Inhibition of β-carbonic anhydrases from Brucella suis with C-cinnamoyl glycosides incorporating the phenol moiety

Autores
Riafrecha, Leonardo Ezequiel; Vullo, Daniela; Ouahrani Bettache, Safia; Köhler, Stephan; Dumy, Pascal; Winum, Jean Yves; Supuran, Claudiu T.; Colinas, Pedro Alfonso
Año de publicación
2015
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A small series of C-glycosides containing the phenol moiety was tested for the inhibition of the β-class carbonic anhydrases (βCAs, EC 4.2.1.1) from Brucella suis. Many compounds showed activities in the micromolar or submicromolar range and excellent selectivity for pathogen CAs over human isozymes. Glycosides incorporating the 3-hydroxyphenyl moiety showed the best inhibition profile, and therefore this functionality represents lead for the development of novel anti-infectives with a new mechanism of action.
Fil: Riafrecha, Leonardo Ezequiel. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Estudio de Compuestos Orgánicos; Argentina
Fil: Vullo, Daniela. Universita Degli Studi Di Firenze; Italia
Fil: Ouahrani Bettache, Safia. Université Montpellier; Francia
Fil: Köhler, Stephan. Université Montpellier; Francia
Fil: Dumy, Pascal. Ecole Nationale Supérieure de Chimie de Montpellier; Francia
Fil: Winum, Jean Yves. Ecole Nationale Supérieure de Chimie de Montpellier; Francia
Fil: Supuran, Claudiu T.. Universita Degli Studi Di Firenze; Italia
Fil: Colinas, Pedro Alfonso. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Estudio de Compuestos Orgánicos; Argentina
Materia
ANTIBACTERIAL
CARBOHYDRATE
CARBONIC ANHYDRASE
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/39664
Acceder
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network_name_str CONICET Digital (CONICET)
spelling Inhibition of β-carbonic anhydrases from Brucella suis with C-cinnamoyl glycosides incorporating the phenol moietyRiafrecha, Leonardo EzequielVullo, DanielaOuahrani Bettache, SafiaKöhler, StephanDumy, PascalWinum, Jean YvesSupuran, Claudiu T.Colinas, Pedro AlfonsoANTIBACTERIALCARBOHYDRATECARBONIC ANHYDRASEhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A small series of C-glycosides containing the phenol moiety was tested for the inhibition of the β-class carbonic anhydrases (βCAs, EC 4.2.1.1) from Brucella suis. Many compounds showed activities in the micromolar or submicromolar range and excellent selectivity for pathogen CAs over human isozymes. Glycosides incorporating the 3-hydroxyphenyl moiety showed the best inhibition profile, and therefore this functionality represents lead for the development of novel anti-infectives with a new mechanism of action.Fil: Riafrecha, Leonardo Ezequiel. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Estudio de Compuestos Orgánicos; ArgentinaFil: Vullo, Daniela. Universita Degli Studi Di Firenze; ItaliaFil: Ouahrani Bettache, Safia. Université Montpellier; FranciaFil: Köhler, Stephan. Université Montpellier; FranciaFil: Dumy, Pascal. Ecole Nationale Supérieure de Chimie de Montpellier; FranciaFil: Winum, Jean Yves. Ecole Nationale Supérieure de Chimie de Montpellier; FranciaFil: Supuran, Claudiu T.. Universita Degli Studi Di Firenze; ItaliaFil: Colinas, Pedro Alfonso. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Estudio de Compuestos Orgánicos; ArgentinaTaylor & Francis Ltd2015-11info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/39664Riafrecha, Leonardo Ezequiel; Vullo, Daniela; Ouahrani Bettache, Safia; Köhler, Stephan; Dumy, Pascal; et al.; Inhibition of β-carbonic anhydrases from Brucella suis with C-cinnamoyl glycosides incorporating the phenol moiety; Taylor & Francis Ltd; Journal of Enzyme Inhibition and Medicinal Chemistry; 30; 6; 11-2015; 1017-10201475-6366CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.3109/14756366.2014.986120info:eu-repo/semantics/altIdentifier/url/https://www.tandfonline.com/doi/full/10.3109/14756366.2014.986120info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:33:43Zoai:ri.conicet.gov.ar:11336/39664instacron: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 10:33:43.299CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Inhibition of β-carbonic anhydrases from Brucella suis with C-cinnamoyl glycosides incorporating the phenol moiety
title Inhibition of β-carbonic anhydrases from Brucella suis with C-cinnamoyl glycosides incorporating the phenol moiety
spellingShingle Inhibition of β-carbonic anhydrases from Brucella suis with C-cinnamoyl glycosides incorporating the phenol moiety
Riafrecha, Leonardo Ezequiel
ANTIBACTERIAL
CARBOHYDRATE
CARBONIC ANHYDRASE
title_short Inhibition of β-carbonic anhydrases from Brucella suis with C-cinnamoyl glycosides incorporating the phenol moiety
title_full Inhibition of β-carbonic anhydrases from Brucella suis with C-cinnamoyl glycosides incorporating the phenol moiety
title_fullStr Inhibition of β-carbonic anhydrases from Brucella suis with C-cinnamoyl glycosides incorporating the phenol moiety
title_full_unstemmed Inhibition of β-carbonic anhydrases from Brucella suis with C-cinnamoyl glycosides incorporating the phenol moiety
title_sort Inhibition of β-carbonic anhydrases from Brucella suis with C-cinnamoyl glycosides incorporating the phenol moiety
dc.creator.none.fl_str_mv Riafrecha, Leonardo Ezequiel
Vullo, Daniela
Ouahrani Bettache, Safia
Köhler, Stephan
Dumy, Pascal
Winum, Jean Yves
Supuran, Claudiu T.
Colinas, Pedro Alfonso
author Riafrecha, Leonardo Ezequiel
author_facet Riafrecha, Leonardo Ezequiel
Vullo, Daniela
Ouahrani Bettache, Safia
Köhler, Stephan
Dumy, Pascal
Winum, Jean Yves
Supuran, Claudiu T.
Colinas, Pedro Alfonso
author_role author
author2 Vullo, Daniela
Ouahrani Bettache, Safia
Köhler, Stephan
Dumy, Pascal
Winum, Jean Yves
Supuran, Claudiu T.
Colinas, Pedro Alfonso
author2_role author
author
author
author
author
author
author
dc.subject.none.fl_str_mv ANTIBACTERIAL
CARBOHYDRATE
CARBONIC ANHYDRASE
topic ANTIBACTERIAL
CARBOHYDRATE
CARBONIC ANHYDRASE
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 small series of C-glycosides containing the phenol moiety was tested for the inhibition of the β-class carbonic anhydrases (βCAs, EC 4.2.1.1) from Brucella suis. Many compounds showed activities in the micromolar or submicromolar range and excellent selectivity for pathogen CAs over human isozymes. Glycosides incorporating the 3-hydroxyphenyl moiety showed the best inhibition profile, and therefore this functionality represents lead for the development of novel anti-infectives with a new mechanism of action.
Fil: Riafrecha, Leonardo Ezequiel. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Estudio de Compuestos Orgánicos; Argentina
Fil: Vullo, Daniela. Universita Degli Studi Di Firenze; Italia
Fil: Ouahrani Bettache, Safia. Université Montpellier; Francia
Fil: Köhler, Stephan. Université Montpellier; Francia
Fil: Dumy, Pascal. Ecole Nationale Supérieure de Chimie de Montpellier; Francia
Fil: Winum, Jean Yves. Ecole Nationale Supérieure de Chimie de Montpellier; Francia
Fil: Supuran, Claudiu T.. Universita Degli Studi Di Firenze; Italia
Fil: Colinas, Pedro Alfonso. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Estudio de Compuestos Orgánicos; Argentina
description A small series of C-glycosides containing the phenol moiety was tested for the inhibition of the β-class carbonic anhydrases (βCAs, EC 4.2.1.1) from Brucella suis. Many compounds showed activities in the micromolar or submicromolar range and excellent selectivity for pathogen CAs over human isozymes. Glycosides incorporating the 3-hydroxyphenyl moiety showed the best inhibition profile, and therefore this functionality represents lead for the development of novel anti-infectives with a new mechanism of action.
publishDate 2015
dc.date.none.fl_str_mv 2015-11
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/11336/39664
Riafrecha, Leonardo Ezequiel; Vullo, Daniela; Ouahrani Bettache, Safia; Köhler, Stephan; Dumy, Pascal; et al.; Inhibition of β-carbonic anhydrases from Brucella suis with C-cinnamoyl glycosides incorporating the phenol moiety; Taylor & Francis Ltd; Journal of Enzyme Inhibition and Medicinal Chemistry; 30; 6; 11-2015; 1017-1020
1475-6366
CONICET Digital
CONICET
url http://hdl.handle.net/11336/39664
identifier_str_mv Riafrecha, Leonardo Ezequiel; Vullo, Daniela; Ouahrani Bettache, Safia; Köhler, Stephan; Dumy, Pascal; et al.; Inhibition of β-carbonic anhydrases from Brucella suis with C-cinnamoyl glycosides incorporating the phenol moiety; Taylor & Francis Ltd; Journal of Enzyme Inhibition and Medicinal Chemistry; 30; 6; 11-2015; 1017-1020
1475-6366
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.3109/14756366.2014.986120
info:eu-repo/semantics/altIdentifier/url/https://www.tandfonline.com/doi/full/10.3109/14756366.2014.986120
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Taylor & Francis Ltd
publisher.none.fl_str_mv Taylor & Francis Ltd
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
_version_ 1844614352671342592
score 13.070432

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