Jump to main content
Jump to site search

Issue 1, 2016
Previous Article Next Article

Trienamine catalyzed asymmetric synthesis and biological investigation of a cytochalasin B-inspired compound collection

Author affiliations

Abstract

Due to their enhanced metabolic needs many cancers need a sufficient supply of glucose, and novel inhibitors of glucose import are in high demand. Cytochalasin B (CB) is a potent natural glucose import inhibitor which also impairs the actin cytoskeleton leading to undesired toxicity. With a view to identifying selective glucose import inhibitors we have developed an enantioselective trienamine catalyzed synthesis of a CB-inspired compound collection. Biological analysis revealed that indeed actin impairment can be distinguished from glucose import inhibition and led to the identification of the first selective glucose import inhibitor based on the basic structural architecture of cytochalasin B.

Graphical abstract: Trienamine catalyzed asymmetric synthesis and biological investigation of a cytochalasin B-inspired compound collection

Back to tab navigation

Supplementary files

Publication details

The article was received on 04 Nov 2015, accepted on 18 Nov 2015 and first published on 18 Nov 2015


Article type: Communication
DOI: 10.1039/C5OB02272J
Citation: Org. Biomol. Chem., 2016,14, 50-54
  • Open access: Creative Commons BY-NC license
  •   Request permissions

    Trienamine catalyzed asymmetric synthesis and biological investigation of a cytochalasin B-inspired compound collection

    M. Sellstedt, M. Schwalfenberg, S. Ziegler, A. P. Antonchick and H. Waldmann, Org. Biomol. Chem., 2016, 14, 50
    DOI: 10.1039/C5OB02272J

    This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. Material from this article can be used in other publications provided that the correct acknowledgement is given with the reproduced material and it is not used for commercial purposes.

    Reproduced material should be attributed as follows:

    • For reproduction of material from NJC:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the Centre National de la Recherche Scientifique (CNRS) and the RSC.
    • For reproduction of material from PCCP:
      [Original citation] - Published by the PCCP Owner Societies.
    • For reproduction of material from PPS:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC.
    • For reproduction of material from all other RSC journals:
      [Original citation] - Published by The Royal Society of Chemistry.

    Information about reproducing material from RSC articles with different licences is available on our Permission Requests page.

Search articles by author

Spotlight

Advertisements