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Synthesis and biological evaluation of cis-restrained carbocyclic combretastatin A-4 analogs: Influence of the ring size and saturation on cytotoxic properties
C. Nowikow, R. Fuerst, M. Kauderer, C. Dank, W. Schmid, M. Hajduch, J. Rehulka, S. Gurska, O. Mokshyna, P. Polishchuk, I. Zupkó, P. Dzubak, U. Rinner,
Jazyk angličtina Země Velká Británie
Typ dokumentu časopisecké články, práce podpořená grantem
Grantová podpora
NV15-31984A
MZ0
CEP - Centrální evidence projektů
- MeSH
- kontrolní body fáze G2 buněčného cyklu účinky léků MeSH
- lidé MeSH
- modulátory tubulinu chemická syntéza metabolismus farmakologie MeSH
- molekulární struktura MeSH
- nádorové buněčné linie MeSH
- protinádorové látky chemická syntéza metabolismus farmakologie MeSH
- screeningové testy protinádorových léčiv MeSH
- simulace molekulového dockingu MeSH
- stilbeny chemická syntéza metabolismus farmakologie MeSH
- tubulin metabolismus MeSH
- vazba proteinů MeSH
- Check Tag
- lidé MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
Combretastatin A-4 (CA-4) is a highly cytotoxic natural product and several derivatives have been prepared which underwent clinical trial. These investigations revealed that the cis-stilbene moiety of the natural product is prone to undergo cis/trans isomerization under physiological conditions, reducing the overall activity of the drug candidates. Herein, we report the preparation of cis-restrained carbocyclic analogs of CA-4. The compounds, which differ by the size and hybridization of the carbocyclic ring have been evaluated for their cytotoxic properties and their ability to inhibit tubulin polymerization. Biological data, supported by molecular docking studies, identified cyclobutenyl and cyclobutyl derivatives of the natural product as highly promising drug candidates.
Department of Life Sciences University of Applied Sciences Krems Piaristengasse 1 3500 Krems Austria
Department of Pharmacodynamics and Biopharmacy University of Szeged Eötvö u 6 6720 Szeged Hungary
Institute of Organic Chemistry Graz University of Technology Stremayrgasse 9 8010 Graz Austria
Institute of Organic Chemistry University of Vienna Währinger Straße 38 1090 Vienna Austria
Citace poskytuje Crossref.org
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- $a Nowikow, Christina $u Institute of Organic Chemistry, University of Vienna, Währinger Straße 38, 1090 Vienna, Austria.
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- $a Synthesis and biological evaluation of cis-restrained carbocyclic combretastatin A-4 analogs: Influence of the ring size and saturation on cytotoxic properties / $c C. Nowikow, R. Fuerst, M. Kauderer, C. Dank, W. Schmid, M. Hajduch, J. Rehulka, S. Gurska, O. Mokshyna, P. Polishchuk, I. Zupkó, P. Dzubak, U. Rinner,
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- $a Combretastatin A-4 (CA-4) is a highly cytotoxic natural product and several derivatives have been prepared which underwent clinical trial. These investigations revealed that the cis-stilbene moiety of the natural product is prone to undergo cis/trans isomerization under physiological conditions, reducing the overall activity of the drug candidates. Herein, we report the preparation of cis-restrained carbocyclic analogs of CA-4. The compounds, which differ by the size and hybridization of the carbocyclic ring have been evaluated for their cytotoxic properties and their ability to inhibit tubulin polymerization. Biological data, supported by molecular docking studies, identified cyclobutenyl and cyclobutyl derivatives of the natural product as highly promising drug candidates.
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- $a Fuerst, Rita $u Institute of Organic Chemistry, University of Vienna, Währinger Straße 38, 1090 Vienna, Austria; Institute of Organic Chemistry, Graz University of Technology, Stremayrgasse 9, 8010 Graz, Austria.
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- $a Kauderer, Maria $u Institute of Organic Chemistry, University of Vienna, Währinger Straße 38, 1090 Vienna, Austria.
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- $a Hajduch, Marian $u Institute of Molecular and Translational Medicine, Faculty of Medicine and Dentistry, Palacky University in Olomouc, Hnevotinska 5, Olomouc, Czech Republic.
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- $a Dzubak, Petr $u Institute of Molecular and Translational Medicine, Faculty of Medicine and Dentistry, Palacky University in Olomouc, Hnevotinska 5, Olomouc, Czech Republic. Electronic address: petr.dzubak@upol.cz.
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- $a Rinner, Uwe $u Institute of Organic Chemistry, University of Vienna, Währinger Straße 38, 1090 Vienna, Austria; Department of Life Sciences, University of Applied Sciences Krems, Piaristengasse 1, 3500 Krems, Austria. Electronic address: uwe.rinner@fh-krems.ac.at.
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