Influence of S-Oxidation on Cytotoxic Activity of Oxathiole-Fused Chalcones - Publication - Bridge of Knowledge

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Influence of S-Oxidation on Cytotoxic Activity of Oxathiole-Fused Chalcones

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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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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