Synthesis and Neuroprotective Properties of N‑Substituted C‑Dialkoxyphosphorylated Nitrones

Herein, we report the synthesis and neuroprotective power of some N-substituted C-(dialkoxy)phosphorylated nitrones 4a−g, by studying their ability to increase the cell viability, as well as their capacity to reduce necrosis and apoptosis. We have identified (Z)-N-tert-butyl-1- (diethoxyphosphoryl)m...

Descripción completa

Detalles Bibliográficos
Autores: Piotrowska, Dorota G., Mediavilla, Laura, Cuarental, Leticia, Głowacka, Iwona E., Marco-Contelles, José, Hadjipavlou-Litina, Dimitra, López-Muñoz, Francisco, Oset-Gasque, María Jesús
Tipo de recurso: artículo
Fecha de publicación:2019
País:España
Institución:Universidad Autónoma de Madrid
Repositorio:Biblos-e Archivo. Repositorio Institucional de la UAM
Idioma:inglés
OAI Identifier:oai:repositorio.uam.es:10486/691122
Acceso en línea:http://hdl.handle.net/10486/691122
https://dx.doi.org/10.1021/acsomega.9b00189
Access Level:acceso abierto
Palabra clave:Phosphorylated nitrones
Synthesis
Neuroprotective
Necrosis and apoptosis
Cell death
Medicina
id ES_be450eb310b9a2f22538ca2cfb122dcd
oai_identifier_str oai:repositorio.uam.es:10486/691122
network_acronym_str ES
network_name_str España
repository_id_str
spelling Synthesis and Neuroprotective Properties of N‑Substituted C‑Dialkoxyphosphorylated NitronesPiotrowska, Dorota G.Mediavilla, LauraCuarental, LeticiaGłowacka, Iwona E.Marco-Contelles, JoséHadjipavlou-Litina, DimitraLópez-Muñoz, FranciscoOset-Gasque, María JesúsPhosphorylated nitronesSynthesisNeuroprotectiveNecrosis and apoptosisCell deathMedicinaHerein, we report the synthesis and neuroprotective power of some N-substituted C-(dialkoxy)phosphorylated nitrones 4a−g, by studying their ability to increase the cell viability, as well as their capacity to reduce necrosis and apoptosis. We have identified (Z)-N-tert-butyl-1- (diethoxyphosphoryl)methanimine oxide (4e) as the most potent, nontoxic, and neuroprotective agent, with a high activity against neuronal necrotic cell death, a result that correlates very well with its great capacity for the inhibition of the superoxide production (72%), as well as with the inhibition of lipid peroxidation (62%), and the 5-lipoxygenase activity (45%) at 100 μM concentrations. Thus, nitrone 4e could be a convenient promising compound for further investigationThe synthetic part of the project was supported by the National Science Centre (grant UMO-2015/17/B/ST5/ 00076). D.H.-L. gratefully acknowledges Dr A. Leo and Biobyte Corp., 201 West 4th Street, Suite 204, Claremont, CA 91711, for free access to the C-QSAR program. J.M.-C. and M.J.O.-G. thank MINECO (Government of Spain) (SAF2015- 65586-R) and Universidad Camilo José Cela (NitroStroke project, 2015-12) for supportAmerican Chemical Society (Estados Unidos)Departamento de MedicinaFacultad de MedicinaInstituto de Investigación Sanitaria Fundación Jiménez Díaz (IIS-FJD)20192019-01-01research articlehttp://purl.org/coar/resource_type/c_2df8fbb1VoRhttp://purl.org/coar/version/c_970fb48d4fbd8a85info:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10486/691122https://dx.doi.org/10.1021/acsomega.9b00189reponame:Biblos-e Archivo. Repositorio Institucional de la UAMinstname:Universidad Autónoma de MadridInglésengopen accesshttp://purl.org/coar/access_right/c_abf2info:eu-repo/semantics/openAccessoai:repositorio.uam.es:10486/6911222026-06-23T12:46:27Z
dc.title.none.fl_str_mv Synthesis and Neuroprotective Properties of N‑Substituted C‑Dialkoxyphosphorylated Nitrones
title Synthesis and Neuroprotective Properties of N‑Substituted C‑Dialkoxyphosphorylated Nitrones
spellingShingle Synthesis and Neuroprotective Properties of N‑Substituted C‑Dialkoxyphosphorylated Nitrones
Piotrowska, Dorota G.
Phosphorylated nitrones
Synthesis
Neuroprotective
Necrosis and apoptosis
Cell death
Medicina
title_short Synthesis and Neuroprotective Properties of N‑Substituted C‑Dialkoxyphosphorylated Nitrones
title_full Synthesis and Neuroprotective Properties of N‑Substituted C‑Dialkoxyphosphorylated Nitrones
title_fullStr Synthesis and Neuroprotective Properties of N‑Substituted C‑Dialkoxyphosphorylated Nitrones
title_full_unstemmed Synthesis and Neuroprotective Properties of N‑Substituted C‑Dialkoxyphosphorylated Nitrones
title_sort Synthesis and Neuroprotective Properties of N‑Substituted C‑Dialkoxyphosphorylated Nitrones
dc.creator.none.fl_str_mv Piotrowska, Dorota G.
Mediavilla, Laura
Cuarental, Leticia
Głowacka, Iwona E.
Marco-Contelles, José
Hadjipavlou-Litina, Dimitra
López-Muñoz, Francisco
Oset-Gasque, María Jesús
author Piotrowska, Dorota G.
author_facet Piotrowska, Dorota G.
Mediavilla, Laura
Cuarental, Leticia
Głowacka, Iwona E.
Marco-Contelles, José
Hadjipavlou-Litina, Dimitra
López-Muñoz, Francisco
Oset-Gasque, María Jesús
author_role author
author2 Mediavilla, Laura
Cuarental, Leticia
Głowacka, Iwona E.
Marco-Contelles, José
Hadjipavlou-Litina, Dimitra
López-Muñoz, Francisco
Oset-Gasque, María Jesús
author2_role author
author
author
author
author
author
author
dc.contributor.none.fl_str_mv Departamento de Medicina
Facultad de Medicina
Instituto de Investigación Sanitaria Fundación Jiménez Díaz (IIS-FJD)
dc.subject.none.fl_str_mv Phosphorylated nitrones
Synthesis
Neuroprotective
Necrosis and apoptosis
Cell death
Medicina
topic Phosphorylated nitrones
Synthesis
Neuroprotective
Necrosis and apoptosis
Cell death
Medicina
description Herein, we report the synthesis and neuroprotective power of some N-substituted C-(dialkoxy)phosphorylated nitrones 4a−g, by studying their ability to increase the cell viability, as well as their capacity to reduce necrosis and apoptosis. We have identified (Z)-N-tert-butyl-1- (diethoxyphosphoryl)methanimine oxide (4e) as the most potent, nontoxic, and neuroprotective agent, with a high activity against neuronal necrotic cell death, a result that correlates very well with its great capacity for the inhibition of the superoxide production (72%), as well as with the inhibition of lipid peroxidation (62%), and the 5-lipoxygenase activity (45%) at 100 μM concentrations. Thus, nitrone 4e could be a convenient promising compound for further investigation
publishDate 2019
dc.date.none.fl_str_mv 2019
2019-01-01
dc.type.none.fl_str_mv research article
http://purl.org/coar/resource_type/c_2df8fbb1
VoR
http://purl.org/coar/version/c_970fb48d4fbd8a85
dc.type.openaire.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv http://hdl.handle.net/10486/691122
https://dx.doi.org/10.1021/acsomega.9b00189
url http://hdl.handle.net/10486/691122
https://dx.doi.org/10.1021/acsomega.9b00189
dc.language.none.fl_str_mv Inglés
eng
language_invalid_str_mv Inglés
language eng
dc.rights.none.fl_str_mv open access
http://purl.org/coar/access_right/c_abf2
dc.rights.openaire.fl_str_mv info:eu-repo/semantics/openAccess
rights_invalid_str_mv open access
http://purl.org/coar/access_right/c_abf2
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv American Chemical Society (Estados Unidos)
publisher.none.fl_str_mv American Chemical Society (Estados Unidos)
dc.source.none.fl_str_mv reponame:Biblos-e Archivo. Repositorio Institucional de la UAM
instname:Universidad Autónoma de Madrid
instname_str Universidad Autónoma de Madrid
reponame_str Biblos-e Archivo. Repositorio Institucional de la UAM
collection Biblos-e Archivo. Repositorio Institucional de la UAM
repository.name.fl_str_mv
repository.mail.fl_str_mv
_version_ 1869418272121683968
score 15,300724

Similares en LA Referencia