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Abstract
Synthesis, in vitro cytotoxic activity, and interaction with tubulin of oxidized, isomeric 1-(5-alkoxybenzo[d] [1,3]oxathiol-6-yl)-3-phenylprop-2-en-1-ones and 1-(6- alkoxybenzo[d][1,3]oxathiol-5-yl)-3-phenylprop-2-en-1- ones are described. Most of the compounds demonstrated cytotoxic activity at submicromolar concentrations. It was found that oxidation of sulfur atom of the oxathiole-fused chalcones strongly influenced activity of the parent compounds, and that depending on relative position of the sulfur atom in the molecule, the activity was either increased or diminished. For isomers with sulfur atom para to the chalcone carbonyl group, oxidation led to increase in activity, while for isomers with sulfur atom meta to the carbonyl the activity dropped down. It was demonstrated that the compounds interact with tubulin at the colchicine binding site, and the interaction was evaluated using molecular modeling. It was concluded that the observed profound influence of oxidation of the sulfur atom on cytotoxic activity cannot be solely related to interaction of the compounds with tubulin.
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Authors (8)
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Marek T. Konieczny
- Gdański Uniwersytet Medyczny Katedra Technologii Chemicznej Leków
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Anita Bułakowska
- Gdański Uniwersytet Medyczny Katedra Chemii Organicznej
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Danuta Pirska
- Gdański Uniwersytet Medyczny Katedra Chemii Organicznej
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Wojciech Konieczny
- Gdański Uniwersytet Medyczny Katedra Chemii Organicznej
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Krzysztof Lemke
- Adamed Group Drug Discovery Department
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Details
- Category:
- Articles
- Type:
- artykuł w czasopiśmie wyróżnionym w JCR
- Published in:
-
Chemical Biology & Drug Design
no. 88,
edition 4,
pages 519 - 533,
ISSN: 1747-0277 - Language:
- English
- Publication year:
- 2016
- Bibliographic description:
- Konieczny M., Bułakowska A., Pirska D., Konieczny W., Składanowski A., Sabisz M., Wojciechowski M., Lemke k.: Influence of S-Oxidation on Cytotoxic Activity of Oxathiole-Fused Chalcones// Chemical Biology & Drug Design. -Vol. 88, iss. 4 (2016), s.519-533
- DOI:
- Digital Object Identifier (open in new tab) 10.1111/cbdd.12776
- Verified by:
- Gdańsk University of Technology
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