Tripeptides conjugated with thiosemicarbazones: new inhibitors of tyrosinase for cosmeceutical use

The development of skin-care products is recently growing. Cosmetic formulas containing active ingredients with proven efficacy, namely cosmeceuticals, are based on various compounds, including peptides. Different whitening agents featuring anti-tyrosinase activity have been applied in the cosmeceut...

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Bibliographic Details
Published in:Journal of enzyme inhibition and medicinal chemistry 2023-12, Vol.38 (1), p.2193676-2193676
Main Authors: Ledwoń, Patrycja, Goldeman, Waldemar, Hałdys, Katarzyna, Jewgiński, Michał, Calamai, Greta, Rossowska, Joanna, Papini, Anna Maria, Rovero, Paolo, Latajka, Rafał
Format: Article
Language:English
Subjects:
Agaricales
Amino acids
Animals
Chemistry
Chromatography
Copper
Cosmeceuticals
cosmeceuticals melanogenesis
Cytotoxicity
Enzyme Inhibitors - chemistry
Enzyme Inhibitors - pharmacology
Enzymes
Kojic acid
Melanins
Melanoma
Mice
Monophenol Monooxygenase
peptide conjugates
Peptides
Pharmaceutical sciences
Research Paper
Skin cancer
thiosemicarbazones
Thiosemicarbazones - chemistry
Thiosemicarbazones - pharmacology
Toxicity
Tyrosinase
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Summary:The development of skin-care products is recently growing. Cosmetic formulas containing active ingredients with proven efficacy, namely cosmeceuticals, are based on various compounds, including peptides. Different whitening agents featuring anti-tyrosinase activity have been applied in the cosmeceutical field. Despite their availability, their applicability is often limited due to several drawbacks including toxicity, lack of stability, and other factors. In this work, we present the inhibitory effect on diphenolase activity of thiosemicarbazone (TSC)-peptide conjugates. Tripeptides FFY, FWY, and FYY were conjugated with three TSCs bearing one or two aromatic rings via amide bond formation in a solid phase. Compounds were then examined as tyrosinase and melanogenesis inhibitors in murine melanoma B16F0 cell line, followed by the cytotoxicity assays of these cells. In silico investigations explained the differences in the activity, observed among tested compounds. Mushroom tyrosinase was inhibited by TSC1-conjugates at micromolar level, with IC 50 lower than this for kojic acid, a widely used reference compound. Up to now, this is the first report regarding thiosemicarbazones conjugated with tripeptides, synthesised for the purpose of tyrosinase inhibition.
ISSN:1475-6366
1475-6374
DOI:10.1080/14756366.2023.2193676