Tripeptides conjugated with thiosemicarbazones: new inhibitors of tyrosinase for cosmeceutical use
AbstractThe 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 c...
| Main Authors: | , , , , , , , , |
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| Format: | Article |
| Language: | English |
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Taylor & Francis Group
2023-12-01
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| Series: | Journal of Enzyme Inhibition and Medicinal Chemistry |
| Subjects: | |
| Online Access: | https://www.tandfonline.com/doi/10.1080/14756366.2023.2193676 |
| _version_ | 1797400946551029760 |
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| author | Patrycja Ledwoń Waldemar Goldeman Katarzyna Hałdys Michał Jewgiński Greta Calamai Joanna Rossowska Anna Maria Papini Paolo Rovero Rafał Latajka |
| author_facet | Patrycja Ledwoń Waldemar Goldeman Katarzyna Hałdys Michał Jewgiński Greta Calamai Joanna Rossowska Anna Maria Papini Paolo Rovero Rafał Latajka |
| author_sort | Patrycja Ledwoń |
| collection | DOAJ |
| description | AbstractThe 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 IC50 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. |
| first_indexed | 2024-03-09T02:02:51Z |
| format | Article |
| id | doaj.art-72c5d9c7730f47889829d5a2f1611826 |
| institution | Directory Open Access Journal |
| issn | 1475-6366 1475-6374 |
| language | English |
| last_indexed | 2024-03-09T02:02:51Z |
| publishDate | 2023-12-01 |
| publisher | Taylor & Francis Group |
| record_format | Article |
| series | Journal of Enzyme Inhibition and Medicinal Chemistry |
| spelling | doaj.art-72c5d9c7730f47889829d5a2f16118262023-12-08T03:24:22ZengTaylor & Francis GroupJournal of Enzyme Inhibition and Medicinal Chemistry1475-63661475-63742023-12-0138110.1080/14756366.2023.2193676Tripeptides conjugated with thiosemicarbazones: new inhibitors of tyrosinase for cosmeceutical usePatrycja Ledwoń0Waldemar Goldeman1Katarzyna Hałdys2Michał Jewgiński3Greta Calamai4Joanna Rossowska5Anna Maria Papini6Paolo Rovero7Rafał Latajka8Department of Bioorganic Chemistry, Faculty of Chemistry, Wroclaw University of Science and Technology, Wrocław, PolandDepartment of Organic and Medicinal Chemistry, Faculty of Chemistry, Wroclaw University of Science and Technology, Wrocław, PolandDepartment of Bioorganic Chemistry, Faculty of Chemistry, Wroclaw University of Science and Technology, Wrocław, PolandDepartment of Bioorganic Chemistry, Faculty of Chemistry, Wroclaw University of Science and Technology, Wrocław, PolandInterdepartmental Research Unit of Peptide and Protein Chemistry and Biology, Department of Neurosciences, Psychology, Drug Research and Child Health Section of Pharmaceutical Sciences and Nutraceutics, University of Florence, Sesto Fiorentino, ItalyLudwik Hirszfeld Institute of Immunology and Experimental Therapy, Polish Academy of Science, Wrocław, PolandInterdepartmental Research Unit of Peptide and Protein Chemistry and Biology, Department of Chemistry “Ugo Schiff”, University of Florence, Sesto Fiorentino, ItalyInterdepartmental Research Unit of Peptide and Protein Chemistry and Biology, Department of Neurosciences, Psychology, Drug Research and Child Health Section of Pharmaceutical Sciences and Nutraceutics, University of Florence, Sesto Fiorentino, ItalyDepartment of Bioorganic Chemistry, Faculty of Chemistry, Wroclaw University of Science and Technology, Wrocław, PolandAbstractThe 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 IC50 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.https://www.tandfonline.com/doi/10.1080/14756366.2023.2193676Tyrosinasethiosemicarbazonespeptide conjugatescosmeceuticals melanogenesis |
| spellingShingle | Patrycja Ledwoń Waldemar Goldeman Katarzyna Hałdys Michał Jewgiński Greta Calamai Joanna Rossowska Anna Maria Papini Paolo Rovero Rafał Latajka Tripeptides conjugated with thiosemicarbazones: new inhibitors of tyrosinase for cosmeceutical use Journal of Enzyme Inhibition and Medicinal Chemistry Tyrosinase thiosemicarbazones peptide conjugates cosmeceuticals melanogenesis |
| title | Tripeptides conjugated with thiosemicarbazones: new inhibitors of tyrosinase for cosmeceutical use |
| title_full | Tripeptides conjugated with thiosemicarbazones: new inhibitors of tyrosinase for cosmeceutical use |
| title_fullStr | Tripeptides conjugated with thiosemicarbazones: new inhibitors of tyrosinase for cosmeceutical use |
| title_full_unstemmed | Tripeptides conjugated with thiosemicarbazones: new inhibitors of tyrosinase for cosmeceutical use |
| title_short | Tripeptides conjugated with thiosemicarbazones: new inhibitors of tyrosinase for cosmeceutical use |
| title_sort | tripeptides conjugated with thiosemicarbazones new inhibitors of tyrosinase for cosmeceutical use |
| topic | Tyrosinase thiosemicarbazones peptide conjugates cosmeceuticals melanogenesis |
| url | https://www.tandfonline.com/doi/10.1080/14756366.2023.2193676 |
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