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dc.contributor.authorSantocanale, Corrado
dc.contributor.authorLeahy, Lorraine
dc.contributor.authorJones, Leigh
dc.contributor.authorZhou, Ling
dc.contributor.authorMurphy, Paul V.
dc.date.accessioned2015-12-11T10:24:48Z
dc.date.available2015-12-11T10:24:48Z
dc.date.issued2015-11-04
dc.identifier.citationLo Re D, Zhou Y;Mucha J;Jones LF;Leahy L;Santocanale C;Krol M;Murphy PV (2015) 'Synthesis of migrastatin analogues as inhibitors of tumour cell migration: exploring structural change in and on the macrocyclic ring'. Chemistry (Weinheim an der Bergstrasse, Germany), .en_IE
dc.identifier.issn0947-6539
dc.identifier.urihttp://hdl.handle.net/10379/5384
dc.descriptionJournal articleen_IE
dc.description.abstractMigrastatin and isomigrastatin analogues have been synthesised in order to contribute to structure-activity studies on tumour cell migration inhibitors. These include macrocycles varying in ring size, functionality and alkene stereochemistry, as well as glucuronides. The synthesis work included application of the Saegusa-Ito reaction for regio- and stereoselective unsaturated macroketone formation, diastereoselective Brown allylation to generate 9-methylmigrastatin analogues and chelation-induced anomerisation to vary glucuronide configuration. Compounds were tested in vitro against both breast and pancreatic cancer cell lines and inhibition of tumour cell migration was observed in both wound-healing (scratch) and Boyden chamber assays. One unsaturated macroketone showed low affinity for a range of secondary drug targets, indicating it is at low risk of displaying adverse side effects..en_IE
dc.description.sponsorshipScience Foundation Ireland #14/SP/2710en_IE
dc.formatapplication/pdfen_IE
dc.language.isoenen_IE
dc.publisherWileyen_IE
dc.relation.ispartofChemistry (Weinheim an der Bergstrasse, Germany)en
dc.subjectTumour cell migrationen_IE
dc.subjectMacrocyclic ringen_IE
dc.titleSynthesis of migrastatin analogues as inhibitors of tumour cell migration: exploring structural change in and on the macrocyclic ringen_IE
dc.typeArticleen_IE
dc.date.updated2015-12-08T08:45:45Z
dc.identifier.doi10.1002/chem.201502861
dc.local.publishedsourcedx.doi.org/10.1002/chem.201502861en_IE
dc.description.peer-reviewedpeer-reviewed
dc.contributor.funder|~|
dc.internal.rssid10186086
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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