A novel synthetic compound, (Z)-5-(3-hydroxy-4-methoxybenzylidene)-2-iminothiazolidin-4-one (MHY773) inhibits mushroom tyrosinase. Issue 5 (4th May 2018)

• Record Type: Journal Article
• 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
• Is Part Of: Bioscience, biotechnology, and biochemistry. Volume 82:Issue 5(2018)
• Page Start: 759
• Page End: 767
• Publication Date: 2018-05-04
• Subjects: Tyrosinase -- α-melanocyte-stimulating hormone(α-MSH) -- 3-isobutyl-1-methylxanthine (IBMX) -- MHY773; Biotechnology -- Periodicals; Biochemistry -- Periodicals; 660.6
• DOI: 10.1080/09168451.2018.1445518
• Languages: English
• ISSNs: 0916-8451

Abstract

Abstract: As part of continued efforts for the development of new tyrosinase inhibitors, ( Z )-5-(substituted benzylidene)-2-iminothiazolidin-4-one derivatives (1a – 1l) were rationally synthesized and evaluated for their inhibitory potential in vitro . These compounds were designed and synthesized based on the structural attributes of a β-phenyl-α, β-unsaturated carbonyl scaffold template. Among these compounds, ( Z )-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. Abstract: : Binding mode and affinity of MHY773 with tyrosinase was investigated by enzyme kinetics and docking simulations. MHY773 showed potent tyrosinase inhibitory activity.