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dc.contributor.authorLopez, Marieen_US
dc.contributor.authorPaul, Blessyen_US
dc.contributor.authorHofmann, Andreasen_US
dc.contributor.authorMorizzi, Juliaen_US
dc.contributor.authorK. Wu, Quocen_US
dc.contributor.authorA. Charman, Susanen_US
dc.contributor.authorInnocenti, Alessioen_US
dc.contributor.authorVullo, Danielaen_US
dc.contributor.authorT. Supuran, Claudiuen_US
dc.contributor.authorPoulsen, Sally-Annen_US
dc.date.accessioned2017-05-03T15:19:44Z
dc.date.available2017-05-03T15:19:44Z
dc.date.issued2009en_US
dc.date.modified2010-06-03T09:03:46Z
dc.identifier.issn00222623en_US
dc.identifier.doi10.1021/jm900914een_AU
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.en_US
dc.description.peerreviewedYesen_US
dc.description.publicationstatusYesen_AU
dc.languageEnglishen_US
dc.language.isoen_AU
dc.publisherAmerican Chemical Societyen_US
dc.publisher.placeUnited Statesen_US
dc.publisher.urihttp://pubs.acs.org/journal/jmcmaren_AU
dc.relation.ispartofstudentpublicationYen_AU
dc.relation.ispartofpagefrom6421en_US
dc.relation.ispartofpageto6432en_US
dc.relation.ispartofissue20en_US
dc.relation.ispartofjournalJournal of Medicinal Chemistryen_US
dc.relation.ispartofvolume52en_US
dc.rights.retentionYen_AU
dc.subject.fieldofresearchStructural Chemistry and Spectroscopyen_US
dc.subject.fieldofresearchcode030606en_US
dc.titleS-glycosyl primary sulfonamides-A new structural class for selective inhibition of cancer-associated carbonic anhydrasesen_US
dc.typeJournal articleen_US
dc.type.descriptionC1 - Peer Reviewed (HERDC)en_US
dc.type.codeC - Journal Articlesen_US
gro.facultyGriffith Sciences, School of Natural Sciencesen_US
gro.rights.copyrightCopyright 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.en_AU
gro.date.issued2009
gro.hasfulltextNo Full Text


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