Synthesis, Structure, and Biological Assays of Novel Trifluoromethyldiazepine–Metal Complexes
- Autores
- Rocha, Mariana; Echeverría, Gustavo Alberto; Piro, Oscar Enrique; Jios, Jorge Luis; Molina, Rocío Daniela Inés; Arena, Mario Eduardo; Ulic, Sonia Elizabeth; Gil, Diego Mauricio
- Año de publicación
- 2019
- Idioma
- inglés
- Tipo de recurso
- artículo
- Estado
- versión publicada
- Descripción
- A new series of CuII, NiII, CoII, and MnIII complexes have been synthesised from the (6Z)-6-(7-trifluoromethyl-1,2,3,4-tetrahydro-5H-1,4-diazepin-5-ylidene)cyclohexa-2,4-dien-1-one (HDZP) ligand. These complexes were characterised by elemental, spectroscopic (IR and UV-vis), and thermal analysis. The crystal structure of Cu-DZP was solved by X-ray diffraction methods. The complex crystallises in the monoclinic P21/c space group, with two molecules per unit cell. The crystal lattice is stabilised by different intra and intermolecular interactions. Hirshfeld surface analysis was employed to obtain additional information about interactions that are responsible for the crystal packing. Quantitative examination of the fingerprint plots indicated the dominant contribution of H⋯H and H⋯X (X = O, F) interactions in the crystal packing. In addition, C-H⋯chelate ring (CR) and C-H⋯π interactions are described in detail and evaluated using DFT calculations. The antibacterial properties and the mechanism of inhibition of the main bacterial resistant mechanism, the biofilm, of the metal complexes and free ligand were investigated. [Mn(DZP)3]·2H2O was the most active complex against the Pseudomonas aeruginosa biofilm formation with an inhibition of 40 %. However, none of the complexes inhibit more than 25 % of the Gram negative bacteria microbial development. The most meaningful result was the bactericidal effect of [Co(DZP)2(H2O)2]·2H2O against the Gram positive bacteria, Staphylococcus aureus, which inhibits the bacterial development and significantly reduces the biofilm formation at low concentration.
Fil: Rocha, Mariana. Universidad Nacional de Tucumán; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; Argentina
Fil: Echeverría, Gustavo Alberto. Facultad de Ciencias Exactas, Universidad Nacional de la Plata; 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: Piro, Oscar Enrique. Facultad de Ciencias Exactas, Universidad Nacional de la Plata; 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: Jios, Jorge Luis. Facultad de Ciencias Exactas, Universidad Nacional de la Plata; Argentina
Fil: Molina, Rocío Daniela Inés. Universidad Nacional de Tucumán; Argentina. Universidad Nacional de Tucumán. Instituto de Biotecnología Farmacéutica y Alimentaria. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Biotecnología Farmacéutica y Alimentaria; Argentina
Fil: Arena, Mario Eduardo. Universidad Nacional de Tucumán; Argentina. Universidad Nacional de Tucumán. Instituto de Biotecnología Farmacéutica y Alimentaria. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Biotecnología Farmacéutica y Alimentaria; Argentina
Fil: Ulic, Sonia Elizabeth. Facultad de Ciencias Exactas, Universidad Nacional de la Plata; Argentina. Universidad Nacional de Luján; Argentina. 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: Gil, Diego Mauricio. Universidad Nacional de Tucumán; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; Argentina - Materia
-
DIAZEPINE
METAL COMPLEXES
INTERMOLECULAR INTERACTIONS
DFT CALCULATIONS - 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:11336/119052
Ver los metadatos del registro completo
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oai:ri.conicet.gov.ar:11336/119052 |
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spelling |
Synthesis, Structure, and Biological Assays of Novel Trifluoromethyldiazepine–Metal ComplexesRocha, MarianaEcheverría, Gustavo AlbertoPiro, Oscar EnriqueJios, Jorge LuisMolina, Rocío Daniela InésArena, Mario EduardoUlic, Sonia ElizabethGil, Diego MauricioDIAZEPINEMETAL COMPLEXESINTERMOLECULAR INTERACTIONSDFT CALCULATIONShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A new series of CuII, NiII, CoII, and MnIII complexes have been synthesised from the (6Z)-6-(7-trifluoromethyl-1,2,3,4-tetrahydro-5H-1,4-diazepin-5-ylidene)cyclohexa-2,4-dien-1-one (HDZP) ligand. These complexes were characterised by elemental, spectroscopic (IR and UV-vis), and thermal analysis. The crystal structure of Cu-DZP was solved by X-ray diffraction methods. The complex crystallises in the monoclinic P21/c space group, with two molecules per unit cell. The crystal lattice is stabilised by different intra and intermolecular interactions. Hirshfeld surface analysis was employed to obtain additional information about interactions that are responsible for the crystal packing. Quantitative examination of the fingerprint plots indicated the dominant contribution of H⋯H and H⋯X (X = O, F) interactions in the crystal packing. In addition, C-H⋯chelate ring (CR) and C-H⋯π interactions are described in detail and evaluated using DFT calculations. The antibacterial properties and the mechanism of inhibition of the main bacterial resistant mechanism, the biofilm, of the metal complexes and free ligand were investigated. [Mn(DZP)3]·2H2O was the most active complex against the Pseudomonas aeruginosa biofilm formation with an inhibition of 40 %. However, none of the complexes inhibit more than 25 % of the Gram negative bacteria microbial development. The most meaningful result was the bactericidal effect of [Co(DZP)2(H2O)2]·2H2O against the Gram positive bacteria, Staphylococcus aureus, which inhibits the bacterial development and significantly reduces the biofilm formation at low concentration.Fil: Rocha, Mariana. Universidad Nacional de Tucumán; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; ArgentinaFil: Echeverría, Gustavo Alberto. Facultad de Ciencias Exactas, Universidad Nacional de la Plata; 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: Piro, Oscar Enrique. Facultad de Ciencias Exactas, Universidad Nacional de la Plata; 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: Jios, Jorge Luis. Facultad de Ciencias Exactas, Universidad Nacional de la Plata; ArgentinaFil: Molina, Rocío Daniela Inés. Universidad Nacional de Tucumán; Argentina. Universidad Nacional de Tucumán. Instituto de Biotecnología Farmacéutica y Alimentaria. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Biotecnología Farmacéutica y Alimentaria; ArgentinaFil: Arena, Mario Eduardo. Universidad Nacional de Tucumán; Argentina. Universidad Nacional de Tucumán. Instituto de Biotecnología Farmacéutica y Alimentaria. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Biotecnología Farmacéutica y Alimentaria; ArgentinaFil: Ulic, Sonia Elizabeth. Facultad de Ciencias Exactas, Universidad Nacional de la Plata; Argentina. Universidad Nacional de Luján; Argentina. 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: Gil, Diego Mauricio. Universidad Nacional de Tucumán; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; ArgentinaCsiro Publishing2019-12info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/119052Rocha, Mariana; Echeverría, Gustavo Alberto; Piro, Oscar Enrique; Jios, Jorge Luis; Molina, Rocío Daniela Inés; et al.; Synthesis, Structure, and Biological Assays of Novel Trifluoromethyldiazepine–Metal Complexes; Csiro Publishing; Australian Journal of Chemistry; 73; 1; 12-2019; 1-120004-9425CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1071/CH19352info:eu-repo/semantics/altIdentifier/url/https://www.publish.csiro.au/ch/CH19352info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:16:05Zoai:ri.conicet.gov.ar:11336/119052instacron: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 10:16:05.445CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse |
dc.title.none.fl_str_mv |
Synthesis, Structure, and Biological Assays of Novel Trifluoromethyldiazepine–Metal Complexes |
title |
Synthesis, Structure, and Biological Assays of Novel Trifluoromethyldiazepine–Metal Complexes |
spellingShingle |
Synthesis, Structure, and Biological Assays of Novel Trifluoromethyldiazepine–Metal Complexes Rocha, Mariana DIAZEPINE METAL COMPLEXES INTERMOLECULAR INTERACTIONS DFT CALCULATIONS |
title_short |
Synthesis, Structure, and Biological Assays of Novel Trifluoromethyldiazepine–Metal Complexes |
title_full |
Synthesis, Structure, and Biological Assays of Novel Trifluoromethyldiazepine–Metal Complexes |
title_fullStr |
Synthesis, Structure, and Biological Assays of Novel Trifluoromethyldiazepine–Metal Complexes |
title_full_unstemmed |
Synthesis, Structure, and Biological Assays of Novel Trifluoromethyldiazepine–Metal Complexes |
title_sort |
Synthesis, Structure, and Biological Assays of Novel Trifluoromethyldiazepine–Metal Complexes |
dc.creator.none.fl_str_mv |
Rocha, Mariana Echeverría, Gustavo Alberto Piro, Oscar Enrique Jios, Jorge Luis Molina, Rocío Daniela Inés Arena, Mario Eduardo Ulic, Sonia Elizabeth Gil, Diego Mauricio |
author |
Rocha, Mariana |
author_facet |
Rocha, Mariana Echeverría, Gustavo Alberto Piro, Oscar Enrique Jios, Jorge Luis Molina, Rocío Daniela Inés Arena, Mario Eduardo Ulic, Sonia Elizabeth Gil, Diego Mauricio |
author_role |
author |
author2 |
Echeverría, Gustavo Alberto Piro, Oscar Enrique Jios, Jorge Luis Molina, Rocío Daniela Inés Arena, Mario Eduardo Ulic, Sonia Elizabeth Gil, Diego Mauricio |
author2_role |
author author author author author author author |
dc.subject.none.fl_str_mv |
DIAZEPINE METAL COMPLEXES INTERMOLECULAR INTERACTIONS DFT CALCULATIONS |
topic |
DIAZEPINE METAL COMPLEXES INTERMOLECULAR INTERACTIONS DFT CALCULATIONS |
purl_subject.fl_str_mv |
https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 |
dc.description.none.fl_txt_mv |
A new series of CuII, NiII, CoII, and MnIII complexes have been synthesised from the (6Z)-6-(7-trifluoromethyl-1,2,3,4-tetrahydro-5H-1,4-diazepin-5-ylidene)cyclohexa-2,4-dien-1-one (HDZP) ligand. These complexes were characterised by elemental, spectroscopic (IR and UV-vis), and thermal analysis. The crystal structure of Cu-DZP was solved by X-ray diffraction methods. The complex crystallises in the monoclinic P21/c space group, with two molecules per unit cell. The crystal lattice is stabilised by different intra and intermolecular interactions. Hirshfeld surface analysis was employed to obtain additional information about interactions that are responsible for the crystal packing. Quantitative examination of the fingerprint plots indicated the dominant contribution of H⋯H and H⋯X (X = O, F) interactions in the crystal packing. In addition, C-H⋯chelate ring (CR) and C-H⋯π interactions are described in detail and evaluated using DFT calculations. The antibacterial properties and the mechanism of inhibition of the main bacterial resistant mechanism, the biofilm, of the metal complexes and free ligand were investigated. [Mn(DZP)3]·2H2O was the most active complex against the Pseudomonas aeruginosa biofilm formation with an inhibition of 40 %. However, none of the complexes inhibit more than 25 % of the Gram negative bacteria microbial development. The most meaningful result was the bactericidal effect of [Co(DZP)2(H2O)2]·2H2O against the Gram positive bacteria, Staphylococcus aureus, which inhibits the bacterial development and significantly reduces the biofilm formation at low concentration. Fil: Rocha, Mariana. Universidad Nacional de Tucumán; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; Argentina Fil: Echeverría, Gustavo Alberto. Facultad de Ciencias Exactas, Universidad Nacional de la Plata; 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: Piro, Oscar Enrique. Facultad de Ciencias Exactas, Universidad Nacional de la Plata; 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: Jios, Jorge Luis. Facultad de Ciencias Exactas, Universidad Nacional de la Plata; Argentina Fil: Molina, Rocío Daniela Inés. Universidad Nacional de Tucumán; Argentina. Universidad Nacional de Tucumán. Instituto de Biotecnología Farmacéutica y Alimentaria. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Biotecnología Farmacéutica y Alimentaria; Argentina Fil: Arena, Mario Eduardo. Universidad Nacional de Tucumán; Argentina. Universidad Nacional de Tucumán. Instituto de Biotecnología Farmacéutica y Alimentaria. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Biotecnología Farmacéutica y Alimentaria; Argentina Fil: Ulic, Sonia Elizabeth. Facultad de Ciencias Exactas, Universidad Nacional de la Plata; Argentina. Universidad Nacional de Luján; Argentina. 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: Gil, Diego Mauricio. Universidad Nacional de Tucumán; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; Argentina |
description |
A new series of CuII, NiII, CoII, and MnIII complexes have been synthesised from the (6Z)-6-(7-trifluoromethyl-1,2,3,4-tetrahydro-5H-1,4-diazepin-5-ylidene)cyclohexa-2,4-dien-1-one (HDZP) ligand. These complexes were characterised by elemental, spectroscopic (IR and UV-vis), and thermal analysis. The crystal structure of Cu-DZP was solved by X-ray diffraction methods. The complex crystallises in the monoclinic P21/c space group, with two molecules per unit cell. The crystal lattice is stabilised by different intra and intermolecular interactions. Hirshfeld surface analysis was employed to obtain additional information about interactions that are responsible for the crystal packing. Quantitative examination of the fingerprint plots indicated the dominant contribution of H⋯H and H⋯X (X = O, F) interactions in the crystal packing. In addition, C-H⋯chelate ring (CR) and C-H⋯π interactions are described in detail and evaluated using DFT calculations. The antibacterial properties and the mechanism of inhibition of the main bacterial resistant mechanism, the biofilm, of the metal complexes and free ligand were investigated. [Mn(DZP)3]·2H2O was the most active complex against the Pseudomonas aeruginosa biofilm formation with an inhibition of 40 %. However, none of the complexes inhibit more than 25 % of the Gram negative bacteria microbial development. The most meaningful result was the bactericidal effect of [Co(DZP)2(H2O)2]·2H2O against the Gram positive bacteria, Staphylococcus aureus, which inhibits the bacterial development and significantly reduces the biofilm formation at low concentration. |
publishDate |
2019 |
dc.date.none.fl_str_mv |
2019-12 |
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/11336/119052 Rocha, Mariana; Echeverría, Gustavo Alberto; Piro, Oscar Enrique; Jios, Jorge Luis; Molina, Rocío Daniela Inés; et al.; Synthesis, Structure, and Biological Assays of Novel Trifluoromethyldiazepine–Metal Complexes; Csiro Publishing; Australian Journal of Chemistry; 73; 1; 12-2019; 1-12 0004-9425 CONICET Digital CONICET |
url |
http://hdl.handle.net/11336/119052 |
identifier_str_mv |
Rocha, Mariana; Echeverría, Gustavo Alberto; Piro, Oscar Enrique; Jios, Jorge Luis; Molina, Rocío Daniela Inés; et al.; Synthesis, Structure, and Biological Assays of Novel Trifluoromethyldiazepine–Metal Complexes; Csiro Publishing; Australian Journal of Chemistry; 73; 1; 12-2019; 1-12 0004-9425 CONICET Digital CONICET |
dc.language.none.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
info:eu-repo/semantics/altIdentifier/doi/10.1071/CH19352 info:eu-repo/semantics/altIdentifier/url/https://www.publish.csiro.au/ch/CH19352 |
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 |
Csiro Publishing |
publisher.none.fl_str_mv |
Csiro Publishing |
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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1844614102141370368 |
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13.070432 |