Mostrar el registro sencillo del ítem

dc.contributor.author
Riafrecha, Leonardo Ezequiel  
dc.contributor.author
Rodríguez, Oscar Mariano  
dc.contributor.author
Vullo, Daniela  
dc.contributor.author
Supuran, Claudiu T.  
dc.contributor.author
Colinas, Pedro Alfonso  
dc.date.available
2018-01-10T17:52:08Z  
dc.date.issued
2014-08  
dc.identifier.citation
Rodríguez, Oscar Mariano; Colinas, Pedro Alfonso; Supuran, Claudiu T.; Vullo, Daniela; Riafrecha, Leonardo Ezequiel; Attachment of carbohydrates to methoxyaryl moieties leads to highly selective inhibitors of the cancer associated carbonic anhydrase isoforms IX and XII; Pergamon-Elsevier Science Ltd.; Bioorganic & Medicinal Chemistry; 22; 19; 8-2014; 5308-5314  
dc.identifier.issn
0968-0896  
dc.identifier.uri
http://hdl.handle.net/11336/32829  
dc.description.abstract
The transmembrane isoforms of carbonic anhydrase (hCA IX and XII) have been shown to be linked to carcinogenesis and their inhibition to arrest primary tumor and metastases growth. In this paper, we present a new class of C-glycosides incorporating the methoxyaryl moiety, that was designed to selectively target and inhibit the extracellular domains of the cancer-relevant CA isozymes. The glycosides have been prepared by aldol reaction of glycosyl ketones with the appropriate aromatic aldehydes. We also present the inhibition profile of our new glycomimetics, against four isozymes of carbonic anhydrase comprising hCAs I and II (cytosolic, ubiquitous isozymes) and hCAs IX and XII (tumor associated isozymes). In this study, per-O-acetylated glycoside 4, 6 and deprotected compounds 7, 9, 10 and 12 were identified as potent and highly selective inhibitors of hCA IX and XII. These results confirm that attaching carbohydrate moieties to CA methoxyaryl pharmacophore improves and enhances its inhibitory activity. These CA inhibitors have developmental potential to selectively target cancer cells, leading to cell death.  
dc.format
application/pdf  
dc.language.iso
eng  
dc.publisher
Pergamon-Elsevier Science Ltd.  
dc.rights
info:eu-repo/semantics/openAccess  
dc.rights.uri
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/  
dc.subject
Glycomimetics  
dc.subject
Enzyme Inhibitors  
dc.subject
Cancer  
dc.subject.classification
Otras Ciencias Químicas  
dc.subject.classification
Ciencias Químicas  
dc.subject.classification
CIENCIAS NATURALES Y EXACTAS  
dc.title
Attachment of carbohydrates to methoxyaryl moieties leads to highly selective inhibitors of the cancer associated carbonic anhydrase isoforms IX and XII  
dc.type
info:eu-repo/semantics/article  
dc.type
info:ar-repo/semantics/artículo  
dc.type
info:eu-repo/semantics/publishedVersion  
dc.date.updated
2018-01-10T16:52:31Z  
dc.journal.volume
22  
dc.journal.number
19  
dc.journal.pagination
5308-5314  
dc.journal.pais
Estados Unidos  
dc.journal.ciudad
New York  
dc.description.fil
Fil: Riafrecha, Leonardo Ezequiel. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química; Argentina  
dc.description.fil
Fil: Rodríguez, Oscar Mariano. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química; Argentina  
dc.description.fil
Fil: Vullo, Daniela. Universita Degli Studi Di Firenze; Italia  
dc.description.fil
Fil: Supuran, Claudiu T.. Universita Degli Studi Di Firenze; Italia  
dc.description.fil
Fil: Colinas, Pedro Alfonso. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química; Argentina  
dc.journal.title
Bioorganic & Medicinal Chemistry  
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/doi/http://dx.doi.org/10.1016/j.bmc.2014.07.052  
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0968089614005768