Evaluation of the antioxidant and neuroprotectant activities of new asymmetrical 1,3-diketones

A series of fourteen new asymmetrical 1,3-diketone derivatives have been synthesized and evaluated in the ABTS, FRAP and DPPH assays as a new chemotype with antioxidant and drug-like properties. All the compounds displayed low cytotoxicity in comparison to curcumin against the human neuroblastoma SH...

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Autores: Nieto Gómez, Carla Isabel, Comago, María del Pilar, Sanz del Castillo, Dionisia, Claramunt, Rosa M., Torralba, María del Carmen, Torres, M. Rosario, Martínez Casanova, Diana, Sánchez Alegre, Yaiza Rebeca, Escudero, Esther, Lavandera, José Luis, Cabildo, Pilar
Tipo de recurso: artículo
Fecha de publicación:2018
País:España
Institución:Universidad Nacional de Educación a Distancia
Repositorio:e-spacio. Repositorio Institucional de la UNED
Idioma:español
OAI Identifier:oai:e-spacio.uned.es:20.500.14468/23584
Acceso en línea:https://hdl.handle.net/20.500.14468/23584
Access Level:acceso abierto
Palabra clave:23 Química
neurodegeneration
oxidative stress
neuroprotectant
antioxidant
β-diketones
drug-like properties
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spelling Evaluation of the antioxidant and neuroprotectant activities of new asymmetrical 1,3-diketonesNieto Gómez, Carla IsabelComago, María del PilarSanz del Castillo, DionisiaClaramunt, Rosa M.Torralba, María del CarmenTorres, M. RosarioMartínez Casanova, DianaSánchez Alegre, Yaiza RebecaEscudero, EstherLavandera, José LuisCabildo, PilarClaramunt, Rosa M.23 Químicaneurodegenerationoxidative stressneuroprotectantantioxidantβ-diketonesdrug-like propertiesA series of fourteen new asymmetrical 1,3-diketone derivatives have been synthesized and evaluated in the ABTS, FRAP and DPPH assays as a new chemotype with antioxidant and drug-like properties. All the compounds displayed low cytotoxicity in comparison to curcumin against the human neuroblastoma SH-SY5Y cell line. Among them, (3Z,5E)-6-(2,5-difluoro-4-hydroxy-phenyl)-1,1,1-trifluoro-4-hydroxyhexa-3,5-dien-2-one (6b) and (3Z,5E)-6-(2,3-difluoro-4-hydroxy-phenyl)-1,1,1-trifluoro-4-hydroxyhexa-3,5-dien-2-one (7b) with excellent solubility and chemical stability in biorelevant media, have also shown a similar Fe+2 chelation behavior to that of curcumin. Additionally, both derivatives 6b and 7b have afforded good neuroprotection activity against H2O2 induced oxidative stress in the same neuronal cell line, with a significant reduction of intracellular ROS levels, in parallel with a good recovery of the Mitochondrial Membrane Potential (ΔΨm). Compounds 6b and 7b with a promising antioxidant and drug-like profile, with low cytotoxic and good neuroprotectant activity, constitute a new interesting chemical class with high potential as new therapeutic agents against neurodegenerative diseases.MDPIhttps://orcid.org/0000-0002-9682-1238e-Spacio UNED20242024-08-3020182018-07-2420182018-07-24journal articlehttp://purl.org/coar/resource_type/c_6501info:eu-repo/semantics/articleapplication/pdfhttps://hdl.handle.net/20.500.14468/23584reponame:e-spacio. Repositorio Institucional de la UNEDinstname:Universidad Nacional de Educación a DistanciaEspañolspaopen accesshttp://purl.org/coar/access_right/c_abf2info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-nd/4.0/deed.esoai:e-spacio.uned.es:20.500.14468/235842026-06-06T12:38:31Z
dc.title.none.fl_str_mv Evaluation of the antioxidant and neuroprotectant activities of new asymmetrical 1,3-diketones
title Evaluation of the antioxidant and neuroprotectant activities of new asymmetrical 1,3-diketones
spellingShingle Evaluation of the antioxidant and neuroprotectant activities of new asymmetrical 1,3-diketones
Nieto Gómez, Carla Isabel
23 Química
neurodegeneration
oxidative stress
neuroprotectant
antioxidant
β-diketones
drug-like properties
title_short Evaluation of the antioxidant and neuroprotectant activities of new asymmetrical 1,3-diketones
title_full Evaluation of the antioxidant and neuroprotectant activities of new asymmetrical 1,3-diketones
title_fullStr Evaluation of the antioxidant and neuroprotectant activities of new asymmetrical 1,3-diketones
title_full_unstemmed Evaluation of the antioxidant and neuroprotectant activities of new asymmetrical 1,3-diketones
title_sort Evaluation of the antioxidant and neuroprotectant activities of new asymmetrical 1,3-diketones
dc.creator.none.fl_str_mv Nieto Gómez, Carla Isabel
Comago, María del Pilar
Sanz del Castillo, Dionisia
Claramunt, Rosa M.
Torralba, María del Carmen
Torres, M. Rosario
Martínez Casanova, Diana
Sánchez Alegre, Yaiza Rebeca
Escudero, Esther
Lavandera, José Luis
Cabildo, Pilar
Claramunt, Rosa M.
author Nieto Gómez, Carla Isabel
author_facet Nieto Gómez, Carla Isabel
Comago, María del Pilar
Sanz del Castillo, Dionisia
Claramunt, Rosa M.
Torralba, María del Carmen
Torres, M. Rosario
Martínez Casanova, Diana
Sánchez Alegre, Yaiza Rebeca
Escudero, Esther
Lavandera, José Luis
Cabildo, Pilar
author_role author
author2 Comago, María del Pilar
Sanz del Castillo, Dionisia
Claramunt, Rosa M.
Torralba, María del Carmen
Torres, M. Rosario
Martínez Casanova, Diana
Sánchez Alegre, Yaiza Rebeca
Escudero, Esther
Lavandera, José Luis
Cabildo, Pilar
author2_role author
author
author
author
author
author
author
author
author
author
dc.contributor.none.fl_str_mv https://orcid.org/0000-0002-9682-1238
e-Spacio UNED
dc.subject.none.fl_str_mv 23 Química
neurodegeneration
oxidative stress
neuroprotectant
antioxidant
β-diketones
drug-like properties
topic 23 Química
neurodegeneration
oxidative stress
neuroprotectant
antioxidant
β-diketones
drug-like properties
description A series of fourteen new asymmetrical 1,3-diketone derivatives have been synthesized and evaluated in the ABTS, FRAP and DPPH assays as a new chemotype with antioxidant and drug-like properties. All the compounds displayed low cytotoxicity in comparison to curcumin against the human neuroblastoma SH-SY5Y cell line. Among them, (3Z,5E)-6-(2,5-difluoro-4-hydroxy-phenyl)-1,1,1-trifluoro-4-hydroxyhexa-3,5-dien-2-one (6b) and (3Z,5E)-6-(2,3-difluoro-4-hydroxy-phenyl)-1,1,1-trifluoro-4-hydroxyhexa-3,5-dien-2-one (7b) with excellent solubility and chemical stability in biorelevant media, have also shown a similar Fe+2 chelation behavior to that of curcumin. Additionally, both derivatives 6b and 7b have afforded good neuroprotection activity against H2O2 induced oxidative stress in the same neuronal cell line, with a significant reduction of intracellular ROS levels, in parallel with a good recovery of the Mitochondrial Membrane Potential (ΔΨm). Compounds 6b and 7b with a promising antioxidant and drug-like profile, with low cytotoxic and good neuroprotectant activity, constitute a new interesting chemical class with high potential as new therapeutic agents against neurodegenerative diseases.
publishDate 2018
dc.date.none.fl_str_mv 2018
2018-07-24
2018
2018-07-24
2024
2024-08-30
dc.type.none.fl_str_mv journal article
http://purl.org/coar/resource_type/c_6501
dc.type.openaire.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv https://hdl.handle.net/20.500.14468/23584
url https://hdl.handle.net/20.500.14468/23584
dc.language.none.fl_str_mv Español
spa
language_invalid_str_mv Español
language spa
dc.rights.none.fl_str_mv open access
http://purl.org/coar/access_right/c_abf2
info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-nd/4.0/deed.es
rights_invalid_str_mv open access
http://purl.org/coar/access_right/c_abf2
https://creativecommons.org/licenses/by-nc-nd/4.0/deed.es
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv MDPI
publisher.none.fl_str_mv MDPI
dc.source.none.fl_str_mv reponame:e-spacio. Repositorio Institucional de la UNED
instname:Universidad Nacional de Educación a Distancia
instname_str Universidad Nacional de Educación a Distancia
reponame_str e-spacio. Repositorio Institucional de la UNED
collection e-spacio. Repositorio Institucional de la UNED
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,812429

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