Department of Bioorganic Chemistry, Faculty of Chemistry, Wroclaw University of Science and Technology, Wrocław, Poland.
Interdepartmental 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, Italy.
J Enzyme Inhib Med Chem. 2023 Dec;38(1):2193676. doi: 10.1080/14756366.2023.2193676.
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 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. investigations explained the differences in the activity, observed among tested compounds. Mushroom tyrosinase was inhibited by TSC-conjugates at micromolar level, with IC 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.
护肤品的研发最近正在兴起。含有经证实具有功效的活性成分的化妆品配方，即药妆品，基于各种化合物，包括肽。在药妆领域已经应用了不同的具有抗酪氨酸酶活性的美白剂。尽管它们已经存在，但由于毒性、稳定性差和其他因素，其适用性往往受到限制。在这项工作中，我们研究了含硫代甲脒（TSC）-肽缀合物对二酚酶活性的抑制作用。三肽 FFY、FWY 和 FYY 通过酰胺键形成在固相与三个带有一个或两个芳环的 TSC 缀合。然后在小鼠黑素瘤 B16F0 细胞系中检查这些化合物作为酪氨酸酶和黑色素生成抑制剂的作用，随后进行这些细胞的细胞毒性测定。研究解释了在测试化合物中观察到的活性差异。蘑菇酪氨酸酶被 TSC 缀合物以微摩尔级别的水平抑制，IC 低于广泛使用的参考化合物曲酸。到目前为止，这是第一个关于与三肽缀合的硫代甲脒的报告，其合成目的是抑制酪氨酸酶。
