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dc.contributor.authorLopez, Marie
dc.contributor.authorBornaghi, Laurent F
dc.contributor.authorInnocenti, Alessio
dc.contributor.authorVullo, Daniela
dc.contributor.authorCharman, Susan A
dc.contributor.authorSupuran, Claudiu T
dc.contributor.authorPoulsen, Sally-Ann
dc.date.accessioned2017-05-03T11:45:32Z
dc.date.available2017-05-03T11:45:32Z
dc.date.issued2010
dc.identifier.issn0022-2623
dc.identifier.doi10.1021/jm901888x
dc.identifier.urihttp://hdl.handle.net/10072/32513
dc.description.abstractThe contribution of membrane-bound carbonic anhydrases (CAs) to hypoxic tumor growth and progression in cancer implicates cancer-associated CAs as a promising drug target for oncology. In this paper, we present a new class of sulfonamide-linked neoglycoconjugate that was designed to selectively target and inhibit the extracellular domains of the cancer-relevant CA isozymes. We describe the application of novel, yet straightforward, chemistry toward the synthesis of inhibitors that comprise both S-glycosyl sulfenamides and S-glycosyl sulfonamides.We also present the CA inhibition profile of our new neoglycoconjugates, more specifically a library of 30 compounds (3-32) that were designed to optimize both SAR (structure-activity relationship) and SPR (structure-property relationship) characteristics. We show that our approach produces neutral, water-soluble, and potent inhibitors (Kis in the low nanomolar range) that target cancer-associated CAs.
dc.description.peerreviewedYes
dc.description.publicationstatusYes
dc.format.extent394459 bytes
dc.format.mimetypeapplication/pdf
dc.languageEnglish
dc.language.isoeng
dc.publisherAmerican Chemical Society
dc.publisher.placeUnited States
dc.relation.ispartofstudentpublicationN
dc.relation.ispartofpagefrom2913
dc.relation.ispartofpageto2926
dc.relation.ispartofjournalJournal of Medicinal Chemistry
dc.relation.ispartofvolume53
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.titleSulfonamide linked neoglycoconjugates – a new class of inhibitors for 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.copyrightThis document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of Medicinal Chemistry, copyright 2010 American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://dx.doi.org/10.1021/jm901888x.
gro.date.issued2015-07-30T23:04:18Z
gro.hasfulltextFull Text
gro.griffith.authorPoulsen, Sally-Ann


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