New Benzimidazothiazolone Derivatives As Tyrosinase Inhibitors with Potential Anti-Melanogenesis and Reactive Oxygen Species Scavenging Activities

Overview

Journal Antioxidants (Basel)

Date 2021 Aug 6

PMID 34356311

Citations 11

Authors

Hee Jin Jung

Dong Chan Choi

Sang Gyun Noh

Heejeong Choi

Inkyu Choi

Il Young Ryu

Hae Young Chung

Hyung Ryong Moon

Affiliations

Soon will be listed here.

Abstract

Thirteen ()-2-(substituted benzylidene)benzimidazothiazolone analogs were synthesized and evaluated for their inhibitory activity against mushroom tyrosinase. Among the compounds synthesized, compounds - showed greater inhibitory activity than kojic acid (IC = 18.27 ± 0.89 μM); IC = 3.70 ± 0.51 μM for ; IC = 3.05 ± 0.95 μM for ; and IC = 5.00 ± 0.38 μM for , and found to be competitive tyrosinase inhibitors. In silico molecular docking simulations demonstrated that compounds - could bind to the catalytic sites of tyrosinase. Compounds - inhibited melanin production and cellular tyrosinase activity in a concentration-dependent manner. Notably, compound dose-dependently scavenged ROS in B16F10 cells. Furthermore, compound downregulated the protein kinase A (PKA)/cAMP response element-binding protein (CREB) and mitogen-activated protein kinase (MAPK) signaling pathways, which led to a reduction in microphthalmia-associated transcription factor (MITF) expression, and decreased tyrosinase, tyrosinase related protein 1 (TRP1), and TRP2 expression, resulting in anti-melanogenesis activity. Hence, compound may serve as an anti-melanogenic agent against hyperpigmentation diseases.

Citing Articles

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