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- Title
Design, Synthesis, In Vitro, and In Silico Insights of 5-(Substituted benzylidene)-2-phenylthiazol-4(5 H)-one Derivatives: A Novel Class of Anti-Melanogenic Compounds.
- Authors
Yoon, Dahye; Kang, Min Kyung; Jung, Hee Jin; Ullah, Sultan; Lee, Jieun; Jeong, Yeongmu; Noh, Sang Gyun; Kang, Dongwan; Park, Yujin; Chun, Pusoon; Chung, Hae Young; Moon, Hyung Ryong
- Abstract
(Z)-5-Benzylidene-2-phenylthiazol-4(5H)-one ((Z)-BPT) derivatives were designed by combining the structural characteristics of two tyrosinase inhibitors. The double-bond geometry of trisubstituted alkenes, (Z)-BPTs 1–14, was determined based on the 3JC,Hβ coupling constant of 1H-coupled 13C NMR spectra. Three (Z)-BPT derivatives (1–3) showed stronger tyrosinase inhibitory activities than kojic acid; in particular, 2 was to be 189-fold more potent than kojic acid. Kinetic analysis using mushroom tyrosinase indicated that 1 and 2 were competitive inhibitors, whereas 3 was a mixed-type inhibitor. The in silico results revealed that 1–3 could strongly bind to the active sites of mushroom and human tyrosinases, supporting the kinetic results. Derivatives 1 and 2 decreased the intracellular melanin contents in a concentration-dependent manner in B16F10 cells, and their anti-melanogenic efficacy exceeded that of kojic acid. The anti-tyrosinase activity of 1 and 2 in B16F10 cells was similar to their anti-melanogenic effects, suggesting that their anti-melanogenic effects were primarily owing to their anti-tyrosinase activity. Western blotting of B16F10 cells revealed that the derivatives 1 and 2 inhibited tyrosinase expression, which partially contributes to their anti-melanogenic ability. Several derivatives, including 2 and 3, exhibited potent antioxidant activities against ABTS cation radicals, DPPH radicals, ROS, and peroxynitrite. These results suggest that (Z)-BPT derivatives 1 and 2 have promising potential as novel anti-melanogenic agents.
- Subjects
PHENOL oxidase; COUPLING constants; RADICAL cations; RADICALS (Chemistry); WESTERN immunoblotting; MELANINS
- Publication
Molecules, 2023, Vol 28, Issue 8, p3293
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules28083293