Publication: Anilino-1,4-naphthoquinones as potent mushroom tyrosinase inhibitors: in vitro and in silico studies
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Issued Date
2024-01-01
Resource Type
ISSN
14756366
eISSN
14756374
Scopus ID
2-s2.0-85194891833
Pubmed ID
38814149
Journal Title
Journal of Enzyme Inhibition and Medicinal Chemistry
Volume
39
Issue
1
Rights Holder(s)
SCOPUS
Bibliographic Citation
Journal of Enzyme Inhibition and Medicinal Chemistry Vol.39 No.1 (2024)
Suggested Citation
Sabuakham S., Nasoontorn S., Kongtaworn N., Rungrotmongkol T., Silsirivanit A., Pingaew R., Mahalapbutr P. Anilino-1,4-naphthoquinones as potent mushroom tyrosinase inhibitors: in vitro and in silico studies. Journal of Enzyme Inhibition and Medicinal Chemistry Vol.39 No.1 (2024). doi:10.1080/14756366.2024.2357174 Retrieved from: https://hdl.handle.net/20.500.14740/20748
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Abstract
Tyrosinase, a pivotal enzyme in melanin synthesis, is a primary target for the development of depigmenting agents. In this work, in vitro and in silico techniques were employed to identify novel tyrosinase inhibitors from a set of 12 anilino-1,4-naphthoquinone derivatives. Results from the mushroom tyrosinase activity assay indicated that, among the 12 derivatives, three compounds (1, 5, and 10) demonstrated the most significant inhibitory activity against mushroom tyrosinase, surpassing the effectiveness of the kojic acid. Molecular docking revealed that all studied derivatives interacted with copper ions and amino acid residues at the enzyme active site. Molecular dynamics simulations provided insights into the stability of enzyme–inhibitor complexes, in which compounds 1, 5, and particularly 10 displayed greater stability, atomic contacts, and structural compactness than kojic acid. Drug likeness prediction further strengthens the potential of anilino-1,4-naphthoquinones as promising candidates for the development of novel tyrosinase inhibitors for the treatment of hyperpigmentation disorders.