Discovery of a new potent inhibitor of mushroom tyrosinase (Agaricus bisporus) containing 4-(4-hydroxyphenyl)piperazin-1-yl moiety
| Autor: | Serena Vittorio, Rosaria Gitto, Antonio Rapisarda, Salvatore Mirabile, Laura De Luca, Maria Rosa Buemi, Maria Paola Germanò, Francesca Pintus, Antonella Fais |
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| Jazyk: | angličtina |
| Rok vydání: | 2020 |
| Předmět: |
Antioxidant
Cell Survival Stereochemistry medicine.medical_treatment Tyrosinase Clinical Biochemistry Agaricus Bisporus Docking studies Hela cells Phenylpiperazines Tyrosinase inhibitors Pharmaceutical Science 01 natural sciences Biochemistry Antioxidants Structure-Activity Relationship Drug Discovery medicine Browning Humans Moiety Enzyme Inhibitors Piperazine Molecular Biology Dose-Response Relationship Drug Molecular Structure Monophenol Monooxygenase 010405 organic chemistry Chemistry Organic Chemistry 0104 chemical sciences Thiazoles 010404 medicinal & biomolecular chemistry Molecular Medicine Sulfonic Acids Mushroom tyrosinase Agaricales Agaricus bisporus |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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