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dc.contributor.authorBarron, Stephen
dc.contributor.authorMurphy, Paul V.
dc.date.accessioned2015-12-10T13:32:42Z
dc.date.available2015-12-10T13:32:42Z
dc.date.issued2014-03-20
dc.identifier.citationBarron, S,Murphy, PV (2014) 'Synthesis of iminosugar derivatives presenting naphthyl and alkyl amine interacting groups and binding to somatostatin receptors'. Medchemcomm, 5 :1150-1158.en_IE
dc.identifier.issn2040-2511
dc.identifier.urihttp://hdl.handle.net/10379/5381
dc.description.abstractThe synthesis of 1-deoxynojirimycin (DNJ) derivatives presenting a 2-naphthylmethyl and an alkyl amino side chain from L-sorbose is described. The synthetic derivatives were tested for their ability to inhibit the binding of somatostatin-14 to human recombinant somatostatin receptors (hSSTRs). One DNJ derivative showed selective binding for hSSTR5 over hSSTR4. The presence of benzyl groups and acetates on the oxygen atoms of the iminosugar scaffold led to increased affinity for both hSSTR5 and hSSTR4. Ligand-lipophilicity efficiencies (LLEs) are calculated for the iminosugar derivatives. The LLE values are significantly higher for iminosugar derivatives where hydroxyl groups are not protected, as compared to where they are benzylated. This indicates that leaving hydroxyl groups free or avoiding the use of multiple benzyl groups could be important for drug discovery research based on sugar scaffolds.en_IE
dc.description.sponsorshipMaterial presented herein was supported by Science Foundation Ireland (Grant no. 07/IN.1/B966) and the Irish Research Council through an Enterprise Partnership award part-funded by Eli Lilly (Kinsale, Ireland).
dc.formatapplication/pdfen_IE
dc.language.isoenen_IE
dc.publisherRoyal Society of Chemistryen_IE
dc.relation.ispartofMedchemcommen
dc.subjectBiological diversityen_IE
dc.subjectMedicinal chemistryen_IE
dc.subjectLibrary approachen_IE
dc.subjectDrugs discoveryen_IE
dc.subjectL-sorboseen_IE
dc.subjectScaffoldsen_IE
dc.subject1-deoxynojirimycinen_IE
dc.subjectAffinitiesen_IE
dc.subjectMoleculesen_IE
dc.subjectPyranoseen_IE
dc.subjectChemistryen_IE
dc.titleSynthesis of iminosugar derivatives presenting naphthyl and alkyl amine interacting groups and binding to somatostatin receptorsen_IE
dc.typeArticleen_IE
dc.date.updated2015-11-30T12:07:31Z
dc.identifier.doi10.1039/c4md00074a
dc.local.publishedsourcehttp://dx.doi.org/10.1039/C4MD00074Aen_IE
dc.description.peer-reviewedpeer-reviewed
dc.contributor.funder|~|
dc.internal.rssid7106177
dc.local.contactPaul Murphy, School Of Chemistry, Room 236, Arts/Science Building, Nui Galway. 2465 Email: paul.v.murphy@nuigalway.ie
dc.local.copyrightcheckedNo
dc.local.versionACCEPTED
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