A hybrid of 1-deoxynojirimycin and benzotriazole induces preferential inhibition of butyrylcholinesterase (BuChE) over acetylcholinesterase (AChE).

The synthesis of four heterodimers in which the copper(I)-catalysed azide-alkyne cycloaddition wasemployed to connect a 1-deoxynojirimycin moiety with a benzotriazole scaffold is reported. The hetero-dimers were investigated as inhibitors against acetylcholinesterase (AChE) and butyrylcholinesterase...

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Autores: Evangelista, Tereza Cristina Santos, López López, Óscar, Puerta, Adrián, Fernandes, Miguel X., Ferreira, Sabrina Baptista, Fernández-Bolaños Guzmán, José María, Lindback, Emil
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2022
País:España
Institución:Universidad de Sevilla (US)
Repositorio:idUS. Depósito de Investigación de la Universidad de Sevilla
OAI Identifier:oai:idus.us.es:11441/146884
Acceso en línea:https://hdl.handle.net/11441/146884
https://doi.org/10.1080/14756366.2022.2117912
Access Level:acceso abierto
Palabra clave:Iminosugars
Inhibitors
Cholinesterases
Alzheimer’s disease
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spelling A hybrid of 1-deoxynojirimycin and benzotriazole induces preferential inhibition of butyrylcholinesterase (BuChE) over acetylcholinesterase (AChE).Evangelista, Tereza Cristina SantosLópez López, ÓscarPuerta, AdriánFernandes, Miguel X.Ferreira, Sabrina BaptistaFernández-Bolaños Guzmán, José MaríaLindback, EmilIminosugarsInhibitorsCholinesterasesAlzheimer’s diseaseThe synthesis of four heterodimers in which the copper(I)-catalysed azide-alkyne cycloaddition wasemployed to connect a 1-deoxynojirimycin moiety with a benzotriazole scaffold is reported. The hetero-dimers were investigated as inhibitors against acetylcholinesterase (AChE) and butyrylcholinesterase(BuChE). The heterodimers displayed preferential inhibition (>9) of BuChE over AChE in the micromolarconcentration range (IC50¼7–50mM). For the most potent inhibitor of BuChE, Cornish-Bowden plots wereused, which demonstrated that it behaves as a mixed inhibitor. Modelling studies of the same inhibitordemonstrated that the benzotriazole and 1-deoxynojirimycin moiety is accommodated in the peripheralanionic site and catalytic anionic site, respectively, of AChE. The binding mode to BuChE was different asthe benzotriazole moiety is accommodated in the catalytic anionic site.Gobierno de España (MCIN/AEI) - D2020-116460RB-I00Junta de Andalucía - FQM-134Taylor and Francis GroupQuímica OrgánicaFQM134: Química Fina de CarbohidratosMinisterio de Ciencia e Innovación (MICIN). EspañaAgencia Estatal de Investigación. EspañaJunta de Andalucía2022info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionapplication/pdfapplication/pdfhttps://hdl.handle.net/11441/146884https://doi.org/10.1080/14756366.2022.2117912reponame:idUS. Depósito de Investigación de la Universidad de Sevillainstname:Universidad de Sevilla (US)InglésJournal of Enzyme Inhibition and Medicinal Chemistry, 37 (1), 2395-2402.D2020-116460RB-I00FQM-134https://doi.org/10.1080/14756366.2022.2117912info:eu-repo/semantics/openAccessoai:idus.us.es:11441/1468842026-06-17T12:51:07Z
dc.title.none.fl_str_mv A hybrid of 1-deoxynojirimycin and benzotriazole induces preferential inhibition of butyrylcholinesterase (BuChE) over acetylcholinesterase (AChE).
title A hybrid of 1-deoxynojirimycin and benzotriazole induces preferential inhibition of butyrylcholinesterase (BuChE) over acetylcholinesterase (AChE).
spellingShingle A hybrid of 1-deoxynojirimycin and benzotriazole induces preferential inhibition of butyrylcholinesterase (BuChE) over acetylcholinesterase (AChE).
Evangelista, Tereza Cristina Santos
Iminosugars
Inhibitors
Cholinesterases
Alzheimer’s disease
title_short A hybrid of 1-deoxynojirimycin and benzotriazole induces preferential inhibition of butyrylcholinesterase (BuChE) over acetylcholinesterase (AChE).
title_full A hybrid of 1-deoxynojirimycin and benzotriazole induces preferential inhibition of butyrylcholinesterase (BuChE) over acetylcholinesterase (AChE).
title_fullStr A hybrid of 1-deoxynojirimycin and benzotriazole induces preferential inhibition of butyrylcholinesterase (BuChE) over acetylcholinesterase (AChE).
title_full_unstemmed A hybrid of 1-deoxynojirimycin and benzotriazole induces preferential inhibition of butyrylcholinesterase (BuChE) over acetylcholinesterase (AChE).
title_sort A hybrid of 1-deoxynojirimycin and benzotriazole induces preferential inhibition of butyrylcholinesterase (BuChE) over acetylcholinesterase (AChE).
dc.creator.none.fl_str_mv Evangelista, Tereza Cristina Santos
López López, Óscar
Puerta, Adrián
Fernandes, Miguel X.
Ferreira, Sabrina Baptista
Fernández-Bolaños Guzmán, José María
Lindback, Emil
author Evangelista, Tereza Cristina Santos
author_facet Evangelista, Tereza Cristina Santos
López López, Óscar
Puerta, Adrián
Fernandes, Miguel X.
Ferreira, Sabrina Baptista
Fernández-Bolaños Guzmán, José María
Lindback, Emil
author_role author
author2 López López, Óscar
Puerta, Adrián
Fernandes, Miguel X.
Ferreira, Sabrina Baptista
Fernández-Bolaños Guzmán, José María
Lindback, Emil
author2_role author
author
author
author
author
author
dc.contributor.none.fl_str_mv Química Orgánica
FQM134: Química Fina de Carbohidratos
Ministerio de Ciencia e Innovación (MICIN). España
Agencia Estatal de Investigación. España
Junta de Andalucía
dc.subject.none.fl_str_mv Iminosugars
Inhibitors
Cholinesterases
Alzheimer’s disease
topic Iminosugars
Inhibitors
Cholinesterases
Alzheimer’s disease
description The synthesis of four heterodimers in which the copper(I)-catalysed azide-alkyne cycloaddition wasemployed to connect a 1-deoxynojirimycin moiety with a benzotriazole scaffold is reported. The hetero-dimers were investigated as inhibitors against acetylcholinesterase (AChE) and butyrylcholinesterase(BuChE). The heterodimers displayed preferential inhibition (>9) of BuChE over AChE in the micromolarconcentration range (IC50¼7–50mM). For the most potent inhibitor of BuChE, Cornish-Bowden plots wereused, which demonstrated that it behaves as a mixed inhibitor. Modelling studies of the same inhibitordemonstrated that the benzotriazole and 1-deoxynojirimycin moiety is accommodated in the peripheralanionic site and catalytic anionic site, respectively, of AChE. The binding mode to BuChE was different asthe benzotriazole moiety is accommodated in the catalytic anionic site.
publishDate 2022
dc.date.none.fl_str_mv 2022
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv https://hdl.handle.net/11441/146884
https://doi.org/10.1080/14756366.2022.2117912
url https://hdl.handle.net/11441/146884
https://doi.org/10.1080/14756366.2022.2117912
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv Journal of Enzyme Inhibition and Medicinal Chemistry, 37 (1), 2395-2402.
D2020-116460RB-I00
FQM-134
https://doi.org/10.1080/14756366.2022.2117912
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Taylor and Francis Group
publisher.none.fl_str_mv Taylor and Francis Group
dc.source.none.fl_str_mv reponame:idUS. Depósito de Investigación de la Universidad de Sevilla
instname:Universidad de Sevilla (US)
instname_str Universidad de Sevilla (US)
reponame_str idUS. Depósito de Investigación de la Universidad de Sevilla
collection idUS. Depósito de Investigación de la Universidad de Sevilla
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,301629

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