Potent and selective MAO-B inhibitory activity: Amino- versus nitro-3-arylcoumarin derivatives

In this study we synthesized and evaluated a new series of amino and nitro 3-arylcoumarins as hMAO-A and hMAO-B inhibitors. Compounds 2, 3, 5 and 6 presented a better activity and selectivity profile against the hMAO-B isoform (IC50 values between 2 and 6 nM) than selegiline. In general, the amino d...

ver descrição completa

Detalhes bibliográficos
Autores: Matos, M. J., Rodríguez-Enríquez, F., Vilar, S., Santana, Lourdes, Uriarte, E., Hripcsak, G., Estrada, Martín, Rodríguez-Franco, María Isabel, Viña, D.
Tipo de documento: artigo
Data de publicação:2015
País:España
Recursos:Consejo Superior de Investigaciones Científicas (CSIC)
Repositório:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/110035
Acesso em linha:http://hdl.handle.net/10261/110035
Access Level:Acceso aberto
Palavra-chave:3-Arylcoumarins
Perkin reaction
Monoamine oxidase inhibitors
PAMPA assay
ADME theoretical properties
Docking studies
id ES_2b7c7d7ecabda39b6cfd00ee07b4f787
oai_identifier_str oai:digital.csic.es:10261/110035
network_acronym_str ES
network_name_str España
repository_id_str
spelling Potent and selective MAO-B inhibitory activity: Amino- versus nitro-3-arylcoumarin derivativesMatos, M. J.Rodríguez-Enríquez, F.Vilar, S.Santana, LourdesUriarte, E.Hripcsak, G.Estrada, MartínRodríguez-Franco, María IsabelViña, D.3-ArylcoumarinsPerkin reactionMonoamine oxidase inhibitorsPAMPA assayADME theoretical propertiesDocking studiesIn this study we synthesized and evaluated a new series of amino and nitro 3-arylcoumarins as hMAO-A and hMAO-B inhibitors. Compounds 2, 3, 5 and 6 presented a better activity and selectivity profile against the hMAO-B isoform (IC50 values between 2 and 6 nM) than selegiline. In general, the amino derivatives (4-6) proved to be more selective against MAO-B than the nitro derivatives (1-3). Additionally, a theoretical study of some physicochemical properties, PAMPA and reversibility assays for the most potent derivative, and molecular docking simulations were carried out to further explain the pharmacological results, and to identify the hypothetical binding mode for the compounds inside the hMAO-B.Peer ReviewedElsevier2015201520152015info:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_6501http://hdl.handle.net/10261/110035reponame:DIGITAL.CSIC. Repositorio Institucional del CSICinstname:Consejo Superior de Investigaciones Científicas (CSIC)Inglésinfo:eu-repo/semantics/openAccessoai:digital.csic.es:10261/1100352026-05-22T06:33:51Z
dc.title.none.fl_str_mv Potent and selective MAO-B inhibitory activity: Amino- versus nitro-3-arylcoumarin derivatives
title Potent and selective MAO-B inhibitory activity: Amino- versus nitro-3-arylcoumarin derivatives
spellingShingle Potent and selective MAO-B inhibitory activity: Amino- versus nitro-3-arylcoumarin derivatives
Matos, M. J.
3-Arylcoumarins
Perkin reaction
Monoamine oxidase inhibitors
PAMPA assay
ADME theoretical properties
Docking studies
title_short Potent and selective MAO-B inhibitory activity: Amino- versus nitro-3-arylcoumarin derivatives
title_full Potent and selective MAO-B inhibitory activity: Amino- versus nitro-3-arylcoumarin derivatives
title_fullStr Potent and selective MAO-B inhibitory activity: Amino- versus nitro-3-arylcoumarin derivatives
title_full_unstemmed Potent and selective MAO-B inhibitory activity: Amino- versus nitro-3-arylcoumarin derivatives
title_sort Potent and selective MAO-B inhibitory activity: Amino- versus nitro-3-arylcoumarin derivatives
dc.creator.none.fl_str_mv Matos, M. J.
Rodríguez-Enríquez, F.
Vilar, S.
Santana, Lourdes
Uriarte, E.
Hripcsak, G.
Estrada, Martín
Rodríguez-Franco, María Isabel
Viña, D.
author Matos, M. J.
author_facet Matos, M. J.
Rodríguez-Enríquez, F.
Vilar, S.
Santana, Lourdes
Uriarte, E.
Hripcsak, G.
Estrada, Martín
Rodríguez-Franco, María Isabel
Viña, D.
author_role author
author2 Rodríguez-Enríquez, F.
Vilar, S.
Santana, Lourdes
Uriarte, E.
Hripcsak, G.
Estrada, Martín
Rodríguez-Franco, María Isabel
Viña, D.
author2_role author
author
author
author
author
author
author
author
dc.subject.none.fl_str_mv 3-Arylcoumarins
Perkin reaction
Monoamine oxidase inhibitors
PAMPA assay
ADME theoretical properties
Docking studies
topic 3-Arylcoumarins
Perkin reaction
Monoamine oxidase inhibitors
PAMPA assay
ADME theoretical properties
Docking studies
description In this study we synthesized and evaluated a new series of amino and nitro 3-arylcoumarins as hMAO-A and hMAO-B inhibitors. Compounds 2, 3, 5 and 6 presented a better activity and selectivity profile against the hMAO-B isoform (IC50 values between 2 and 6 nM) than selegiline. In general, the amino derivatives (4-6) proved to be more selective against MAO-B than the nitro derivatives (1-3). Additionally, a theoretical study of some physicochemical properties, PAMPA and reversibility assays for the most potent derivative, and molecular docking simulations were carried out to further explain the pharmacological results, and to identify the hypothetical binding mode for the compounds inside the hMAO-B.
publishDate 2015
dc.date.none.fl_str_mv 2015
2015
2015
2015
dc.type.none.fl_str_mv info:eu-repo/semantics/article
http://purl.org/coar/resource_type/c_6501
format article
dc.identifier.none.fl_str_mv http://hdl.handle.net/10261/110035
url http://hdl.handle.net/10261/110035
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv Elsevier
publisher.none.fl_str_mv Elsevier
dc.source.none.fl_str_mv reponame:DIGITAL.CSIC. Repositorio Institucional del CSIC
instname:Consejo Superior de Investigaciones Científicas (CSIC)
instname_str Consejo Superior de Investigaciones Científicas (CSIC)
reponame_str DIGITAL.CSIC. Repositorio Institucional del CSIC
collection DIGITAL.CSIC. Repositorio Institucional del CSIC
repository.name.fl_str_mv
repository.mail.fl_str_mv
_version_ 1869405147392638976
score 15.812429

Registros relacionados