N-β-Glycosyl sulfamides are selective inhibitors of the cancer associated carbonic anhydrase isoforms IX and XII

Autores
Rodríguez, Oscar Mariano; Maresca, Alfonso; Témpera, Carlos Agustín; Bravo, Rodolfo Daniel; Colinas, Pedro Alfonso; Supuran, Claudiu T.
Año de publicación
2011
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The transmembrane isoforms of carbonic anhydrase (CA IX and XII) have been shown to be linked to carcinogenesis and their inhibition to arrest primary tumor and metastases growth. In this Letter, we present a series of peracetylated and deprotected N-β-glycosyl sulfamides that were tested for the inhibition of 4 carbonic anhydrase isoforms: the cytosolic hCA I and hCA II and transmembrane tumor-associated IX and XII. Compounds 1–4 and 6–8 selectively target cancer-associated CAs (IX and XII) with KIs in the low nanomolar range.
Fil: Rodríguez, Oscar Mariano. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Estudio de Compuestos Orgánicos; Argentina
Fil: Maresca, Alfonso. Università degli Studi di Firenze; Italia
Fil: Témpera, Carlos Agustín. 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: Bravo, Rodolfo Daniel. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Estudio de Compuestos Orgánicos; Argentina
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
Fil: Supuran, Claudiu T.. Università degli Studi di Firenze; Italia
Materia
Glycosyl sulfamides
Carbonic anhydrase
Targeted therapies
Cancer
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:11336/95100
Acceder
id CONICETDig_1b31b5bac05a449f87845e4911f45507
oai_identifier_str oai:ri.conicet.gov.ar:11336/95100
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling N-β-Glycosyl sulfamides are selective inhibitors of the cancer associated carbonic anhydrase isoforms IX and XIIRodríguez, Oscar MarianoMaresca, AlfonsoTémpera, Carlos AgustínBravo, Rodolfo DanielColinas, Pedro AlfonsoSupuran, Claudiu T.Glycosyl sulfamidesCarbonic anhydraseTargeted therapiesCancerhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1https://purl.org/becyt/ford/1.6https://purl.org/becyt/ford/1https://purl.org/becyt/ford/3.1https://purl.org/becyt/ford/3The transmembrane isoforms of carbonic anhydrase (CA IX and XII) have been shown to be linked to carcinogenesis and their inhibition to arrest primary tumor and metastases growth. In this Letter, we present a series of peracetylated and deprotected N-β-glycosyl sulfamides that were tested for the inhibition of 4 carbonic anhydrase isoforms: the cytosolic hCA I and hCA II and transmembrane tumor-associated IX and XII. Compounds 1–4 and 6–8 selectively target cancer-associated CAs (IX and XII) with KIs in the low nanomolar range.Fil: Rodríguez, Oscar Mariano. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Estudio de Compuestos Orgánicos; ArgentinaFil: Maresca, Alfonso. Università degli Studi di Firenze; ItaliaFil: Témpera, Carlos Agustín. 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: Bravo, Rodolfo Daniel. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Estudio de Compuestos Orgánicos; ArgentinaFil: 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; ArgentinaFil: Supuran, Claudiu T.. Università degli Studi di Firenze; ItaliaPergamon-Elsevier Science Ltd2011-08info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/95100Rodríguez, Oscar Mariano; Maresca, Alfonso; Témpera, Carlos Agustín; Bravo, Rodolfo Daniel; Colinas, Pedro Alfonso; et al.; N-β-Glycosyl sulfamides are selective inhibitors of the cancer associated carbonic anhydrase isoforms IX and XII; Pergamon-Elsevier Science Ltd; Biorganic and Medicinal Chemistry Letters; 21; 15; 8-2011; 4447-44500960-894XCONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0960894X11008146info:eu-repo/semantics/altIdentifier/doi/10.1016/j.bmcl.2011.06.031info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:02:39Zoai:ri.conicet.gov.ar:11336/95100instacron: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 10:02:39.383CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv N-β-Glycosyl sulfamides are selective inhibitors of the cancer associated carbonic anhydrase isoforms IX and XII
title N-β-Glycosyl sulfamides are selective inhibitors of the cancer associated carbonic anhydrase isoforms IX and XII
spellingShingle N-β-Glycosyl sulfamides are selective inhibitors of the cancer associated carbonic anhydrase isoforms IX and XII
Rodríguez, Oscar Mariano
Glycosyl sulfamides
Carbonic anhydrase
Targeted therapies
Cancer
title_short N-β-Glycosyl sulfamides are selective inhibitors of the cancer associated carbonic anhydrase isoforms IX and XII
title_full N-β-Glycosyl sulfamides are selective inhibitors of the cancer associated carbonic anhydrase isoforms IX and XII
title_fullStr N-β-Glycosyl sulfamides are selective inhibitors of the cancer associated carbonic anhydrase isoforms IX and XII
title_full_unstemmed N-β-Glycosyl sulfamides are selective inhibitors of the cancer associated carbonic anhydrase isoforms IX and XII
title_sort N-β-Glycosyl sulfamides are selective inhibitors of the cancer associated carbonic anhydrase isoforms IX and XII
dc.creator.none.fl_str_mv Rodríguez, Oscar Mariano
Maresca, Alfonso
Témpera, Carlos Agustín
Bravo, Rodolfo Daniel
Colinas, Pedro Alfonso
Supuran, Claudiu T.
author Rodríguez, Oscar Mariano
author_facet Rodríguez, Oscar Mariano
Maresca, Alfonso
Témpera, Carlos Agustín
Bravo, Rodolfo Daniel
Colinas, Pedro Alfonso
Supuran, Claudiu T.
author_role author
author2 Maresca, Alfonso
Témpera, Carlos Agustín
Bravo, Rodolfo Daniel
Colinas, Pedro Alfonso
Supuran, Claudiu T.
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv Glycosyl sulfamides
Carbonic anhydrase
Targeted therapies
Cancer
topic Glycosyl sulfamides
Carbonic anhydrase
Targeted therapies
Cancer
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
https://purl.org/becyt/ford/1.6
https://purl.org/becyt/ford/1
https://purl.org/becyt/ford/3.1
https://purl.org/becyt/ford/3
dc.description.none.fl_txt_mv The transmembrane isoforms of carbonic anhydrase (CA IX and XII) have been shown to be linked to carcinogenesis and their inhibition to arrest primary tumor and metastases growth. In this Letter, we present a series of peracetylated and deprotected N-β-glycosyl sulfamides that were tested for the inhibition of 4 carbonic anhydrase isoforms: the cytosolic hCA I and hCA II and transmembrane tumor-associated IX and XII. Compounds 1–4 and 6–8 selectively target cancer-associated CAs (IX and XII) with KIs in the low nanomolar range.
Fil: Rodríguez, Oscar Mariano. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Estudio de Compuestos Orgánicos; Argentina
Fil: Maresca, Alfonso. Università degli Studi di Firenze; Italia
Fil: Témpera, Carlos Agustín. 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: Bravo, Rodolfo Daniel. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Estudio de Compuestos Orgánicos; Argentina
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
Fil: Supuran, Claudiu T.. Università degli Studi di Firenze; Italia
description The transmembrane isoforms of carbonic anhydrase (CA IX and XII) have been shown to be linked to carcinogenesis and their inhibition to arrest primary tumor and metastases growth. In this Letter, we present a series of peracetylated and deprotected N-β-glycosyl sulfamides that were tested for the inhibition of 4 carbonic anhydrase isoforms: the cytosolic hCA I and hCA II and transmembrane tumor-associated IX and XII. Compounds 1–4 and 6–8 selectively target cancer-associated CAs (IX and XII) with KIs in the low nanomolar range.
publishDate 2011
dc.date.none.fl_str_mv 2011-08
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/11336/95100
Rodríguez, Oscar Mariano; Maresca, Alfonso; Témpera, Carlos Agustín; Bravo, Rodolfo Daniel; Colinas, Pedro Alfonso; et al.; N-β-Glycosyl sulfamides are selective inhibitors of the cancer associated carbonic anhydrase isoforms IX and XII; Pergamon-Elsevier Science Ltd; Biorganic and Medicinal Chemistry Letters; 21; 15; 8-2011; 4447-4450
0960-894X
CONICET Digital
CONICET
url http://hdl.handle.net/11336/95100
identifier_str_mv Rodríguez, Oscar Mariano; Maresca, Alfonso; Témpera, Carlos Agustín; Bravo, Rodolfo Daniel; Colinas, Pedro Alfonso; et al.; N-β-Glycosyl sulfamides are selective inhibitors of the cancer associated carbonic anhydrase isoforms IX and XII; Pergamon-Elsevier Science Ltd; Biorganic and Medicinal Chemistry Letters; 21; 15; 8-2011; 4447-4450
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/https://www.sciencedirect.com/science/article/pii/S0960894X11008146
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.bmcl.2011.06.031
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
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_ 1844613833480470528
score 13.070432

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