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.
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.
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.
Wiley-VCH Verlag
Publisher DOI
Attribution-NonCommercial-NoDerivs 3.0 Ireland