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Synthesis of Migrastatin and its Macroketone Analogue and In Vivo FRAP Analysis of the Macroketone on E‐Cadherin Dynamics
Author(s) -
Lo Re Daniele,
Zhou Ying,
Nobis Max,
Anderson Kurt I.,
Murphy Paul V.
Publication year - 2014
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.201402061
Subject(s) - cadherin , in vivo , chemistry , pancreatic cancer , cell , cancer research , biology , biochemistry , cancer , genetics
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.