Abstract
Dimethyl-5-acetyl-4-methyl-6-(4-methylphenylimino)-6H-thiopyran-2,3-dicarboxylate (4) has been synthesized and its antiproliferative activity is reported here. Compound 4 inhibited the growth of human colon cancer cell line HCT-15 with an IC(50) value of 3.5 μM and of breast cancer cell line MCF-7 with an IC(50) value of 1.5 μM in a dose/time-dependent manner using a sulforhodamine B assay. Moreover, suppression of clonogenic activity occurred after exposure to 4 at a concentration of 4 μM for HCT-15 and 1.7 μM for MCF-7. The results also showed tumor cell invasion through matrigel and cell adhesion. The effect of ligand complexation on DNA structure led to overall affinity constant of K(4-DNA)=9.8×10(4) M(-1).
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 / metabolism
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Antineoplastic Agents / pharmacology*
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Binding, Competitive
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Breast Neoplasms / metabolism
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Breast Neoplasms / pathology
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Cell Adhesion / drug effects
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Cell Line, Tumor
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Cell Movement / drug effects
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Cell Proliferation / drug effects*
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Cell Survival / drug effects
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Collagen / metabolism
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Colonic Neoplasms / metabolism
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Colonic Neoplasms / pathology
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DNA / chemistry
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DNA / metabolism*
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Dose-Response Relationship, Drug
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Drug Combinations
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Extracellular Matrix Proteins / metabolism
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Female
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Humans
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Inhibitory Concentration 50
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Kinetics
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Laminin / metabolism
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Models, Chemical
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Molecular Structure
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Proteoglycans / metabolism
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Pyrans / chemical synthesis
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Pyrans / chemistry
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Pyrans / metabolism
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Pyrans / pharmacology*
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Sulfhydryl Compounds / chemical synthesis
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Sulfhydryl Compounds / chemistry
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Sulfhydryl Compounds / metabolism
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Sulfhydryl Compounds / pharmacology*
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Time Factors
Substances
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Antineoplastic Agents
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Drug Combinations
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Extracellular Matrix Proteins
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Laminin
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Proteoglycans
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Pyrans
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Sulfhydryl Compounds
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dimethyl-5-acetyl-4-methyl-6-(4-methylphenylimino)-6H-thiopyran-2,3-dicarboxylate
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thiopyran
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matrigel
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Collagen
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DNA