D-tyrosine adds an anti-melanogenic effect to cosmetic peptides

Jisu Park,Hyun-Kuk Song,Inn-Oc Han,Eok-Soo Oh,Bohee Jang,Hyejung Jung

doi:10.1038/s41598-019-57159-3

Jisu Park, Hyun-Kuk Song + Show 4 more

Open Access

https://doi.org/10.1038/s41598-019-57159-3

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Abstract

D-tyrosine is known to negatively regulate melanin synthesis by inhibiting tyrosinase activity. Here, we further reveal that peptides containing terminal D-tyrosine can reduce the melanin contents of human melanocytes. The addition of D-tyrosine to the terminus of the commercial anti-wrinkle peptide, pentapeptide-18 endowed the peptide with the ability to reduce the melanin content and tyrosinase activity in human MNT-1 melanoma cells and primary melanocytes. Consistently, terminal D-tyrosine-containing pentapeptide-18 inhibited the melanogenesis induced by α-MSH treatment or UV irradiation of MNT-1 cells and reduced melanin synthesis in the epidermal basal layer of a 3D human skin model. Furthermore, the addition of D-tyrosine to an anti-aging peptide (GEKG) or an anti-inflammatory peptide (GHK) endowed these short peptides with anti-melanogenic effects without altering their intrinsic effects. Together, these data suggest that the addition of D-tyrosine at the terminus of a short cosmetic peptide adds an anti-melanogenic effect to its intrinsic cosmetic effect. Our work offers a novel means of generating dual-function cosmetic peptides.

Highlights

D-tyrosine is known to negatively regulate melanin synthesis by inhibiting tyrosinase activity
We recently reported that D-tyrosine, the enantiomer of L-tyrosine, suppresses melanogenesis induced by α-MSH treatment or UV irradiation, two key inducers of melanogenesis, in melanocytes by inhibiting the enzymatic activity of tyrosinase[18]
We synthesized pentapeptide-18 peptides in which we either replaced L-tyrosine with D-tyrosine at the N-terminus or added a L- or D-tyrosine at the C-terminus (Fig. 1A) and treated human melanoma MNT-1 cells with various doses of each peptide (Fig. 1B)

Summary

Introduction

D-tyrosine is known to negatively regulate melanin synthesis by inhibiting tyrosinase activity. The addition of D-tyrosine to the terminus of the commercial anti-wrinkle peptide, pentapeptide-18 endowed the peptide with the ability to reduce the melanin content and tyrosinase activity in human MNT-1 melanoma cells and primary melanocytes. Terminal D-tyrosine-containing pentapeptide-18 inhibited the melanogenesis induced by α-MSH treatment or UV irradiation of MNT-1 cells and reduced melanin synthesis in the epidermal basal layer of a 3D human skin model. As tyrosinase is a key enzyme that catalyzes a rate-limiting step of melanin synthesis, numerous inhibitors that target tyrosinase have been investigated for their ability to inhibit this process These include well-known tyrosinase inhibitors, such as hydroquinone[8], arbutin[9], kojic acid[10], and salicylic acid[11]. We investigated whether D-tyrosine-containing cosmetic peptides can regulate melanin synthesis in melanoma cells and melanocytes.

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