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Synthesis of migrastatin and its macroketone analogue and in vivo FRAP analysis of the macroketone on E-Cadherin dynamics

Lo Re, Daniele
; 
Zhou, Ying
; 
Nobis, Max
; 
Anderson, Kurt I.
; 
Murphy, Paul V.
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Identifiers
http://hdl.handle.net/10379/5768
 https://doi.org/10.13025/14915
Publication Date
2014-06-11
Keywords
E-cadherin, Antiproliferation, Cell adhesion, Cell-migration inhibitors, Photobleaching, Wadsworth-emmons reaction, Tumor metastasis, Ethyl (diarylphosphono) acetates, Molecular dynamics, Potent inhibitors, Pancreatic cancer, Macrolide core, Real time, Gene, Chemistry
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Lo Re, D,Zhou, Y,Nobis, M,Anderson, KI,Murphy, PV (2014) 'Synthesis of Migrastatin and its Macroketone Analogue and In Vivo FRAP Analysis of the Macroketone on E-Cadherin Dynamics'. Chembiochem, 15 :1459-1464.
Abstract
An efficient and scalable synthesis of a key acyclic intermediate used for the preparation of migrastatin and its macroketone analogue is described; Brown alkoxyallylation is the key step for this synthesis. The macroketone was prepared on 100 mg scale by this route. Treatment of invasive pancreatic cancer cells grown on a cell-derived matrix or as subcutaneous tumours in nude mice with the macroketone inhibited E-cadherin dynamics in a manner consistent with increased cell adhesion and reduced invasive potential.
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Wiley-VCH Verlag
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Attribution-NonCommercial-NoDerivs 3.0 Ireland
cbn
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School of Biological and Chemical Sciences (Scholarly Articles)