Journal
JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY
Volume 30, Issue 6, Pages 874-883Publisher
TAYLOR & FRANCIS LTD
DOI: 10.3109/14756366.2014.979346
Keywords
Antioxidant activity; kinetic studies; molecular modeling; mushroom tyrosinase inhibitors; synthesis; umbelliferone analogues
Funding
- Korea Small and Medium Business Administration
- [C0036335]
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A series of umbelliferone analogues were synthesized and their inhibitory effects on the DPPH and mushroom tyrosinase were evaluated. The results showed that some of the synthesized compounds exhibited significant mushroom tyrosinase inhibitory activities. Especially, 2-oxo-2-[(2-oxo-2H-chromen-7-yl) oxy]ethyl-2,4-dihydroxybenzoate (4e) bearing 2,4-dihydroxy substituted phenyl ring exhibited the most potent tyrosinase inhibitory activity with IC50 value 8.96 mM and IC50 value of kojic acid is 16.69. The inhibition mechanism analyzed by Lineweaver-Burk plots revealed that the type of inhibition of compound 4e on tyrosinase was noncompetitive. The docking study against tyrosinase enzyme was also performed to determine the binding affinity of the compounds. The compounds 4c and 4e showed the highest binding affinity with active binding site of tyrosinase. The initial structure activity relationships (SARs) analysis suggested that further development of such compounds might be of interest. The statistics of our results endorses that compounds 4c and 4e may serve as a structural template for the design and development of novel tyrosinase inhibitors.
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