dc.contributor.author | Lo Re, Daniele | |
dc.contributor.author | Zhou, Ying | |
dc.contributor.author | Mucha, Joanna | |
dc.contributor.author | Jones, Leigh F. | |
dc.contributor.author | Leahy, Lorraine | |
dc.contributor.author | Santocanale, Corrado | |
dc.contributor.author | Krol, Magdalena | |
dc.contributor.author | Murphy, Paul V. | |
dc.date.accessioned | 2018-02-26T11:29:01Z | |
dc.date.available | 2018-02-26T11:29:01Z | |
dc.date.issued | 2015-11-04 | |
dc.identifier.citation | Lo Re, Daniele, Zhou, Ying, Mucha, Joanna, Jones, Leigh F., Leahy, Lorraine, Santocanale, Corrado, Krol, Magdalena, Murphy, Paul V. (2015). Synthesis of Migrastatin Analogues as Inhibitors of Tumour Cell Migration: Exploring Structural Change in and on the Macrocyclic Ring. Chemistry – A European Journal, 21(50), 18109-18121. doi: 10.1002/chem.201502861 | en_IE |
dc.identifier.issn | 1521-3765 | |
dc.identifier.uri | http://hdl.handle.net/10379/7171 | |
dc.description.abstract | Migrastatin 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-methylmigras-tatin 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.sponsorship | This publication has emanated from research supported in part by a research grant from Science Foundation Ireland (SFI) and is co-funded under the European Regional Development Fund under Grant Number 14/SP/2710. The research leading to these results has also received funding in part from the People Programme (Marie Curie Actions) of the European Union′s Seventh Framework Programme FP7/2007-2013/ under REA grant agreement No. PIEF-GA-2011-299042 and the Poland National Science Council. We acknowledge networking support and a short term scientific mission funded by the COST Action CM1106. We thank Dr. A. Calon and Dr. E. Lonardo (Institute for Research in Biomedicine, IRB Barcelona) for helpful discussion. | en_IE |
dc.format | application/pdf | en_IE |
dc.language.iso | en | en_IE |
dc.publisher | Wiley | en_IE |
dc.relation.ispartof | Chemistry-A European Journal | en |
dc.rights | Attribution-NonCommercial-NoDerivs 3.0 Ireland | |
dc.rights.uri | https://creativecommons.org/licenses/by-nc-nd/3.0/ie/ | |
dc.subject | Anomerization | en_IE |
dc.subject | Glycosidation | en_IE |
dc.subject | Natural products | en_IE |
dc.subject | Stereoselective synthesis | en_IE |
dc.subject | Tumour cell migration | en_IE |
dc.subject | WADSWORTH-EMMONS REACTION | en_IE |
dc.subject | BREAST-CANCER CELLS | en_IE |
dc.subject | MACROLIDE CORE | en_IE |
dc.subject | IN-VIVO | en_IE |
dc.subject | ETHYL (DIARYLPHOSPHONO)ACETATES | en_IE |
dc.subject | CHEMICAL-SYNTHESIS | en_IE |
dc.subject | POTENT INHIBITORS | en_IE |
dc.subject | ISO-MIGRASTATIN | en_IE |
dc.subject | GENE-EXPRESSION | en_IE |
dc.subject | FASCIN | en_IE |
dc.title | Synthesis of migrastatin analogues as inhibitors of tumour cell migration: Exploring structural change in and on the macrocyclic ring | en_IE |
dc.type | Article | en_IE |
dc.date.updated | 2016-08-09T12:43:44Z | |
dc.identifier.doi | 10.1002/chem.201502861 | |
dc.local.publishedsource | http://dx.doi.org/10.1002/chem.201502861 | en_IE |
dc.description.peer-reviewed | peer-reviewed | |
dc.contributor.funder | Science Foundation Ireland | |
dc.internal.rssid | 10467149 | |
dc.local.contact | Paul Murphy, School Of Chemistry, Room 236, Arts/Science Building, Nui Galway. 2465 Email: paul.v.murphy@nuigalway.ie | |
dc.local.copyrightchecked | No | |
dc.local.version | ACCEPTED | |
nui.item.downloads | 318 | |