title: Synthesis and preliminary in vitro biological evaluation of 4-[(4-hydroxyphenyl)sulfanyl]but-3-en-2-one, a 4-mercaptophenol derivative designed as a novel bifunctional antimelanoma agent.
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.
authors: Istituto di Chimica Biomolecolare del CNR, Sezione di Padova, via Marzolo 1, Padova, Italia.
authors: Paolo
authors: P
authors: Ruzza
authors: Antonio
authors: A
authors: Rosato
authors: Alberto
authors: A
authors: Nassi
authors: Maria
authors: M
authors: Rondina
authors: Matteo
authors: M
authors: Zorzin
authors: Carlo Riccardo
authors: CR
authors: Rossi
authors: Maura
authors: M
authors: Floreani
authors: Luigi
authors: L
authors: Quintieri
mesh_terms: D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000378:metabolism / Q000494:pharmacology; D005978:Glutathione / Q000378:metabolism*; D006863:Hydrogen-Ion Concentration; D008546:Melanoma, Experimental / Q000188:drug therapy*; D051379:Mice; D014442:Monophenol Monooxygenase / Q000378:metabolism*; D010084:Oxidation-Reduction; D010654:Phenylbutyrates / Q000138:chemical synthesis* / Q000494:pharmacology; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis* / Q000494:pharmacology
chemical_list: C543613:4-((4-hydroxyphenyl)sulfanyl)but-3-en-2-one; D000970:Antineoplastic Agents; D010654:Phenylbutyrates; D013438:Sulfhydryl Compounds; D014442:Monophenol Monooxygenase; D005978:Glutathione