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- Title
A novel synthetic compound, (<italic>Z</italic>)-5-(3-hydroxy-4-methoxybenzylidene)-2-iminothiazolidin-4-one (MHY773) inhibits mushroom tyrosinase.
- Authors
Jung, Hee Jin; Lee, Min Jung; Park, Yeo Jin; Noh, Sang Gyun; Lee, A Kyoung; Moon, Kyoung Mi; Lee, Eun Kyeong; Bang, Eun Jin; Park, Yun Jung; Kim, Su Jeong; Yang, Jungho; Ullah, Sultan; Chun, Pusoon; Jung, Young Suk; Moon, Hyung Ryong; Chung, Hae Young
- Abstract
As part of continued efforts for the development of new tyrosinase inhibitors, (<italic>Z</italic>)-5-(substituted benzylidene)-2-iminothiazolidin-4-one derivatives (1a - 1l) were rationally synthesized and evaluated for their inhibitory potential <italic>in vitro</italic>. These compounds were designed and synthesized based on the structural attributes of a β-phenyl-α,β-unsaturated carbonyl scaffold template. Among these compounds, (<italic>Z</italic>)-5-(3-hydroxy-4-methoxybenzylidene)-2-iminothiazolidin-4-one (1e, MHY773) exhibited the greatest tyrosinase inhibition (IC50 = 2.87 μM and 8.06 μM for monophenolase and diphenolase), and outperformed the positive control, kojic acid (IC50 = 15.59 and 31.61 μM). The kinetic and docking studies demonstrated that MHY773 interacted with active site of tyrosinase. Moreover, a melanin quantification assay demonstrated that MHY773 attenuates α-melanocyte-stimulating hormone (α-MSH) and 3-isobutyl-1-methylxanthine (IBMX)-induced melanin contents in B16F10 melanoma cells. Taken together, these data suggest that MHY773 suppressed the melanin production via the inhibition of tyrosinase activity. MHY773 is a promising for the development of effective pharmacological and cosmetic agents for skin-whitening.
- Subjects
MUSHROOM enzymes; PHENOL oxidase; CHEMICAL synthesis
- Publication
Bioscience, Biotechnology & Biochemistry, 2018, Vol 82, Issue 5, p759
- ISSN
0916-8451
- Publication type
Article
- DOI
10.1080/09168451.2018.1445518