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dc.contributor.authorLopez, Marie
dc.contributor.authorPaul, Blessy
dc.contributor.authorHofmann, Andreas
dc.contributor.authorMorizzi, Julia
dc.contributor.authorWu, Quoc K
dc.contributor.authorCharman, Susan A
dc.contributor.authorInnocenti, Alessio
dc.contributor.authorVullo, Daniela
dc.contributor.authorSupuran, Claudiu T
dc.contributor.authorPoulsen, Sally-Ann
dc.date.accessioned2017-05-03T15:19:44Z
dc.date.available2017-05-03T15:19:44Z
dc.date.issued2009
dc.date.modified2010-06-03T09:03:46Z
dc.identifier.issn0022-2623
dc.identifier.doi10.1021/jm900914e
dc.identifier.urihttp://hdl.handle.net/10072/28013
dc.description.abstractIn this paper, we present a new class of carbonic anhydrase (CA) inhibitor that was designed to selectively target the extracellular domains of the cancer-relevant CA isozymes. The aromatic moiety of the classical zinc binding sulfonamide CA inhibitors is absent from these compounds and instead they incorporate a hydrophilic mono- or disaccharide fragment directly attached to the sulfonamide group to give S-glycosyl primary sulfonamides (1-10). The inhibition properties of these compounds at the physiologically abundant human CA isozymes I and II and cancer-associated IX and XII were determined, and all compounds had moderate potency with Kis in the micromolar range. We present the crystal structures of anomeric sulfonamides 4, 7, and 10 and the sugar sulfamate drug topiramate in complex with human recombinant CA II. From these structures, we have obtained valuable insights into ligand-protein interactions of these novel carbohydrate-based sulfonamides with CA.
dc.description.peerreviewedYes
dc.description.publicationstatusYes
dc.languageEnglish
dc.language.isoeng
dc.publisherAmerican Chemical Society
dc.publisher.placeUnited States
dc.publisher.urihttp://pubs.acs.org/journal/jmcmar
dc.relation.ispartofstudentpublicationY
dc.relation.ispartofpagefrom6421
dc.relation.ispartofpageto6432
dc.relation.ispartofissue20
dc.relation.ispartofjournalJournal of Medicinal Chemistry
dc.relation.ispartofvolume52
dc.rights.retentionY
dc.subject.fieldofresearchMedicinal and biomolecular chemistry
dc.subject.fieldofresearchOrganic chemistry
dc.subject.fieldofresearchPharmacology and pharmaceutical sciences
dc.subject.fieldofresearchcode3404
dc.subject.fieldofresearchcode3405
dc.subject.fieldofresearchcode3214
dc.titleS-glycosyl primary sulfonamides-A new structural class for selective inhibition of cancer-associated carbonic anhydrases
dc.typeJournal article
dc.type.descriptionC1 - Articles
dc.type.codeC - Journal Articles
gro.facultyGriffith Sciences, School of Natural Sciences
gro.rights.copyright© 2009 American Chemical Society. Self-archiving of the author-manuscript version is not yet supported by this publisher. Please refer to the journal link for access to the definitive, published version or contact the authors for more information.
gro.date.issued2009
gro.hasfulltextNo Full Text
gro.griffith.authorPoulsen, Sally-Ann


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