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Chembiochem. 2014 Jul 7;15(10):1459-64. doi: 10.1002/cbic.201402061. Epub 2014 Jun 11.

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

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1
School of Chemistry, National University of Ireland, Galway, University Road, Galway (Ireland).

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.

KEYWORDS:

E-cadherin; antiproliferation; cell adhesion; cell-migration inhibitors; photobleaching

PMID:
24919421
DOI:
10.1002/cbic.201402061
[Indexed for MEDLINE]
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