Please use this identifier to cite or link to this item:
https://hdl.handle.net/1959.11/22967
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DC Field | Value | Language |
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dc.contributor.author | Wilkinson, Brendan | en |
dc.contributor.author | Innocenti, Alessio | en |
dc.contributor.author | Vullo, Daniela | en |
dc.contributor.author | Supuran, Claudiu T | en |
dc.contributor.author | Poulsen, Sally-Ann | en |
dc.date.accessioned | 2018-05-09T14:11:00Z | - |
dc.date.issued | 2008 | - |
dc.identifier.citation | Journal of Medicinal Chemistry, 51(6), p. 1945-1953 | en |
dc.identifier.issn | 1520-4804 | en |
dc.identifier.issn | 0022-2623 | en |
dc.identifier.uri | https://hdl.handle.net/1959.11/22967 | - |
dc.description.abstract | A library of glycoconjugate benzene sulfonamides have been synthesized and investigated for their ability to inhibit the enzymatic activity of physiologically relevant human carbonic anhydrase (hCA) isozymes: hCA I, II, and tumor-associated IX. Our synthetic strategy directly links the known CA pharmacophore (ArSO2NH2) to a sugar 'tail' moiety through a rigid 1,2,3-triazole linker unit using the Cu(I)-catalyzed 1,3-dipolar cycloaddition reaction or 'click chemistry'. Many of the glycoconjugates were potent CA inhibitors and exhibited some isozyme selectivity. In particular, the methyl-D-glucuronate triazoles 6 and 14 were potent inhibitors of hCA IX (Kis 9.9 and 8.4 nM, respectively) with selectivity also favoring this isozyme. Other exceptional compounds included the deprotected B-D-ribofuranosyl triazole 15 and α-D-mannosyl triazole 17, which were potent and selective hCA II inhibitors (Ki 7.5 nM and Ki 2.3 nM, respectively). Collectively, the results confirm that modification of ring size, stereochemical configuration, and chain length in the sugar tail moiety of glycoconjugate CA inhibitors permits tunable potency and selectivity that may constitute an important avenue for the future development of efficacious and selective CA-based therapeutics. | en |
dc.language | en | en |
dc.publisher | American Chemical Society | en |
dc.relation.ispartof | Journal of Medicinal Chemistry | en |
dc.title | Inhibition of Carbonic Anhydrases with Glycosyltriazole Benzene Sulfonamides | en |
dc.type | Journal Article | en |
dc.identifier.doi | 10.1021/jm701426t | en |
dc.subject.keywords | Organic Chemical Synthesis | en |
dc.subject.keywords | Medicinal and Biomolecular Chemistry | en |
dc.subject.keywords | Biologically Active Molecules | en |
local.contributor.firstname | Brendan | en |
local.contributor.firstname | Alessio | en |
local.contributor.firstname | Daniela | en |
local.contributor.firstname | Claudiu T | en |
local.contributor.firstname | Sally-Ann | en |
local.subject.for2008 | 030401 Biologically Active Molecules | en |
local.subject.for2008 | 030503 Organic Chemical Synthesis | en |
local.subject.for2008 | 030499 Medicinal and Biomolecular Chemistry not elsewhere classified | en |
local.subject.seo2008 | 970103 Expanding Knowledge in the Chemical Sciences | en |
local.subject.seo2008 | 929999 Health not elsewhere classified | en |
local.subject.seo2008 | 970106 Expanding Knowledge in the Biological Sciences | en |
local.profile.school | School of Science and Technology | en |
local.profile.email | bwilkin7@une.edu.au | en |
local.output.category | C1 | en |
local.record.place | au | en |
local.record.institution | University of New England | en |
local.identifier.epublicationsrecord | une-20180425-100929 | en |
local.publisher.place | United States of America | en |
local.format.startpage | 1945 | en |
local.format.endpage | 1953 | en |
local.identifier.scopusid | 41149177054 | en |
local.peerreviewed | Yes | en |
local.identifier.volume | 51 | en |
local.identifier.issue | 6 | en |
local.contributor.lastname | Wilkinson | en |
local.contributor.lastname | Innocenti | en |
local.contributor.lastname | Vullo | en |
local.contributor.lastname | Supuran | en |
local.contributor.lastname | Poulsen | en |
dc.identifier.staff | une-id:bwilkin7 | en |
local.profile.orcid | 0000-0003-1866-6540 | en |
local.profile.role | author | en |
local.profile.role | author | en |
local.profile.role | author | en |
local.profile.role | author | en |
local.profile.role | author | en |
local.identifier.unepublicationid | une:23151 | en |
local.identifier.handle | https://hdl.handle.net/1959.11/22967 | en |
dc.identifier.academiclevel | Academic | en |
local.title.maintitle | Inhibition of Carbonic Anhydrases with Glycosyltriazole Benzene Sulfonamides | en |
local.output.categorydescription | C1 Refereed Article in a Scholarly Journal | en |
local.search.author | Wilkinson, Brendan | en |
local.search.author | Innocenti, Alessio | en |
local.search.author | Vullo, Daniela | en |
local.search.author | Supuran, Claudiu T | en |
local.search.author | Poulsen, Sally-Ann | en |
local.uneassociation | Unknown | en |
local.year.published | 2008 | en |
local.subject.for2020 | 340401 Biologically active molecules | en |
local.subject.for2020 | 340499 Medicinal and biomolecular chemistry not elsewhere classified | en |
local.subject.for2020 | 340503 Organic chemical synthesis | en |
local.subject.seo2020 | 280102 Expanding knowledge in the biological sciences | en |
local.subject.seo2020 | 200199 Clinical health not elsewhere classified | en |
local.subject.seo2020 | 280105 Expanding knowledge in the chemical sciences | en |
local.codeupdate.date | 2022-02-13T17:02:17.041 | en |
local.codeupdate.eperson | bwilkin7@une.edu.au | en |
local.codeupdate.finalised | true | en |
Appears in Collections: | Journal Article School of Science and Technology |
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