Abstract
Bis-2-(2-hydroxy-phenyl)-thiazole-4-carboxamides and -thiocarboxamides (BHPTCs) form a family of gemini hexacoordinated bis-tridentate chelating scaffolds. Four molecules were synthesized and shown to chelate iron(III) efficiently with a 1:1 stoichiometry. A dithioamide BHPTC displayed promising antiproliferative activity in several cancerous cell lines, making this molecule an interesting lead compound for the design of new iron-chelating anticancer drugs. Conversely, diamide BHPTCs had significant cytoprotective activity against iron overload in HepaRG cells in vitro, and were as efficient as and less toxic than deferoxamine B (DFO).
Copyright 2009 Elsevier Ltd. All rights reserved.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Antineoplastic Agents / chemical synthesis*
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Antineoplastic Agents / chemistry
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Antineoplastic Agents / pharmacology*
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Cell Proliferation / drug effects
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Deferoxamine / pharmacology
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Dose-Response Relationship, Drug
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Drug Design
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Drug Screening Assays, Antitumor
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Humans
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Iron Chelating Agents / chemical synthesis*
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Iron Chelating Agents / chemistry
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Iron Chelating Agents / pharmacology*
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Molecular Structure
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Stereoisomerism
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Structure-Activity Relationship
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Sulfhydryl Compounds / chemistry*
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Thiazoles / chemistry*
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Tumor Cells, Cultured
Substances
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Antineoplastic Agents
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Iron Chelating Agents
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Sulfhydryl Compounds
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Thiazoles
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bis-2-(2-hydroxy-phenyl)-thiazole-4-carboxamide
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Deferoxamine