In silico and in vitro insights into tyrosinase inhibitors with a 2-thioxooxazoline-4-one template.

ABSTRACT: The β-phenyl-α,β-unsaturated carbonyl (PUSC) scaffold confers tyrosinase inhibitory activity, and in the present study, 16 (Z)-5-(substituted benzylidene)-3-phenyl-2-thioxooxazolidin-4-one analogues containing this scaffold were synthesized. Mushroom tyrosinase inhibitory activities were examined. Compound 1c (IC₅₀ = 4.70 ± 0.40 μM) and compound 1j (IC₅₀ = 11.18 ± 0.54 μM) inhibited tyrosinase by 4.9 and 2.1-fold, respectively, and did so more potently than kojic acid (IC₅₀ = 23.18 ± 0.11 μM). Kinetic analysis of tyrosinase inhibition revealed that 1c and 1j inhibited tyrosinase competitively. Results of docking simulation with mushroom tyrosinase using four docking programs suggested that 1c and 1j bind more

SUBMITTER: Choi I 

PROVIDER: S-EPMC7753086 | biostudies-literature | 2021

REPOSITORIES: biostudies-literature