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.
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.
Ruzza
Paolo
P
Istituto di Chimica Biomolecolare del CNR, Sezione di Padova, via Marzolo 1, Padova, Italia.
Rosato
Antonio
A
Nassi
Alberto
A
Rondina
Maria
M
Zorzin
Matteo
M
Rossi
Carlo Riccardo
CR
Floreani
Maura
M
Quintieri
Luigi
L
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
C543613:4-((4-hydroxyphenyl)sulfanyl)but-3-en-2-one; D000970:Antineoplastic Agents; D010654:Phenylbutyrates; D013438:Sulfhydryl Compounds; D014442:Monophenol Monooxygenase; D005978:Glutathione