Abstract
We report the synthesis and preliminary in vitro biological evaluations of 4-[(4-hydroxyphenyl)sulfanyl]but-3-en-2-one, a compound designed as a potential bifunctional antimelanoma agent, bearing both a tyrosinase-activatable phenolic moiety and a GSH-reactive alpha,beta-unsaturated carbonyl group. Both the E (1) and Z (2) isomers of the synthesized compound proved to be very good substrates of mushroom tyrosinase, reacted quickly with GSH at physiological pH, and showed a significant cytotoxic activity against B16F1 murine melanoma cells.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Animals
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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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Glutathione / metabolism*
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Hydrogen-Ion Concentration
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Melanoma, Experimental / drug therapy*
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Mice
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Monophenol Monooxygenase / metabolism*
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Oxidation-Reduction
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Phenylbutyrates / chemical synthesis*
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Phenylbutyrates / pharmacology
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Sulfhydryl Compounds / chemical synthesis*
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Sulfhydryl Compounds / pharmacology
Substances
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4-((4-hydroxyphenyl)sulfanyl)but-3-en-2-one
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Antineoplastic Agents
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Phenylbutyrates
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Sulfhydryl Compounds
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Monophenol Monooxygenase
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Glutathione