Synthesis of C-cinnamoyl glycosides and their inhibitory activity against mammalian carbonic anhydrases

Autores
Riafrecha, Leonardo Ezequiel; Rodríguez, Oscar Mariano; Vullo, Daniela; Supuran, Claudiu T.; Colinas, Pedro Alfonso
Año de publicación
2012
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A small series of C-cinnamoyl glycosides incorporating the phenol moiety has been prepared by reaction of glycosyl ketones with the appropriate benzaldehydes. Glycosides were tested for the inhibition of twelve mammalian isoforms of carbonic anhydrase. This is the first study in which α-CAs have been investigated for their interaction with C-glycosides, a novel carbohydrate scaffold in the design of carbonic anhydrase inhibitors. The C-cinnamoyl glycosides were generally effective CA inhibitors, with inhibition constants in the low micromolar range against CA I, II, IV, VA, VB, VI, VII, IX, XII, XIII, XIV and ineffective inhibitors of CA III. These results confirm that attaching carbohydrate moieties to CA phenol pharmacophore improves its inhibitory activity.
Fil: Riafrecha, Leonardo Ezequiel. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Estudio de Compuestos Orgánicos; 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: Supuran, Claudiu T.. Universita Degli Studi Di Firenze; Italia
Fil: Colinas, Pedro Alfonso. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Estudio de Compuestos Orgánicos; Argentina
Materia
C-Glycosides
Carbonic Anhydrase
Phenol
Enzyme Inhibition
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:11336/22550
Acceder
id CONICETDig_77797f11fa1847b083a947292eea32b8
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network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Synthesis of C-cinnamoyl glycosides and their inhibitory activity against mammalian carbonic anhydrasesRiafrecha, Leonardo EzequielRodríguez, Oscar MarianoVullo, DanielaSupuran, Claudiu T.Colinas, Pedro AlfonsoC-GlycosidesCarbonic AnhydrasePhenolEnzyme Inhibitionhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A small series of C-cinnamoyl glycosides incorporating the phenol moiety has been prepared by reaction of glycosyl ketones with the appropriate benzaldehydes. Glycosides were tested for the inhibition of twelve mammalian isoforms of carbonic anhydrase. This is the first study in which α-CAs have been investigated for their interaction with C-glycosides, a novel carbohydrate scaffold in the design of carbonic anhydrase inhibitors. The C-cinnamoyl glycosides were generally effective CA inhibitors, with inhibition constants in the low micromolar range against CA I, II, IV, VA, VB, VI, VII, IX, XII, XIII, XIV and ineffective inhibitors of CA III. These results confirm that attaching carbohydrate moieties to CA phenol pharmacophore improves its inhibitory activity.Fil: Riafrecha, Leonardo Ezequiel. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Estudio de Compuestos Orgánicos; 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: Supuran, Claudiu T.. Universita Degli Studi Di Firenze; ItaliaFil: Colinas, Pedro Alfonso. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Estudio de Compuestos Orgánicos; ArgentinaElsevier2012-09info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/22550Riafrecha, Leonardo Ezequiel; Rodríguez, Oscar Mariano; Vullo, Daniela; Supuran, Claudiu T.; Colinas, Pedro Alfonso; Synthesis of C-cinnamoyl glycosides and their inhibitory activity against mammalian carbonic anhydrases; Elsevier; Bioorganic & Medicinal Chemistry; 21; 6; 9-2012; 1489-14940968-0896CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0968089612006992info:eu-repo/semantics/altIdentifier/doi/10.1016/j.bmc.2012.09.002info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T09:55:59Zoai:ri.conicet.gov.ar:11336/22550instacron: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 09:55:59.409CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthesis of C-cinnamoyl glycosides and their inhibitory activity against mammalian carbonic anhydrases
title Synthesis of C-cinnamoyl glycosides and their inhibitory activity against mammalian carbonic anhydrases
spellingShingle Synthesis of C-cinnamoyl glycosides and their inhibitory activity against mammalian carbonic anhydrases
Riafrecha, Leonardo Ezequiel
C-Glycosides
Carbonic Anhydrase
Phenol
Enzyme Inhibition
title_short Synthesis of C-cinnamoyl glycosides and their inhibitory activity against mammalian carbonic anhydrases
title_full Synthesis of C-cinnamoyl glycosides and their inhibitory activity against mammalian carbonic anhydrases
title_fullStr Synthesis of C-cinnamoyl glycosides and their inhibitory activity against mammalian carbonic anhydrases
title_full_unstemmed Synthesis of C-cinnamoyl glycosides and their inhibitory activity against mammalian carbonic anhydrases
title_sort Synthesis of C-cinnamoyl glycosides and their inhibitory activity against mammalian carbonic anhydrases
dc.creator.none.fl_str_mv Riafrecha, Leonardo Ezequiel
Rodríguez, Oscar Mariano
Vullo, Daniela
Supuran, Claudiu T.
Colinas, Pedro Alfonso
author Riafrecha, Leonardo Ezequiel
author_facet Riafrecha, Leonardo Ezequiel
Rodríguez, Oscar Mariano
Vullo, Daniela
Supuran, Claudiu T.
Colinas, Pedro Alfonso
author_role author
author2 Rodríguez, Oscar Mariano
Vullo, Daniela
Supuran, Claudiu T.
Colinas, Pedro Alfonso
author2_role author
author
author
author
dc.subject.none.fl_str_mv C-Glycosides
Carbonic Anhydrase
Phenol
Enzyme Inhibition
topic C-Glycosides
Carbonic Anhydrase
Phenol
Enzyme Inhibition
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 glycosides incorporating the phenol moiety has been prepared by reaction of glycosyl ketones with the appropriate benzaldehydes. Glycosides were tested for the inhibition of twelve mammalian isoforms of carbonic anhydrase. This is the first study in which α-CAs have been investigated for their interaction with C-glycosides, a novel carbohydrate scaffold in the design of carbonic anhydrase inhibitors. The C-cinnamoyl glycosides were generally effective CA inhibitors, with inhibition constants in the low micromolar range against CA I, II, IV, VA, VB, VI, VII, IX, XII, XIII, XIV and ineffective inhibitors of CA III. These results confirm that attaching carbohydrate moieties to CA phenol pharmacophore improves its inhibitory activity.
Fil: Riafrecha, Leonardo Ezequiel. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Estudio de Compuestos Orgánicos; 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: Supuran, Claudiu T.. Universita Degli Studi Di Firenze; Italia
Fil: Colinas, Pedro Alfonso. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. 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-cinnamoyl glycosides incorporating the phenol moiety has been prepared by reaction of glycosyl ketones with the appropriate benzaldehydes. Glycosides were tested for the inhibition of twelve mammalian isoforms of carbonic anhydrase. This is the first study in which α-CAs have been investigated for their interaction with C-glycosides, a novel carbohydrate scaffold in the design of carbonic anhydrase inhibitors. The C-cinnamoyl glycosides were generally effective CA inhibitors, with inhibition constants in the low micromolar range against CA I, II, IV, VA, VB, VI, VII, IX, XII, XIII, XIV and ineffective inhibitors of CA III. These results confirm that attaching carbohydrate moieties to CA phenol pharmacophore improves its inhibitory activity.
publishDate 2012
dc.date.none.fl_str_mv 2012-09
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/11336/22550
Riafrecha, Leonardo Ezequiel; Rodríguez, Oscar Mariano; Vullo, Daniela; Supuran, Claudiu T.; Colinas, Pedro Alfonso; Synthesis of C-cinnamoyl glycosides and their inhibitory activity against mammalian carbonic anhydrases; Elsevier; Bioorganic & Medicinal Chemistry; 21; 6; 9-2012; 1489-1494
0968-0896
CONICET Digital
CONICET
url http://hdl.handle.net/11336/22550
identifier_str_mv Riafrecha, Leonardo Ezequiel; Rodríguez, Oscar Mariano; Vullo, Daniela; Supuran, Claudiu T.; Colinas, Pedro Alfonso; Synthesis of C-cinnamoyl glycosides and their inhibitory activity against mammalian carbonic anhydrases; Elsevier; Bioorganic & Medicinal Chemistry; 21; 6; 9-2012; 1489-1494
0968-0896
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/S0968089612006992
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.bmc.2012.09.002
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
dc.publisher.none.fl_str_mv Elsevier
publisher.none.fl_str_mv Elsevier
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_ 1842269375680217088
score 13.13397

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