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Biomimetics 2017, 2(3), 15; doi:10.3390/biomimetics2030015

2-S-Lipoylcaffeic Acid, a Natural Product-Based Entry to Tyrosinase Inhibition via Catechol Manipulation

1
Department of Chemical Sciences, University of Naples “Federico II”, Via Cintia 4, I-80126 Naples, Italy
2
Department of Biology, University of Naples “Federico II”, Via Cintia 4, I-80126 Naples, Italy
*
Author to whom correspondence should be addressed.
Academic Editor: Ille C. Gebeshuber
Received: 24 July 2017 / Revised: 4 August 2017 / Accepted: 9 August 2017 / Published: 10 August 2017
(This article belongs to the Special Issue Bioinspired Catechol-based Systems: Chemistry and Applications)
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Abstract

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. View Full-Text
Keywords: depigmenting agents; l-DOPA; dopachrome; tyrosinase; melanin; caffeic acid; dihydrolipoic acid; lipoic acid; keratinocytes depigmenting agents; l-DOPA; dopachrome; tyrosinase; melanin; caffeic acid; dihydrolipoic acid; lipoic acid; keratinocytes
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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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.

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