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dc.contributor.authorMoeker, Janina
dc.contributor.authorTeruya, Kanae
dc.contributor.authorRossit, Sabine
dc.contributor.authorWilkinson, Brendan L
dc.contributor.authorLopez, Marie
dc.contributor.authorBornaghi, Laurent F
dc.contributor.authorInnocenti, Alessio
dc.contributor.authorSupuran, Claudiu T
dc.contributor.authorPoulsen, Sally-Ann
dc.date.accessioned2017-05-03T11:45:41Z
dc.date.available2017-05-03T11:45:41Z
dc.date.issued2012
dc.date.modified2013-06-06T23:49:22Z
dc.identifier.issn0968-0896
dc.identifier.doi10.1016/j.bmc.2012.01.052
dc.identifier.urihttp://hdl.handle.net/10072/47984
dc.description.abstractA library of 32 novel glycoconjugate thiourea-bridged benzene sulfonamides have been synthesized from the reaction of glycosyl isothiocyanates with a panel of simple benzene sulfonamides comprising either a free amine or hydrazide. All compounds were investigated for their ability to inhibit the enzymatic activity of five human carbonic anhydrase (hCA) isozymes: hCA I, II and membrane-associated isozymes IX, XII and XIV. A physicochemical feature of the free sugar thioureido glycoconjugates was high water solubility (> 20 mg/mL), as well many of these compounds exhibited a desirable potency and CA isozyme selectivity profile. From this library several inhibitors displayed excellent potency-selectivity profiles for transmembrane anchored CAs over off-target CA I and II. These molecules provide potential dual-acting candidates for the development of inhibitors that target the extracellular CAs (IX, XII and XIV) - either directly as free sugars (membrane impermeable) or indirectly as acetylated prodrugs, becoming free sugars upon esterase hydrolysis.
dc.description.peerreviewedYes
dc.description.publicationstatusYes
dc.format.extent885901 bytes
dc.format.mimetypeapplication/pdf
dc.languageEnglish
dc.language.isoeng
dc.publisherElsevier
dc.publisher.placeUnited Kingdom
dc.relation.ispartofstudentpublicationN
dc.relation.ispartofpagefrom2392
dc.relation.ispartofpageto2404
dc.relation.ispartofissue7
dc.relation.ispartofjournalBioorganic & Medicinal Chemistry
dc.relation.ispartofvolume20
dc.rights.retentionY
dc.subject.fieldofresearchMedicinal and biomolecular chemistry
dc.subject.fieldofresearchBiologically active molecules
dc.subject.fieldofresearchOrganic chemistry
dc.subject.fieldofresearchPharmacology and pharmaceutical sciences
dc.subject.fieldofresearchcode3404
dc.subject.fieldofresearchcode340401
dc.subject.fieldofresearchcode3405
dc.subject.fieldofresearchcode3214
dc.titleDesign and synthesis of thiourea compounds that inhibit transmembrane anchored carbonic anhydrases
dc.typeJournal article
dc.type.descriptionC1 - Articles
dc.type.codeC - Journal Articles
gro.facultyGriffith Sciences, Griffith Institute for Drug Discovery
gro.rights.copyright© 2012 Elsevier. This is the author-manuscript version of this paper. Reproduced in accordance with the copyright policy of the publisher. Please refer to the journal's website for access to the definitive, published version.
gro.date.issued2012
gro.hasfulltextFull Text
gro.griffith.authorPoulsen, Sally-Ann


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