie
Guérardel, Yann
Font Bardia, Ma. Mercedes
Calvet Pallàs, Maria Teresa
Biot, Christophe
author Quirante Serrano, Josefina
author_facet Quirante Serrano, Josefina
Ruiz, Daniel
González Gazulla, Asensio
López Martínez, Ma. Concepción
Cascante i Serratosa, Marta
Cortés Giràldez, Roldàn
Messeguer i Peypoch, Ramon
Calvis, Carme
Baldomà Llavinés, Laura
Pradines, Bruno
Pascal, Aurélie
Guérardel, Yann
Font Bardia, Ma. Mercedes
Calvet Pallàs, Maria Teresa
Biot, Christophe
author_role author
author2 Ruiz, Daniel
González Gazulla, Asensio
López Martínez, Ma. Concepción
Cascante i Serratosa, Marta
Cortés Giràldez, Roldàn
Messeguer i Peypoch, Ramon
Calvis, Carme
Baldomà Llavinés, Laura
Pradines, Bruno
Pascal, Aurélie
Guérardel, Yann
Font Bardia, Ma. Mercedes
Calvet Pallàs, Maria Teresa
Biot, Christophe
author2_role author
author
author
author
author
author
author
author
author
author
author
author
author
author
dc.subject.none.fl_str_mv Càncer
Malària
Pal·ladi (Element químic)
Platí
Cancer
Malaria
Palladium
Platinum
topic Càncer
Malària
Pal·ladi (Element químic)
Platí
Cancer
Malaria
Palladium
Platinum
description The study of the reactivity of three 1-(2-dimethylaminoethyl)-1H-pyrazole derivatives of general formula [1-(CH2)2NMe2}-3,5-R2-pzol] {where pzol represents pyrazole and Rdouble bond; length as m-dashH (1a), Me (1b) or Ph (1c)} with [MCl2(DMSO)2] (Mdouble bond; length as m-dashPt or Pd) under different experimental conditions allowed us to isolate and characterize cis-[M{κ2-N,N′-{[1-(CH2)2NMe2}-3,5-R2-pzol])}Cl2] {MMdouble bond; length as m-dashPtPt (2a-2c) or Pd (3a-3c)} and two cyclometallated complexes [M{κ3-C,N,N′-{[1-(CH2)2NMe2}-3-(C5H4)-5-Ph-pzol])}Cl] {Mdouble bond; length as m-dashPt(II) (4c) or Pd(II) (5c)}. Compounds 4c and 5c arise from the orthometallation of the 3-phenyl ring of ligand 1c. Complex 2a has been further characterized by X-ray crystallography. Ligands and complexes were evaluated for their in vitro antimalarial against Plasmodium falciparum and cytotoxic activities against lung (A549) and breast (MDA MB231 and MCF7) cancer cellular lines. Complexes 2a-2c and 5c exhibited only moderate antimalarial activities against two P. falciparum strains (3D7 and W2). Interestingly, cytotoxicity assays revealed that the platinacycle 4c exhibits a higher toxicity than cisplatin in the three human cell lines and that the complex 2a presents a remarkable cytotoxicity and selectivity in lung (IC50 = 3 μM) versus breast cancer cell lines (IC50 > 20 μM). Thus, complexes 2c and 4c appear to be promising leads, creating a novel family of anticancer agents. Electrophoretic DNA migration studies in presence of the synthesized compounds have been performed, in order to get further insights into their mechanism of action.
publishDate 2011
dc.date.none.fl_str_mv 2011
2014
2014
2014
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/acceptedVersion
format article
status_str acceptedVersion
dc.identifier.none.fl_str_mv https://hdl.handle.net/2445/49383
url https://hdl.handle.net/2445/49383
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv Versió postprint del document publicat a: http://dx.doi.org/10.1016/j.jinorgbio.2011.09.021
Journal of Inorganic Biochemistry, 2011, vol. 105, num. 12, p. 1720-1728
http://dx.doi.org/10.1016/j.jinorgbio.2011.09.021
dc.rights.none.fl_str_mv (c) Elsevier B.V., 2011
info:eu-repo/semantics/openAccess
rights_invalid_str_mv (c) Elsevier B.V., 2011
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 9 p.
application/pdf
dc.publisher.none.fl_str_mv Elsevier B.V.
publisher.none.fl_str_mv Elsevier B.V.
dc.source.none.fl_str_mv Articles publicats en revistes (Química Inorgànica i Orgànica)
reponame:Recercat. Dipósit de la Recerca de Catalunya
instname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
instname_str Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
reponame_str Recercat. Dipósit de la Recerca de Catalunya
collection Recercat. Dipósit de la Recerca de Catalunya
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15.812429

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