In this work,we studied the synthesis,cytotoxicity assay,and molecular docking of hydroxychalcone derivatives as tyrosinase inhibitors.Synthesis of chalcone derivatives was carried out through a Claisen-Schmidt conden...In this work,we studied the synthesis,cytotoxicity assay,and molecular docking of hydroxychalcone derivatives as tyrosinase inhibitors.Synthesis of chalcone derivatives was carried out through a Claisen-Schmidt condensation reaction between acetophenone and benzaldehyde derivatives under alkaline conditions for 48 h.The synthesized products were characterized by using Fourier transform infrared(FTIR),gas chromatography-mass spectrometry(GC-MS),proton and carbon nuclear magnetic resonance(1H and 13C NMR)spectrometer.The in vitro inhibitory activity was evaluated against tyrosinase enzyme by employing L-3,4-dihydroxyphenylalanine(L-DOPA)as the substrate.We successfully synthesized 4-hydroxychalcone(HC)and 4-hydroxy-3-methoxychalcone(HMC)with a yield of 60%and 76%,respectively.While the tyrosinase inhibitory test of HC and HMC gave the IC50 value of 64.35 and 21.56μg/mL,respectively,demonstrating that their inhibitory activities against tyrosinase enzyme were better compared with kojic acid and hydroquinone as the positive controls.We also found that HC gave 2025μg/m L as the IC50 value against Vero cells,confirming that it was not toxic to the normal cell line.The molecular docking study gave the root-mean-square deviation value of less than 2?.Furthermore,the binding energies of hydroxychalcone derivatives were found as-30.13 and-31.38 kJ/mol,showing that those compounds could be potentially used as the alternative tyrosinase inhibitors in medical application.展开更多
文摘In this work,we studied the synthesis,cytotoxicity assay,and molecular docking of hydroxychalcone derivatives as tyrosinase inhibitors.Synthesis of chalcone derivatives was carried out through a Claisen-Schmidt condensation reaction between acetophenone and benzaldehyde derivatives under alkaline conditions for 48 h.The synthesized products were characterized by using Fourier transform infrared(FTIR),gas chromatography-mass spectrometry(GC-MS),proton and carbon nuclear magnetic resonance(1H and 13C NMR)spectrometer.The in vitro inhibitory activity was evaluated against tyrosinase enzyme by employing L-3,4-dihydroxyphenylalanine(L-DOPA)as the substrate.We successfully synthesized 4-hydroxychalcone(HC)and 4-hydroxy-3-methoxychalcone(HMC)with a yield of 60%and 76%,respectively.While the tyrosinase inhibitory test of HC and HMC gave the IC50 value of 64.35 and 21.56μg/mL,respectively,demonstrating that their inhibitory activities against tyrosinase enzyme were better compared with kojic acid and hydroquinone as the positive controls.We also found that HC gave 2025μg/m L as the IC50 value against Vero cells,confirming that it was not toxic to the normal cell line.The molecular docking study gave the root-mean-square deviation value of less than 2?.Furthermore,the binding energies of hydroxychalcone derivatives were found as-30.13 and-31.38 kJ/mol,showing that those compounds could be potentially used as the alternative tyrosinase inhibitors in medical application.
