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A second-generation ferrocene–iminosugar hybrid with improved fucosidase binding properties

DOI: 10.1016/j.bmcl.2016.02.017 DOI Help

Authors: Audrey Hottin (Université de Reims Champagne-Ardenne) , Amandine Scandolera (Université de Reims Champagne-Ardenne) , Laurent Duca (Université de Reims Champagne-Ardenne) , Daniel Wright (University of York) , Gideon Davies (University of York) , Jean- Bernard Behr (Université de Reims Champagne-Ardenne)
Co-authored by industrial partner: No

Type: Journal Paper
Journal: Bioorganic & Medicinal Chemistry Letters , VOL 26 , PAGES 1546 - 1549

State: Published (Approved)
Published: March 2016

Open Access Open Access

Abstract: The synthesis and the biological evaluation of a new ferrocenyl-iminosugar conjugate designed for fucosidase inhibitory and anticancer activity is described. The compound showed strong affinity for fucosidase from bovine kidney (Ki = 23 nM) and from Bacteroides thetaiotaomicron (Ki = 150 nM), displaying a 10-fold tighter binding affinity for these enzymes than the previous analogs. The interaction pattern that improves binding has been evaluated through structural analysis of the inhibitor–enzyme complex. The ferrocenyl-iminosugar exhibits significant anticancer activity on MDA-MB-231 and SK-MEL28 cell lines at 100 μM.

Journal Keywords: Iminosugars; Ferrocene; Fucosidase; Inhibitors; Anticancer

Subject Areas: Chemistry, Biology and Bio-materials

Instruments: I03-Macromolecular Crystallography

Added On: 29/03/2016 10:24

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