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4-(Phenylsulfanyl)butan-2-One Suppresses Melanin Synthesis and Melanosome Maturation In Vitro and In Vivo

View Article: PubMed Central

ABSTRACT

In this study, we screened compounds with skin whitening properties and favorable safety profiles from a series of marine related natural products, which were isolated from Formosan soft coral Cladiella australis. Our results indicated that 4-(phenylsulfanyl)butan-2-one could successfully inhibit pigment generation processes in mushroom tyrosinase platform assay, probably through the suppression of tyrosinase activity to be a non-competitive inhibitor of tyrosinase. In cell-based viability examinations, it demonstrated low cytotoxicity on melanoma cells and other normal human cells. It exhibited stronger inhibitions of melanin production and tyrosinase activity than arbutin or 1-phenyl-2-thiourea (PTU). Also, we discovered that 4-(phenylsulfanyl)butan-2-one reduces the protein expressions of melanin synthesis-related proteins, including the microphthalmia-associated transcription factor (MITF), tyrosinase-related protein-1 (Trp-1), dopachrome tautomerase (DCT, Trp-2), and glycoprotein 100 (GP100). In an in vivo zebrafish model, it presented a remarkable suppression in melanogenesis after 48 h. In summary, our in vitro and in vivo biological assays showed that 4-(phenylsulfanyl)butan-2-one possesses anti-melanogenic properties that are significant in medical cosmetology.

No MeSH data available.


Tyrosinase activity and melanin content of 4-(phenylsulfanyl)butan-2-one treated B16-F10 cells. (A) Tyrosinase activities of B16-F10 cells after 24 h treatment with various concentrations of 4-(phenylsulfanyl)butan-2-one; (B) Melanin contents and the photographs on the top are from pellet collection; and (C) Cultured-cell photographs were taken for melanin accumulation in B16-F10 with various concentration of 4-(phenylsulfanyl)butan-2-one. The vehicle control group is DMSO (0.5%), and arbutin (1000 µM) and PTU (300 µM) are the positive control groups. (* p < 0.05 compared to the control group at 24 h; and # p < 0.05 compared to the control group at 48 h).
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ijms-16-20240-f003: Tyrosinase activity and melanin content of 4-(phenylsulfanyl)butan-2-one treated B16-F10 cells. (A) Tyrosinase activities of B16-F10 cells after 24 h treatment with various concentrations of 4-(phenylsulfanyl)butan-2-one; (B) Melanin contents and the photographs on the top are from pellet collection; and (C) Cultured-cell photographs were taken for melanin accumulation in B16-F10 with various concentration of 4-(phenylsulfanyl)butan-2-one. The vehicle control group is DMSO (0.5%), and arbutin (1000 µM) and PTU (300 µM) are the positive control groups. (* p < 0.05 compared to the control group at 24 h; and # p < 0.05 compared to the control group at 48 h).

Mentions: To clearly understand the inhibitory effect of 4-(phenylsulfanyl)butan-2 on melanogenesis, we assessed intracellular tyrosinase activity in B16-F10 cells. Cells were cultured in 10 and 50 µM (suitable concentrations as suggested by the cell viability assay) for two periods of time, 24 h and 48 h. After incubation, tyrosinase activities were suppressed to a greater extent than those of the vehicle control, 1,000 µM arbutin, and 300 µM PTU (Figure 3A). We studied the inhibitory effects of high concentrations of PTU and arbutin, which are renowned melanin inhibitors, on pigment generation in the examination platforms. We further determined the effectiveness of 4-(phenylsulfanyl)butan-2 on melanin production using B16-F10 cells cultured with the same aforementioned agent concentrations. The melanin assay results clearly showed that the sample reduced the melanin content of B16-F10 cells in both time- and dose-dependent manners (Figure 3B,C). 4-(Phenylsulfanyl)butan-2 significantly inhibited melanin synthesis, and produced less than 30% of baseline levels at both doses (10 and 50 µM) for 48 h compared to arbutin or PTU, respectively.


4-(Phenylsulfanyl)butan-2-One Suppresses Melanin Synthesis and Melanosome Maturation In Vitro and In Vivo
Tyrosinase activity and melanin content of 4-(phenylsulfanyl)butan-2-one treated B16-F10 cells. (A) Tyrosinase activities of B16-F10 cells after 24 h treatment with various concentrations of 4-(phenylsulfanyl)butan-2-one; (B) Melanin contents and the photographs on the top are from pellet collection; and (C) Cultured-cell photographs were taken for melanin accumulation in B16-F10 with various concentration of 4-(phenylsulfanyl)butan-2-one. The vehicle control group is DMSO (0.5%), and arbutin (1000 µM) and PTU (300 µM) are the positive control groups. (* p < 0.05 compared to the control group at 24 h; and # p < 0.05 compared to the control group at 48 h).
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ijms-16-20240-f003: Tyrosinase activity and melanin content of 4-(phenylsulfanyl)butan-2-one treated B16-F10 cells. (A) Tyrosinase activities of B16-F10 cells after 24 h treatment with various concentrations of 4-(phenylsulfanyl)butan-2-one; (B) Melanin contents and the photographs on the top are from pellet collection; and (C) Cultured-cell photographs were taken for melanin accumulation in B16-F10 with various concentration of 4-(phenylsulfanyl)butan-2-one. The vehicle control group is DMSO (0.5%), and arbutin (1000 µM) and PTU (300 µM) are the positive control groups. (* p < 0.05 compared to the control group at 24 h; and # p < 0.05 compared to the control group at 48 h).
Mentions: To clearly understand the inhibitory effect of 4-(phenylsulfanyl)butan-2 on melanogenesis, we assessed intracellular tyrosinase activity in B16-F10 cells. Cells were cultured in 10 and 50 µM (suitable concentrations as suggested by the cell viability assay) for two periods of time, 24 h and 48 h. After incubation, tyrosinase activities were suppressed to a greater extent than those of the vehicle control, 1,000 µM arbutin, and 300 µM PTU (Figure 3A). We studied the inhibitory effects of high concentrations of PTU and arbutin, which are renowned melanin inhibitors, on pigment generation in the examination platforms. We further determined the effectiveness of 4-(phenylsulfanyl)butan-2 on melanin production using B16-F10 cells cultured with the same aforementioned agent concentrations. The melanin assay results clearly showed that the sample reduced the melanin content of B16-F10 cells in both time- and dose-dependent manners (Figure 3B,C). 4-(Phenylsulfanyl)butan-2 significantly inhibited melanin synthesis, and produced less than 30% of baseline levels at both doses (10 and 50 µM) for 48 h compared to arbutin or PTU, respectively.

View Article: PubMed Central

ABSTRACT

In this study, we screened compounds with skin whitening properties and favorable safety profiles from a series of marine related natural products, which were isolated from Formosan soft coral Cladiella australis. Our results indicated that 4-(phenylsulfanyl)butan-2-one could successfully inhibit pigment generation processes in mushroom tyrosinase platform assay, probably through the suppression of tyrosinase activity to be a non-competitive inhibitor of tyrosinase. In cell-based viability examinations, it demonstrated low cytotoxicity on melanoma cells and other normal human cells. It exhibited stronger inhibitions of melanin production and tyrosinase activity than arbutin or 1-phenyl-2-thiourea (PTU). Also, we discovered that 4-(phenylsulfanyl)butan-2-one reduces the protein expressions of melanin synthesis-related proteins, including the microphthalmia-associated transcription factor (MITF), tyrosinase-related protein-1 (Trp-1), dopachrome tautomerase (DCT, Trp-2), and glycoprotein 100 (GP100). In an in vivo zebrafish model, it presented a remarkable suppression in melanogenesis after 48 h. In summary, our in vitro and in vivo biological assays showed that 4-(phenylsulfanyl)butan-2-one possesses anti-melanogenic properties that are significant in medical cosmetology.

No MeSH data available.