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Int. J. Mol. Sci. 2018, 19(3), 690;

Structure-Activity Relationships of Thiazolyl Resorcinols, Potent and Selective Inhibitors of Human Tyrosinase

Front End Innovation, Beiersdorf AG, 20245 Hamburg, Germany
Institute of Physiological Chemistry, Philipps University, 35032 Marburg, Germany
Author to whom correspondence should be addressed.
Received: 28 January 2018 / Revised: 13 February 2018 / Accepted: 24 February 2018 / Published: 28 February 2018
(This article belongs to the Special Issue Melanins and Melanogenesis: From Nature to Applications)
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Tyrosinase inhibitors are of great clinical interest as agents for the treatment of hyperpigmentary disorders; however, most compounds described in the literature lack clinical efficiency due to insufficient inhibitory activity against human tyrosinase (hTyr). Recently, we reported that thiazolyl resorcinols (4-resorcinylthiazol-2-amines and -amides) are both selective and efficacious inhibitors of hTyr in vitro and in vivo. Here, we measured dose-activity profiles of a large number of thiazolyl resorcinols and analogous compounds to better understand the molecular basis of their interaction with hTyr. We show that both the resorcinyl moiety and the thiazole ring must be intact to allow efficient inhibition of hTyr, while the substituents at the thiazole 2-amino group confer additional inhibitory activity, depending on their size and polarity. The results of molecular docking simulations were in excellent agreement with the experimental data, affording a rationale for the structural importance of either ring. We further propose that a special type of interaction between the thiazole sulfur and a conserved asparagine residue is partially responsible for the superior inhibitory activity of thiazolyl resorcinols against hTyr. View Full-Text
Keywords: tyrosinase; human; inhibition; thiazolyl resorcinols; structure; activity tyrosinase; human; inhibition; thiazolyl resorcinols; structure; activity

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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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Mann, T.; Scherner, C.; Röhm, K.-H.; Kolbe, L. Structure-Activity Relationships of Thiazolyl Resorcinols, Potent and Selective Inhibitors of Human Tyrosinase. Int. J. Mol. Sci. 2018, 19, 690.

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