2-S-Lipoylcaffeic Acid, a Natural Product-Based Entry to Tyrosinase Inhibition via Catechol Manipulation
| Autor: | Raffaella Micillo, Valeria Pistorio, Elio Pizzo, Lucia Panzella, Alessandra Napolitano, Marco d’Ischia |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2017 |
| Předmět: |
depigmenting agents
dopachrome tyrosinase melanin caffeic acid dihydrolipoic acid lipoic acid keratinocytes Technology |
| Zdroj: | Biomimetics, Vol 2, Iss 3, p 15 (2017) |
| Druh dokumentu: | article |
| ISSN: | 2313-7673 |
| DOI: | 10.3390/biomimetics2030015 |
| Popis: | Conjugation of naturally occurring catecholic compounds with thiols is a versatile and facile entry to a broad range of bioinspired multifunctional compounds for diverse applications in biomedicine and materials science. We report herein the inhibition properties of the caffeic acid- dihydrolipoic acid S-conjugate, 2-S-lipoylcaffeic acid (LC), on mushroom tyrosinase. Half maximum inhibitory concentration (IC50) values of 3.22 ± 0.02 and 2.0 ± 0.1 µM were determined for the catecholase and cresolase activity of the enzyme, respectively, indicating a greater efficiency of LC compared to the parent caffeic acid and the standard inhibitor kojic acid. Analysis of the Lineweaver–Burk plot suggested a mixed-type inhibition mechanism. LC proved to be non-toxic on human keratinocytes (HaCaT) at concentrations up to 30 µM. These results would point to LC as a novel prototype of melanogenesis regulators for the treatment of pigmentary disorders. |
| Databáze: | Directory of Open Access Journals |
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