Development of hydroxylated naphthylchalcones as polyphenol oxidase inhibitors: Synthesis,biochemistry and molecular docking studies |
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| Institution: | 1. State Key Laboratory of Chemical Resource Engineering, Beijing University of Chemical Technology, Beijing, PR China;2. Department of Chemistry, University of Science and Technology Bannu, 28100, Khyber pakhtoonkhwa- Pakistan;3. Department of Physics, University of Peshawar, 25000, Pakistan;4. Interdisciplinary Research Centre in Biomedical Materials, COMSATS Institute of Information Technology, Lahore 54000, Pakistan |
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| Abstract: | Polyphenol oxidase (Tyrosinase) has received great attention, since it is the key enzyme in melanin biosynthesis. In this study, novel hydroxy naphthylchalcone compounds were synthesized, and their inhibitory effects on mushroom tyrosinase activity were evaluated. The structures of the compounds synthesized were confirmed by 1H NMR, 13C NMR, FTIR and HRMS. Two of the compounds synthesized inhibited the diphenolase activity of tyrosinase in a dose dependent manner and exhibited much higher tyrosinase inhibitory activities (IC50 values of 10.4 μM and 14.4 μM, respectively) than the positive control, kojic acid (IC50: 27.5 μM). Kinetic analysis showed that their inhibition was reversible. Both the novel compounds displayed competitive inhibition with their Ki values of 3.8 μM and 4.5 μM, respectively. Docking results confirmed that the active inhibitors strongly interacted with the mushroom tyrosinase residues. This study suggests hydroxy naphthylchalcone compounds to serve as promising candidates for use as depigmentation agents. |
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| Keywords: | Tyrosinase Competitive Docking Reversible |
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