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dc.contributor.author
Pratesi, Debora  
dc.contributor.author
Matassini, Camilla  
dc.contributor.author
Goti, Andrea  
dc.contributor.author
Angeli, Andrea  
dc.contributor.author
Carta, Fabrizio  
dc.contributor.author
Supuran, Claudiu T.  
dc.contributor.author
Spanevello, Rolando Angel  
dc.contributor.author
Cardona, Francesca  
dc.date.available
2020-11-26T14:46:10Z  
dc.date.issued
2020-05  
dc.identifier.citation
Pratesi, Debora; Matassini, Camilla; Goti, Andrea; Angeli, Andrea; Carta, Fabrizio; et al.; Glycomimetic Based Approach toward Selective Carbonic Anhydrase Inhibitors; American Chemical Society; ACS Medicinal Chemistry Letters; 11; 5; 5-2020; 727-731  
dc.identifier.issn
1948-5875  
dc.identifier.uri
http://hdl.handle.net/11336/119100  
dc.description.abstract
The synthesis of selective inhibitors of human carbonic anhydrases (hCAs) is of paramount importance to avoid side effects derived from undesired interactions with isoforms not involved in the targeted pathology, and this was partially addressed with the introduction of a sugar moiety (the so-called "sugar approach"). Since glycomimetics are considered more selective than the parent sugars in inhibiting carbohydrate-processing enzyme, we explored the possibility of further tuning the selectivity of hCAs inhibitors by combining the sulfonamide moiety with a sugar analogue residue. In particular, we report the synthesis of two novel hCAs inhibitors 2 and 3 which feature the presence of a piperidine iminosugar and an additional carbohydrate moiety derived from levoglucosenone (1), a key intermediate derived from cellulose pyrolysis. Biological assays revealed that iminosugar 2 is a very strong inhibitor of the central nervous system (CNS) abundantly expressed hCA VII (KI of 7.4 nM) and showed a remarkable selectivity profile toward this isoform. Interestingly, the presence of levoglucosenone in glycomimetic 3 imparted a strong inhibitory activity toward the tumor associated hCA IX (KI of 35.9 nM).  
dc.format
application/pdf  
dc.language.iso
eng  
dc.publisher
American Chemical Society  
dc.rights
info:eu-repo/semantics/restrictedAccess  
dc.rights.uri
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/  
dc.subject
CARBONIC ANHYDRASE INHIBITORS  
dc.subject
IMINOSUGARS  
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LEVOGLUCOSENONE  
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SULFONAMIDE  
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GLYCOMIMETIC  
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PIPERIDINE IMINOSUGAR  
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LEVOGLUCOSENONE  
dc.subject.classification
Química Orgánica  
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Ciencias Químicas  
dc.subject.classification
CIENCIAS NATURALES Y EXACTAS  
dc.title
Glycomimetic Based Approach toward Selective Carbonic Anhydrase Inhibitors  
dc.type
info:eu-repo/semantics/article  
dc.type
info:ar-repo/semantics/artículo  
dc.type
info:eu-repo/semantics/publishedVersion  
dc.date.updated
2020-08-05T16:39:37Z  
dc.identifier.eissn
1948-5875  
dc.journal.volume
11  
dc.journal.number
5  
dc.journal.pagination
727-731  
dc.journal.pais
Estados Unidos  
dc.journal.ciudad
Washington DC  
dc.description.fil
Fil: Pratesi, Debora. Università degli Studi di Firenze; Italia  
dc.description.fil
Fil: Matassini, Camilla. Università degli Studi di Firenze; Italia  
dc.description.fil
Fil: Goti, Andrea. Università degli Studi di Firenze; Italia  
dc.description.fil
Fil: Angeli, Andrea. Università degli Studi di Firenze; Italia  
dc.description.fil
Fil: Carta, Fabrizio. Università degli Studi di Firenze; Italia  
dc.description.fil
Fil: Supuran, Claudiu T.. Università degli Studi di Firenze; Italia  
dc.description.fil
Fil: Spanevello, Rolando Angel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina  
dc.description.fil
Fil: Cardona, Francesca. Università degli Studi di Firenze; Italia  
dc.journal.title
ACS Medicinal Chemistry Letters  
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/acsmedchemlett.9b00590  
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/doi/http://dx.doi.org/10.1021/acsmedchemlett.9b00590