Abstract:
OBJECTIVE To synthesize phthalaldehyde mono-and dithiosemicarbazones and evaluate their tyrosinase inhibitory activities and inhibition mechanisms.
METHODS Nine target compounds were synthesized through condensation reaction between thiosemicarbazide and 5 phthalaldehydes. The tyrosinase inhibitory activities and mechanisms of the target compounds were determined by measuring the rate of oxidation of
L-3-hydroxytyrosine(
L-DOPA) and enzyme inhibition kinetics experiment, respectively. The inhibition mechanisms and kinetics of selected compounds
3a and
4a were investigated.
RESULTS The structures of the target compounds were confirmed by
1H-NMR,
13C-NMR and MS. The activity test showed that all the obtained compounds displayed potent tyrosinase inhibitory activity more than kojic acid, and the phthalaldehyde dithiosemicarbazones
3a-3d showed significantly stronger activity than the corresponding monothiosemicarbazones
4a-4d. Compounds
3a and
4a were belonged to the reversible and mixed type tyrosinase inhibitors.
CONCLUSION The phthalaldehyde dithiosemicarbazones have excellent tyrosinase inhibitory activity, which deserve further study.