Preprint Article Version 1 This version is not peer-reviewed

Synthesis and Structure-Activity Relationships of Resorcinol Derivatives as Highly Potent Tyrosinase Inhibitors

Version 1 : Received: 10 November 2018 / Approved: 14 November 2018 / Online: 14 November 2018 (09:59:45 CET)

How to cite: Zhou, Y.; Li, Q.; Fu, R.; Yang, H.; Mo, J.; Chen, Y.; Xia, Q. Synthesis and Structure-Activity Relationships of Resorcinol Derivatives as Highly Potent Tyrosinase Inhibitors. Preprints 2018, 2018110330 (doi: 10.20944/preprints201811.0330.v1). Zhou, Y.; Li, Q.; Fu, R.; Yang, H.; Mo, J.; Chen, Y.; Xia, Q. Synthesis and Structure-Activity Relationships of Resorcinol Derivatives as Highly Potent Tyrosinase Inhibitors. Preprints 2018, 2018110330 (doi: 10.20944/preprints201811.0330.v1).

Abstract

Compounds with tyrosinase inhibitory efficacy could be effective as depigmenting agents. Although a large number of natural and synthetic tyrosinase inhibitors have been reported, few of them are used as skin-whitening agents due to poor activity and safety concerns. 3-(2,4-Dihydroxyphenyl)propionic acid (DPPA), a naturally occurring compound isolated from Ficus carica, was previously discovered as a moderate tyrosinase inhibitor. In this study, the structure-activity relationship study of DPPA was conducted. Compound 3g, with the 2,4-resorcinol subunit and terminal hydrophobic di-butylamino group, was identified with low nanomolar enzymatic IC50 value. Additionally, compound 3g could effectively reduce melanin levels in B16-F10 melanoma cells treated with α-melanocyte-stimulating hormone (α-MSH) without affecting cell viability and proliferation. All these results indicated that compound 3g could be considered as a promising candidate for the treatment of diseases associated with hyperpigmentation.

Subject Areas

hyperpigmentation; tyrosinase inhibitors; 3-(2,4-dihydroxyphenyl)propionic acid; structure-activity relationship study; B16-F10 cellular melanogenesis inhibition

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