Synthesis and evaluation of coumarin derivatives on antioxidative, tyrosinase inhibitory activities, melanogenesis, and in silico investigations
Document Type
Article
Publication Date
3-1-2024
Abstract
New coumarin derivatives were designed using a 2-(2-oxo-2H-chromen-4-yl)acetic acid scaffold conjugated with amino acid esters or tyramine. The anti-tyrosinase and anti-lipid peroxidation activities of the synthesized compounds were investigated. Coumarin derivatives 7,9, 11-13, 15-18 showed strong anti-lipid peroxidation activity. Compound 13 exhibited uncompetitive tyrosinase inhibitory activity with an IC50 value of 68.86 mu M. Compound 14 (% activity = 123.41) showed stronger tyrosinase activating activity than 8-methoxypsolaren (8-MOP, % activity = 109.46). In silico studies revealed different poses between the inhibitors and activators near the tyrosinase catalytic site. Compounds 13 (25-50 mu M) and 14 (25-100 mu M) did not show cytotoxicity against B16F10 cells. In contrast to the tyrosinase inhibition assay, compound 13 (50 mu M) suppressed melanogenesis in B16F10 cells with two times higher potency than KA (100 mu M). Compound 14 at 100 mu M showed melanogenesis enhancement in B16F10 cells in a dose-dependent manner, however, inferior to the 8-MOP. Based on the findings, compound 13 and 14 offer potential for development as skin-lightening agents and vitiligo therapy agents, respectively.
Keywords
Melanoma-Cells, Acid, Design
Divisions
CHEMISTRY
Funders
Prince of Songkla University
Publication Title
Scientific Reports
Volume
14
Issue
1
Publisher
Nature Research
Publisher Location
HEIDELBERGER PLATZ 3, BERLIN, 14197, GERMANY