Copper(II) complexes with cyanoguanidine and o-phenanthroline: Theoretical studies, in vitro antimicrobial activity and alkaline phosphatase inhibitory effect

Autores
Martínez Medina, Juan José; Islas, María Soledad; López Tévez, Libertad Leonor; Ferrer, Evelina Gloria; Okulik, Nora Beatriz; Williams, Patricia Ana María
Año de publicación
2014
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Calculations based on density functional methods are carried out for two Cu(II) complexes with cyanoguanidine (cnge) and o-phenanthroline (o-phen): [Cu(o-phen)2(cnge)](NO3)22H2O (1) and [Cu(o-phen)(cnge)(H2O)(NO3)2] (2). The calculated geometrical parameters are in agreement with the experimental values. The results of Atoms in Molecules (AIM) topological analysis of the electron density indicate that the Cu–N(phen) bonds in complex (1) have lower electron density, suggesting that those bonds are stronger in complex (2). Moreover, the ionic character of the Cu–N bond in the complex (1) is slightly stronger than that in the complex (2) and this situation would explain the fact that only complex (2) was stable in water solution. For this reason, the antimicrobial and enzymatic assays were performed using complex (2). It is well known that the increased use of antibiotics has resulted in the development of resistant bacterial and fungal strains. In this context, the study of novel antimicrobial agents has an enormous importance and metal complexes represent an interesting alternative for the treatment of infectious diseases. The aim of this work is to prove the modification of some biological properties like antimicrobial activity or alkaline phosphatase inhibitory activity upon copper complexation. The antimicrobial profile of the metal, the ligands and complex (2) was studied against several bacterial and fungal strains by different microbiological methods. The values of MIC indicate that the complexation increases the antibacterial activity against Enterococcus faecalis, but decreases this activity against Pseudomonas aeruginosa. The complex (2) exhibited longer PAEs/PAFEs than copper and o-phen against Escherichia coli and all fungal strains, and longer PAEs/PAFEs than some antibiotics or antifungal agents against E. coli, Staphylococcus aureus and Candida albicans. Complexation also improves the alkaline phosphatase inhibitory effect of copper and cnge. Therefore, the interaction of copper(II) with N-containing ligands may provide a promising strategy for the development of novel drugs with enhanced antimicrobial activity or alkaline phosphatase inhibitory activity.
Fil: Martínez Medina, Juan José. Universidad Nacional del Chaco Austral; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Islas, María Soledad. 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: López Tévez, Libertad Leonor. Universidad Nacional del Chaco Austral; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Ferrer, Evelina Gloria. 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: Okulik, Nora Beatriz. Universidad Nacional del Chaco Austral; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Williams, Patricia Ana María. 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
Materia
Phenanthroline
Cyanoguanidine
Copper Complexes
Dft Calculations
Antimicrobial Properties
Alkaline Phosphatase Specific Activity
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:11336/24981
Acceder
id CONICETDig_852bc8b3b12f35f21ca0db428333673b
oai_identifier_str oai:ri.conicet.gov.ar:11336/24981
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Copper(II) complexes with cyanoguanidine and o-phenanthroline: Theoretical studies, in vitro antimicrobial activity and alkaline phosphatase inhibitory effectMartínez Medina, Juan JoséIslas, María SoledadLópez Tévez, Libertad LeonorFerrer, Evelina GloriaOkulik, Nora BeatrizWilliams, Patricia Ana MaríaPhenanthrolineCyanoguanidineCopper ComplexesDft CalculationsAntimicrobial PropertiesAlkaline Phosphatase Specific Activityhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1https://purl.org/becyt/ford/1.6https://purl.org/becyt/ford/1Calculations based on density functional methods are carried out for two Cu(II) complexes with cyanoguanidine (cnge) and o-phenanthroline (o-phen): [Cu(o-phen)2(cnge)](NO3)22H2O (1) and [Cu(o-phen)(cnge)(H2O)(NO3)2] (2). The calculated geometrical parameters are in agreement with the experimental values. The results of Atoms in Molecules (AIM) topological analysis of the electron density indicate that the Cu–N(phen) bonds in complex (1) have lower electron density, suggesting that those bonds are stronger in complex (2). Moreover, the ionic character of the Cu–N bond in the complex (1) is slightly stronger than that in the complex (2) and this situation would explain the fact that only complex (2) was stable in water solution. For this reason, the antimicrobial and enzymatic assays were performed using complex (2). It is well known that the increased use of antibiotics has resulted in the development of resistant bacterial and fungal strains. In this context, the study of novel antimicrobial agents has an enormous importance and metal complexes represent an interesting alternative for the treatment of infectious diseases. The aim of this work is to prove the modification of some biological properties like antimicrobial activity or alkaline phosphatase inhibitory activity upon copper complexation. The antimicrobial profile of the metal, the ligands and complex (2) was studied against several bacterial and fungal strains by different microbiological methods. The values of MIC indicate that the complexation increases the antibacterial activity against Enterococcus faecalis, but decreases this activity against Pseudomonas aeruginosa. The complex (2) exhibited longer PAEs/PAFEs than copper and o-phen against Escherichia coli and all fungal strains, and longer PAEs/PAFEs than some antibiotics or antifungal agents against E. coli, Staphylococcus aureus and Candida albicans. Complexation also improves the alkaline phosphatase inhibitory effect of copper and cnge. Therefore, the interaction of copper(II) with N-containing ligands may provide a promising strategy for the development of novel drugs with enhanced antimicrobial activity or alkaline phosphatase inhibitory activity.Fil: Martínez Medina, Juan José. Universidad Nacional del Chaco Austral; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Islas, María Soledad. 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: López Tévez, Libertad Leonor. Universidad Nacional del Chaco Austral; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Ferrer, Evelina Gloria. 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: Okulik, Nora Beatriz. Universidad Nacional del Chaco Austral; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Williams, Patricia Ana María. 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"; ArgentinaElsevier Science2014-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/24981Martínez Medina, Juan José; Islas, María Soledad; López Tévez, Libertad Leonor; Ferrer, Evelina Gloria; Okulik, Nora Beatriz; et al.; Copper(II) complexes with cyanoguanidine and o-phenanthroline: Theoretical studies, in vitro antimicrobial activity and alkaline phosphatase inhibitory effect; Elsevier Science; Journal of Molecular Structure; 1058; 1-2014; 298-3070022-2860CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0022286013009654info:eu-repo/semantics/altIdentifier/doi/10.1016/j.molstruc.2013.11.014info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-10T13:05:39Zoai:ri.conicet.gov.ar:11336/24981instacron: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:34982025-09-10 13:05:40.1CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Copper(II) complexes with cyanoguanidine and o-phenanthroline: Theoretical studies, in vitro antimicrobial activity and alkaline phosphatase inhibitory effect
title Copper(II) complexes with cyanoguanidine and o-phenanthroline: Theoretical studies, in vitro antimicrobial activity and alkaline phosphatase inhibitory effect
spellingShingle Copper(II) complexes with cyanoguanidine and o-phenanthroline: Theoretical studies, in vitro antimicrobial activity and alkaline phosphatase inhibitory effect
Martínez Medina, Juan José
Phenanthroline
Cyanoguanidine
Copper Complexes
Dft Calculations
Antimicrobial Properties
Alkaline Phosphatase Specific Activity
title_short Copper(II) complexes with cyanoguanidine and o-phenanthroline: Theoretical studies, in vitro antimicrobial activity and alkaline phosphatase inhibitory effect
title_full Copper(II) complexes with cyanoguanidine and o-phenanthroline: Theoretical studies, in vitro antimicrobial activity and alkaline phosphatase inhibitory effect
title_fullStr Copper(II) complexes with cyanoguanidine and o-phenanthroline: Theoretical studies, in vitro antimicrobial activity and alkaline phosphatase inhibitory effect
title_full_unstemmed Copper(II) complexes with cyanoguanidine and o-phenanthroline: Theoretical studies, in vitro antimicrobial activity and alkaline phosphatase inhibitory effect
title_sort Copper(II) complexes with cyanoguanidine and o-phenanthroline: Theoretical studies, in vitro antimicrobial activity and alkaline phosphatase inhibitory effect
dc.creator.none.fl_str_mv Martínez Medina, Juan José
Islas, María Soledad
López Tévez, Libertad Leonor
Ferrer, Evelina Gloria
Okulik, Nora Beatriz
Williams, Patricia Ana María
author Martínez Medina, Juan José
author_facet Martínez Medina, Juan José
Islas, María Soledad
López Tévez, Libertad Leonor
Ferrer, Evelina Gloria
Okulik, Nora Beatriz
Williams, Patricia Ana María
author_role author
author2 Islas, María Soledad
López Tévez, Libertad Leonor
Ferrer, Evelina Gloria
Okulik, Nora Beatriz
Williams, Patricia Ana María
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv Phenanthroline
Cyanoguanidine
Copper Complexes
Dft Calculations
Antimicrobial Properties
Alkaline Phosphatase Specific Activity
topic Phenanthroline
Cyanoguanidine
Copper Complexes
Dft Calculations
Antimicrobial Properties
Alkaline Phosphatase Specific Activity
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
https://purl.org/becyt/ford/1.6
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Calculations based on density functional methods are carried out for two Cu(II) complexes with cyanoguanidine (cnge) and o-phenanthroline (o-phen): [Cu(o-phen)2(cnge)](NO3)22H2O (1) and [Cu(o-phen)(cnge)(H2O)(NO3)2] (2). The calculated geometrical parameters are in agreement with the experimental values. The results of Atoms in Molecules (AIM) topological analysis of the electron density indicate that the Cu–N(phen) bonds in complex (1) have lower electron density, suggesting that those bonds are stronger in complex (2). Moreover, the ionic character of the Cu–N bond in the complex (1) is slightly stronger than that in the complex (2) and this situation would explain the fact that only complex (2) was stable in water solution. For this reason, the antimicrobial and enzymatic assays were performed using complex (2). It is well known that the increased use of antibiotics has resulted in the development of resistant bacterial and fungal strains. In this context, the study of novel antimicrobial agents has an enormous importance and metal complexes represent an interesting alternative for the treatment of infectious diseases. The aim of this work is to prove the modification of some biological properties like antimicrobial activity or alkaline phosphatase inhibitory activity upon copper complexation. The antimicrobial profile of the metal, the ligands and complex (2) was studied against several bacterial and fungal strains by different microbiological methods. The values of MIC indicate that the complexation increases the antibacterial activity against Enterococcus faecalis, but decreases this activity against Pseudomonas aeruginosa. The complex (2) exhibited longer PAEs/PAFEs than copper and o-phen against Escherichia coli and all fungal strains, and longer PAEs/PAFEs than some antibiotics or antifungal agents against E. coli, Staphylococcus aureus and Candida albicans. Complexation also improves the alkaline phosphatase inhibitory effect of copper and cnge. Therefore, the interaction of copper(II) with N-containing ligands may provide a promising strategy for the development of novel drugs with enhanced antimicrobial activity or alkaline phosphatase inhibitory activity.
Fil: Martínez Medina, Juan José. Universidad Nacional del Chaco Austral; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Islas, María Soledad. 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: López Tévez, Libertad Leonor. Universidad Nacional del Chaco Austral; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Ferrer, Evelina Gloria. 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: Okulik, Nora Beatriz. Universidad Nacional del Chaco Austral; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Williams, Patricia Ana María. 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
description Calculations based on density functional methods are carried out for two Cu(II) complexes with cyanoguanidine (cnge) and o-phenanthroline (o-phen): [Cu(o-phen)2(cnge)](NO3)22H2O (1) and [Cu(o-phen)(cnge)(H2O)(NO3)2] (2). The calculated geometrical parameters are in agreement with the experimental values. The results of Atoms in Molecules (AIM) topological analysis of the electron density indicate that the Cu–N(phen) bonds in complex (1) have lower electron density, suggesting that those bonds are stronger in complex (2). Moreover, the ionic character of the Cu–N bond in the complex (1) is slightly stronger than that in the complex (2) and this situation would explain the fact that only complex (2) was stable in water solution. For this reason, the antimicrobial and enzymatic assays were performed using complex (2). It is well known that the increased use of antibiotics has resulted in the development of resistant bacterial and fungal strains. In this context, the study of novel antimicrobial agents has an enormous importance and metal complexes represent an interesting alternative for the treatment of infectious diseases. The aim of this work is to prove the modification of some biological properties like antimicrobial activity or alkaline phosphatase inhibitory activity upon copper complexation. The antimicrobial profile of the metal, the ligands and complex (2) was studied against several bacterial and fungal strains by different microbiological methods. The values of MIC indicate that the complexation increases the antibacterial activity against Enterococcus faecalis, but decreases this activity against Pseudomonas aeruginosa. The complex (2) exhibited longer PAEs/PAFEs than copper and o-phen against Escherichia coli and all fungal strains, and longer PAEs/PAFEs than some antibiotics or antifungal agents against E. coli, Staphylococcus aureus and Candida albicans. Complexation also improves the alkaline phosphatase inhibitory effect of copper and cnge. Therefore, the interaction of copper(II) with N-containing ligands may provide a promising strategy for the development of novel drugs with enhanced antimicrobial activity or alkaline phosphatase inhibitory activity.
publishDate 2014
dc.date.none.fl_str_mv 2014-01
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/11336/24981
Martínez Medina, Juan José; Islas, María Soledad; López Tévez, Libertad Leonor; Ferrer, Evelina Gloria; Okulik, Nora Beatriz; et al.; Copper(II) complexes with cyanoguanidine and o-phenanthroline: Theoretical studies, in vitro antimicrobial activity and alkaline phosphatase inhibitory effect; Elsevier Science; Journal of Molecular Structure; 1058; 1-2014; 298-307
0022-2860
CONICET Digital
CONICET
url http://hdl.handle.net/11336/24981
identifier_str_mv Martínez Medina, Juan José; Islas, María Soledad; López Tévez, Libertad Leonor; Ferrer, Evelina Gloria; Okulik, Nora Beatriz; et al.; Copper(II) complexes with cyanoguanidine and o-phenanthroline: Theoretical studies, in vitro antimicrobial activity and alkaline phosphatase inhibitory effect; Elsevier Science; Journal of Molecular Structure; 1058; 1-2014; 298-307
0022-2860
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0022286013009654
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.molstruc.2013.11.014
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
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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
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dc.publisher.none.fl_str_mv Elsevier Science
publisher.none.fl_str_mv Elsevier Science
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repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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