2-S-Lipoylcaffeic Acid, a Natural Product-Based Entry to Tyrosinase Inhibition via Catechol Manipulation
AbstractConjugation 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. View Full-Text
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Micillo, R.; Pistorio, V.; Pizzo, E.; Panzella, L.; Napolitano, A.; d’Ischia, M. 2-S-Lipoylcaffeic Acid, a Natural Product-Based Entry to Tyrosinase Inhibition via Catechol Manipulation. Biomimetics 2017, 2, 15.
Micillo R, Pistorio V, Pizzo E, Panzella L, Napolitano A, d’Ischia M. 2-S-Lipoylcaffeic Acid, a Natural Product-Based Entry to Tyrosinase Inhibition via Catechol Manipulation. Biomimetics. 2017; 2(3):15.Chicago/Turabian Style
Micillo, Raffaella; Pistorio, Valeria; Pizzo, Elio; Panzella, Lucia; Napolitano, Alessandra; d’Ischia, Marco. 2017. "2-S-Lipoylcaffeic Acid, a Natural Product-Based Entry to Tyrosinase Inhibition via Catechol Manipulation." Biomimetics 2, no. 3: 15.
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