Inhibition of the β-carbonic anhydrases from Mycobacterium tuberculosis with C-cinnamoyl glycosides: Identification of the first inhibitor with anti-mycobacterial activity

Autores
Buchieri, María Virginia; Riafrecha, Leonardo Ezequiel; Rodríguez, Oscar Mariano; Vullo, Daniela; Morbidoni, Héctor Ricardo; Supuran, Claudiu T.; Colinas, Pedro Alfonso
Año de publicación
2013
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A small series of C-cinnamoyl glycoside containing the phenol moiety was tested for the inhibition of the three Mycobacterium tuberculosis b-carbonic anhydrases (CAs, EC 4.2.1.1) with activities in the low micromolar range detected. The compounds were also tested for the inhibition of growth of M. tuberculosis H37Rv strain, leading to the identification of (E)-1-(20 ,30 ,40 ,60 -tetra-O-acetyl-b-D-glucopyranosyl)-4-(3- hydroxyphenyl)but-3-en-2-one (1) as the first carbonic anhydrase inhibitor with anti-tubercular activity.
Fil: Buchieri, María Virginia. Universidad Nacional de Rosario; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Riafrecha, Leonardo Ezequiel. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Estudio de Compuestos Orgánicos; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Rodríguez, Oscar Mariano. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Estudio de Compuestos Orgánicos; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Vullo, Daniela. Universita Degli Studi Di Firenze; Italia
Fil: Morbidoni, Héctor Ricardo. Universidad Nacional de Rosario; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
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. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Materia
C-Glycosides
Mycobacterium Tuberculosis
Carbonic Anhydrase
Anti-Tubercular Activity
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/24754
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/24754
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Inhibition of the β-carbonic anhydrases from Mycobacterium tuberculosis with C-cinnamoyl glycosides: Identification of the first inhibitor with anti-mycobacterial activityBuchieri, María VirginiaRiafrecha, Leonardo EzequielRodríguez, Oscar MarianoVullo, DanielaMorbidoni, Héctor RicardoSupuran, Claudiu T.Colinas, Pedro AlfonsoC-GlycosidesMycobacterium TuberculosisCarbonic AnhydraseAnti-Tubercular Activityhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A small series of C-cinnamoyl glycoside containing the phenol moiety was tested for the inhibition of the three Mycobacterium tuberculosis b-carbonic anhydrases (CAs, EC 4.2.1.1) with activities in the low micromolar range detected. The compounds were also tested for the inhibition of growth of M. tuberculosis H37Rv strain, leading to the identification of (E)-1-(20 ,30 ,40 ,60 -tetra-O-acetyl-b-D-glucopyranosyl)-4-(3- hydroxyphenyl)but-3-en-2-one (1) as the first carbonic anhydrase inhibitor with anti-tubercular activity.Fil: Buchieri, María Virginia. Universidad Nacional de Rosario; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Riafrecha, Leonardo Ezequiel. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Estudio de Compuestos Orgánicos; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Rodríguez, Oscar Mariano. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Estudio de Compuestos Orgánicos; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Vullo, Daniela. Universita Degli Studi Di Firenze; ItaliaFil: Morbidoni, Héctor Ricardo. Universidad Nacional de Rosario; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: 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; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaPergamon-Elsevier Science Ltd.2013-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/24754Buchieri, María Virginia; Riafrecha, Leonardo Ezequiel; Rodríguez, Oscar Mariano; Vullo, Daniela; Morbidoni, Héctor Ricardo; et al.; Inhibition of the β-carbonic anhydrases from Mycobacterium tuberculosis with C-cinnamoyl glycosides: Identification of the first inhibitor with anti-mycobacterial activity; Pergamon-Elsevier Science Ltd.; Bioorganic & Medicinal Chemistry Letters; 23; 3; 1-2013; 740-7430960-894XCONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0960894X12015375info:eu-repo/semantics/altIdentifier/doi/10.1016/j.bmcl.2012.11.085info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T10:01:54Zoai:ri.conicet.gov.ar:11336/24754instacron: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:34982025-09-03 10:01:54.433CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Inhibition of the β-carbonic anhydrases from Mycobacterium tuberculosis with C-cinnamoyl glycosides: Identification of the first inhibitor with anti-mycobacterial activity
title Inhibition of the β-carbonic anhydrases from Mycobacterium tuberculosis with C-cinnamoyl glycosides: Identification of the first inhibitor with anti-mycobacterial activity
spellingShingle Inhibition of the β-carbonic anhydrases from Mycobacterium tuberculosis with C-cinnamoyl glycosides: Identification of the first inhibitor with anti-mycobacterial activity
Buchieri, María Virginia
C-Glycosides
Mycobacterium Tuberculosis
Carbonic Anhydrase
Anti-Tubercular Activity
title_short Inhibition of the β-carbonic anhydrases from Mycobacterium tuberculosis with C-cinnamoyl glycosides: Identification of the first inhibitor with anti-mycobacterial activity
title_full Inhibition of the β-carbonic anhydrases from Mycobacterium tuberculosis with C-cinnamoyl glycosides: Identification of the first inhibitor with anti-mycobacterial activity
title_fullStr Inhibition of the β-carbonic anhydrases from Mycobacterium tuberculosis with C-cinnamoyl glycosides: Identification of the first inhibitor with anti-mycobacterial activity
title_full_unstemmed Inhibition of the β-carbonic anhydrases from Mycobacterium tuberculosis with C-cinnamoyl glycosides: Identification of the first inhibitor with anti-mycobacterial activity
title_sort Inhibition of the β-carbonic anhydrases from Mycobacterium tuberculosis with C-cinnamoyl glycosides: Identification of the first inhibitor with anti-mycobacterial activity
dc.creator.none.fl_str_mv Buchieri, María Virginia
Riafrecha, Leonardo Ezequiel
Rodríguez, Oscar Mariano
Vullo, Daniela
Morbidoni, Héctor Ricardo
Supuran, Claudiu T.
Colinas, Pedro Alfonso
author Buchieri, María Virginia
author_facet Buchieri, María Virginia
Riafrecha, Leonardo Ezequiel
Rodríguez, Oscar Mariano
Vullo, Daniela
Morbidoni, Héctor Ricardo
Supuran, Claudiu T.
Colinas, Pedro Alfonso
author_role author
author2 Riafrecha, Leonardo Ezequiel
Rodríguez, Oscar Mariano
Vullo, Daniela
Morbidoni, Héctor Ricardo
Supuran, Claudiu T.
Colinas, Pedro Alfonso
author2_role author
author
author
author
author
author
dc.subject.none.fl_str_mv C-Glycosides
Mycobacterium Tuberculosis
Carbonic Anhydrase
Anti-Tubercular Activity
topic C-Glycosides
Mycobacterium Tuberculosis
Carbonic Anhydrase
Anti-Tubercular Activity
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-cinnamoyl glycoside containing the phenol moiety was tested for the inhibition of the three Mycobacterium tuberculosis b-carbonic anhydrases (CAs, EC 4.2.1.1) with activities in the low micromolar range detected. The compounds were also tested for the inhibition of growth of M. tuberculosis H37Rv strain, leading to the identification of (E)-1-(20 ,30 ,40 ,60 -tetra-O-acetyl-b-D-glucopyranosyl)-4-(3- hydroxyphenyl)but-3-en-2-one (1) as the first carbonic anhydrase inhibitor with anti-tubercular activity.
Fil: Buchieri, María Virginia. Universidad Nacional de Rosario; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Riafrecha, Leonardo Ezequiel. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Estudio de Compuestos Orgánicos; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Rodríguez, Oscar Mariano. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Estudio de Compuestos Orgánicos; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Vullo, Daniela. Universita Degli Studi Di Firenze; Italia
Fil: Morbidoni, Héctor Ricardo. Universidad Nacional de Rosario; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
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. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
description A small series of C-cinnamoyl glycoside containing the phenol moiety was tested for the inhibition of the three Mycobacterium tuberculosis b-carbonic anhydrases (CAs, EC 4.2.1.1) with activities in the low micromolar range detected. The compounds were also tested for the inhibition of growth of M. tuberculosis H37Rv strain, leading to the identification of (E)-1-(20 ,30 ,40 ,60 -tetra-O-acetyl-b-D-glucopyranosyl)-4-(3- hydroxyphenyl)but-3-en-2-one (1) as the first carbonic anhydrase inhibitor with anti-tubercular activity.
publishDate 2013
dc.date.none.fl_str_mv 2013-01
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/11336/24754
Buchieri, María Virginia; Riafrecha, Leonardo Ezequiel; Rodríguez, Oscar Mariano; Vullo, Daniela; Morbidoni, Héctor Ricardo; et al.; Inhibition of the β-carbonic anhydrases from Mycobacterium tuberculosis with C-cinnamoyl glycosides: Identification of the first inhibitor with anti-mycobacterial activity; Pergamon-Elsevier Science Ltd.; Bioorganic & Medicinal Chemistry Letters; 23; 3; 1-2013; 740-743
0960-894X
CONICET Digital
CONICET
url http://hdl.handle.net/11336/24754
identifier_str_mv Buchieri, María Virginia; Riafrecha, Leonardo Ezequiel; Rodríguez, Oscar Mariano; Vullo, Daniela; Morbidoni, Héctor Ricardo; et al.; Inhibition of the β-carbonic anhydrases from Mycobacterium tuberculosis with C-cinnamoyl glycosides: Identification of the first inhibitor with anti-mycobacterial activity; Pergamon-Elsevier Science Ltd.; Bioorganic & Medicinal Chemistry Letters; 23; 3; 1-2013; 740-743
0960-894X
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0960894X12015375
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.bmcl.2012.11.085
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
application/pdf
application/pdf
application/pdf
application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Pergamon-Elsevier Science Ltd.
publisher.none.fl_str_mv Pergamon-Elsevier Science 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_ 1842269724374728704
score 13.13397

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