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dc.contributor.authorWilkinson, Brendanen_US
dc.contributor.authorBornaghi, Laurenten_US
dc.contributor.authorHouston, Todden_US
dc.contributor.authorInnocenti, Alessioen_US
dc.contributor.authorVullo, Danielaen_US
dc.contributor.authorT. Supuran, Claudiuen_US
dc.contributor.authorPoulsen, Sally-Annen_US
dc.contributor.editorPhilip S. Portogheseen_US
dc.date.accessioned2017-05-03T11:45:26Z
dc.date.available2017-05-03T11:45:26Z
dc.date.issued2007en_US
dc.date.modified2009-12-02T05:35:56Z
dc.identifier.issn00222623en_US
dc.identifier.doi10.1021/jm061320hen_AU
dc.identifier.urihttp://hdl.handle.net/10072/18264
dc.description.abstractWe report the synthesis of a series of benzene sulfonamides containing triazole-O-glycoside tails for evaluation as carbonic anhydrase (CA) inhibitors. These glycoconjugates were synthesized by the 1,3-dipolar cycloaddition reaction of 4-azidobenzenesulfonamide with O-propynyl glycosides. Compounds were assessed for their ability to inhibit the enzymatic activity of the physiologically dominant isozymes hCA I and II and the tumor-associated isozyme hCA IX (h = human). Against hCA I these compounds were either micromolar or low nanomolar inhibitors, while against hCA II and IX inhibition in the range of 6.8-53 nM and 9.7-107 nM, respectively was observed. The most potent inhibitor against hCA IX was the galactose derivative 8 (Ki = 9.7 nM), this is so far the most potent glycoconjugate inhibitor reported for the tumor-associated hCA IX. These carbohydrate-tethered sulfonamides may prove interesting lead candidates to target tumor-associated CA isozymes, wherein the CA domain is located extracellularly.en_US
dc.description.peerreviewedYesen_US
dc.description.publicationstatusYesen_AU
dc.languageEnglishen_US
dc.language.isoen_AU
dc.publisherAmerican Chemical Societyen_US
dc.publisher.placeWashington DCen_US
dc.publisher.urihttp://pubs.acs.org/journal/jmcmaren_AU
dc.relation.ispartofstudentpublicationYen_AU
dc.relation.ispartofpagefrom1651en_US
dc.relation.ispartofpageto1657en_US
dc.relation.ispartofissue7en_US
dc.relation.ispartofjournalJournal of Medicinal Chemistryen_US
dc.relation.ispartofvolume50en_US
dc.rights.retentionYen_AU
dc.subject.fieldofresearchcode250302en_US
dc.titleCarbonic anhydrase inhibitors: inhibition of isozymes I, II and IX with triazole-linked O-glycosides of benzene sulfonamidesen_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.date.issued2007
gro.hasfulltextNo Full Text


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