2. Academic Validation
  3. Discovery of a new potent inhibitor of mushroom tyrosinase (Agaricus bisporus) containing 4-(4-hydroxyphenyl)piperazin-1-yl moiety

Discovery of a new potent inhibitor of mushroom tyrosinase (Agaricus bisporus) containing 4-(4-hydroxyphenyl)piperazin-1-yl moiety

  • Bioorg Med Chem. 2020 Jun 1;28(11):115497. doi: 10.1016/j.bmc.2020.115497.
Laura De Luca 1,  Maria Paola Germanò 2,  Antonella Fais 3,  Francesca Pintus 3,  Maria Rosa Buemi 2,  Serena Vittorio 2,  Salvatore Mirabile 2,  Antonio Rapisarda 2,  Rosaria Gitto 2
Affiliations

Affiliations

  • 1 Department of Chemical, Biological, Pharmaceutical, and Environmental Sciences, Polo Universitario SS. Annunziata, University of Messina, Viale Palatucci 13, I-98168 Messina, Italy. Electronic address: [email protected].
  • 2 Department of Chemical, Biological, Pharmaceutical, and Environmental Sciences, Polo Universitario SS. Annunziata, University of Messina, Viale Palatucci 13, I-98168 Messina, Italy.
  • 3 Department of Life and Environment Sciences, University of Cagliari, I-09042 Monserrato, Cagliari, Italy.
PMID: 32312487 DOI: 10.1016/j.bmc.2020.115497
Abstract

Tyrosinase (TYR, EC 1.14.18.1) plays a pivotal role in mammalian melanogenesis and enzymatic browning of plant-derived food. Therefore, Tyrosinase inhibitors (TYRIs) can be of interest in cosmetics and pharmaceutical industries as depigmentation compounds as well as anti-browning agents. Starting from 4-benzylpiperidine derivatives that showed good inhibitory properties toward Tyrosinase from Agaricus bisporus (TyM), we synthesized a new series of TYRIs named 3-(4-benzyl-1-piperidyl)-1-(4-phenylpiperazin-1-yl)propan-1-one and 2-(4-benzyl-1-piperidyl)-1-(4-phenylpiperazin-1-yl)ethanone derivatives. Among them, compound 4b proved to be the most potent inhibitor (IC50 = 3.80 µM) and it also showed a good antioxidant activity. These new data furnished additional information about the SAR for this class of TYRIs.

Keywords

Agaricus Bisporus; Docking studies; Hela cells; Phenylpiperazines; Tyrosinase inhibitors.

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