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Trienamine catalyzed asymmetric synthesis and biological investigation of a cytochalasin B-inspired compound collection
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...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Royal Society of Chemistry
2016
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4766597/ https://www.ncbi.nlm.nih.gov/pubmed/26606903 http://dx.doi.org/10.1039/c5ob02272j |
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author | Sellstedt, Magnus Schwalfenberg, Melanie Ziegler, Slava Antonchick, Andrey P. Waldmann, Herbert |
author_facet | Sellstedt, Magnus Schwalfenberg, Melanie Ziegler, Slava Antonchick, Andrey P. Waldmann, Herbert |
author_sort | Sellstedt, Magnus |
collection | PubMed |
description | 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. |
format | Online Article Text |
id | pubmed-4766597 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2016 |
publisher | Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-47665972016-03-08 Trienamine catalyzed asymmetric synthesis and biological investigation of a cytochalasin B-inspired compound collection Sellstedt, Magnus Schwalfenberg, Melanie Ziegler, Slava Antonchick, Andrey P. Waldmann, Herbert Org Biomol Chem Chemistry 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. Royal Society of Chemistry 2016-01-07 2015-11-26 /pmc/articles/PMC4766597/ /pubmed/26606903 http://dx.doi.org/10.1039/c5ob02272j Text en This journal is © The Royal Society of Chemistry 2015 http://creativecommons.org/licenses/by-nc/2.0/uk/ This is an Open Access article distributed under the terms of the Creative Commons Attribution Non-Commercial License (http://creativecommons.org/licenses/by-nc/2.0/uk/) which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited. |
spellingShingle | Chemistry Sellstedt, Magnus Schwalfenberg, Melanie Ziegler, Slava Antonchick, Andrey P. Waldmann, Herbert Trienamine catalyzed asymmetric synthesis and biological investigation of a cytochalasin B-inspired compound collection |
title | Trienamine catalyzed asymmetric synthesis and biological investigation of a cytochalasin B-inspired compound collection
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title_full | Trienamine catalyzed asymmetric synthesis and biological investigation of a cytochalasin B-inspired compound collection
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title_fullStr | Trienamine catalyzed asymmetric synthesis and biological investigation of a cytochalasin B-inspired compound collection
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title_full_unstemmed | Trienamine catalyzed asymmetric synthesis and biological investigation of a cytochalasin B-inspired compound collection
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title_short | Trienamine catalyzed asymmetric synthesis and biological investigation of a cytochalasin B-inspired compound collection
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title_sort | trienamine catalyzed asymmetric synthesis and biological investigation of a cytochalasin b-inspired compound collection |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4766597/ https://www.ncbi.nlm.nih.gov/pubmed/26606903 http://dx.doi.org/10.1039/c5ob02272j |
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