Abstract
A novel series of combretastatin A-4 heterocyclic analogues was prepared by replacement of the B ring with indole, benzofurane or benzothiophene, attached at the C2 position. These compounds were evaluated for their abilities to inhibit tubulin assembly: derivative cis3b, having a benzothiophene, showed an activity similar to those of colchicine or deoxypodophyllotoxine. The antiproliferative and antimitotic properties of cis3b against keratinocyte cancer cell lines were also evaluated and the intracellular organization of microtubules in the cells after treatment with both stereoisomers of 3b was also determined, using confocal microscopy.
Copyright © 2012 Elsevier Ltd. All rights reserved.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Antimitotic Agents / chemical synthesis*
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Antimitotic Agents / chemistry
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Antimitotic Agents / toxicity
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Benzofurans / chemistry
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Cell Cycle Checkpoints / drug effects
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Cell Line, Tumor
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Cell Proliferation / drug effects
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Colchicine / pharmacology
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Heterocyclic Compounds / chemistry*
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Humans
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Indoles / chemistry
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Microscopy, Confocal
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Microtubules / chemistry
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Microtubules / metabolism
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Stereoisomerism
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Stilbenes / chemical synthesis
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Stilbenes / chemistry*
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Stilbenes / toxicity
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Thiophenes / chemistry
Substances
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Antimitotic Agents
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Benzofurans
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Heterocyclic Compounds
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Indoles
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Stilbenes
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Thiophenes
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benzothiophene
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indole
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fosbretabulin
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benzofuran
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Colchicine