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Abstract
Synthesis, in vitro cytotoxic activity, and interaction with tubulin of (E)-1-(6-alkoxybenzo[d][1,3]oxathiol- 5-yl)-3-phenylprop-2-en-1-one derivatives (2) are described. Some of the compounds demonstrated cytotoxic activity at submicromolar concentrations, and the activity could be related to interaction with tubulin at the colchicine binding site. Interaction of selected derivatives with tubulinwas evaluated using molecular modeling, and two different modes of the interaction were identified. The proposed models demonstrate how particular structural fragments participate in binding to the tubulin and explain the importance of the fragments for cytotoxic activity. It was demonstrated that concerning binding to tubulin, the 6-alkoxybenzoxathiole ring can be considered as structural equivalent of trimethoxyphenyl motif of colchicine, podophyllotoxin or combretastatin A4. The observation opened new ways of rational modifications of several groups of tubulin binders.
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Authors (10)
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Marek T. Konieczny
- Medical University of Gdansk Department of Chemical Technology of Drugs
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Anita Buɬakowska
- Medical University of Gdansk Department of Organic Chemistry
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Danuta Pirska
- Medical University of Gdansk Department of Organic Chemistry
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Wojciech Konieczny
- Medical University of Gdansk Department of Organic Chemistry
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Krzysztof Lemke
- Adamed Group Drug Discovery Department
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Anna Pieczykolan
- Adamed Group Drug Discovery Department
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Details
- Category:
- Articles
- Type:
- artykuł w czasopiśmie wyróżnionym w JCR
- Published in:
-
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
no. 89,
pages 733 - 742,
ISSN: 0223-5234 - Language:
- English
- Publication year:
- 2015
- Bibliographic description:
- Konieczny M., Buɬakowska A., Pirska D., Konieczny W., Składanowski A., Sabisz M., Wojciechowski M., Lemke k., Pieczykolan A., Strożek W.: Structural factors affecting affinity of cytotoxic oxathiole-fused chalcones toward tubulin// EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY. -Vol. 89, (2015), s.733-742
- DOI:
- Digital Object Identifier (open in new tab) 10.1016/j.ejmech.2014.10.075
- Verified by:
- Gdańsk University of Technology
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