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http://dx.doi.org/10.5352/JLS.2021.31.8.719

A Novel Synthesized Tyrosinase Inhibitor, (E)-3-(4-hydroxybenzylidene) chroman-4-one (MHY1294) Inhibits α-MSH-induced Melanogenesis in B16F10 Melanoma Cells  

Jeon, Hyeyoung (College of Pharmacy, Pusan National University)
Lee, Seulah (College of Pharmacy, Pusan National University)
Yang, Seonguk (College of Pharmacy, Pusan National University)
Bang, EunJin (College of Pharmacy, Pusan National University)
Ryu, Il Young (College of Pharmacy, Pusan National University)
Park, Yujin (College of Pharmacy, Pusan National University)
Jung, Hee Jin (College of Pharmacy, Pusan National University)
Chung, Hae Young (College of Pharmacy, Pusan National University)
Moon, Hyung Ryong (College of Pharmacy, Pusan National University)
Lee, Jaewon (College of Pharmacy, Pusan National University)
Publication Information
Journal of Life Science / v.31, no.8, 2021 , pp. 719-728 More about this Journal
Abstract
Melanin pigments are abundantly distributed in mammalian skin, hair, eyes, and nervous system. Under normal physiological conditions, melanin protects the skin against various environmental stresses and acts as a physiological redox buffer to maintain homeostasis. However, abnormal melanin accumulation results in various hyperpigmentation conditions, such as chloasma, freckles, senile lentigo, and inflammatory pigmentation. Tyrosinase, a copper-containing enzyme, plays an important role in the regulation of the melanin pigment biosynthetic pathway. Although several whitening agents based on tyrosinase inhibition have been developed, their side effects, such as allergies, DNA damage, mutagenesis, and cytotoxicity of melanocytes, limit their applications. In this study, we synthesized 4-chromanone derivatives (MHY compounds) and investigated their ability to inhibit tyrosinase activity. Of these compounds, (E)-3-(4-hydroxybenzylidene)chroman-4-one (MHY1294) more potently inhibited the enzymatic activity of tyrosinase (IC50 = 5.1±0.86 μM) than kojic acid (14.3±1.43 μM), a representative tyrosinase inhibitor. In addition, MHY1294 showed competitive inhibitory action at the catalytic site of tyrosinase and had greater binding affinity at this site than kojic acid. Furthermore, MHY1294 effectively inhibited α-melanocyte stimulating hormone (α-MSH)-induced melanin synthesis and intracellular tyrosinase activity in B16F10 melanoma cells. The results of the present study indicate that MHY1294 may be considered as a candidate pharmacological agent and cosmetic whitening ingredient.
Keywords
Anti-melanogenesis; B16F10 melanoma cells; kojic acid; MHY1294; tyrosinase inhibitor;
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