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The cytotoxic styryl lactone goniothalamin is an inhibitor of nucleocytoplasmic transport
JournalArticle (Originalarbeit in einer wissenschaftlichen Zeitschrift)
 
ID 462454
Author(s) Wach, Jean-Yves; Güttinger, Stephan; Kutay, Ulrike; Gademann, Karl
Author(s) at UniBasel Gademann, Karl
Year 2010
Title The cytotoxic styryl lactone goniothalamin is an inhibitor of nucleocytoplasmic transport
Journal Bioorganic & medicinal chemistry letters
Volume 20
Number 9
Pages / Article-Number 2843-6
Keywords Natural products, Chemical biology, Target identification, Organic synthesis
Abstract An in vivo nuclear export assay (immunostaining of Rio2 in HeLa cells) demonstrated that (R)-goniothalamin is an inhibitor of nucleocytoplasmic transport above 500 nM, which was rationalized also by molecular modeling. The cytotoxic styryl lactone natural product was prepared via an enantioselective Cr(III) catalyzed hetero Diels-Alder reaction and a Sonogashira coupling. A series of analogs was synthesized and only the oxidized goniothalamin derivative featuring an alkyne spacer was found active. Unsaturated lactones of natural origin other than leptomycin (LMB) are thus suggested to operate via a similar mechanism targeting the CRM1 nuclear receptor. (C) 2010 Elsevier Ltd. All rights reserved.
Publisher Pergamon
ISSN/ISBN 0960-894X
edoc-URL http://edoc.unibas.ch/dok/A5841588
Full Text on edoc No
Digital Object Identifier DOI 10.1016/j.bmcl.2010.03.049
PubMed ID http://www.ncbi.nlm.nih.gov/pubmed/20381347
ISI-Number WOS:000276816600031
Document type (ISI) Journal Article
 
   

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