Biomol Ther.  2018 May;26(3):306-312. 10.4062/biomolther.2017.109.

Development of S-Methylmethionine Sulfonium Derivatives and Their Skin-Protective Effect against Ultraviolet Exposure

• Kim WS
• Kim WK
• Choi N
• Suh W
• Lee J
• Kim DD
• Kim I
• Sung JH

• KMID: 2421740
• DOI: http://doi.org/10.4062/biomolther.2017.109

Abstract

In a previous study, we have demonstrated that S-methylmethionine sulfonium (SMMS) confers wound-healing and photoprotective effects on the skin, suggesting that SMMS can be used as a cosmetic raw material. However, it has an unpleasant odor. Therefore, in the present study, we synthesized odor-free SMMS derivatives by eliminating dimethyl sulfide, which is the cause of the unpleasant odor and identified two derivatives that exhibited skin-protective effects: one derivative comprised (2S,4S)- and (2R,4S)-2-phenylthiazolidine-4-carboxylic acid and the other comprised (2S,4R)-, (2S,4S)-, (2R,4R)-, and (2R,4S)-2-phenyl-1,3-thiazinane-4-carboxylic acid. We performed in vitro proliferation assays using human dermal fibroblasts (hDFs) and an immortalized human keratinocyte cell line (HaCaT). The two SMMS derivatives were shown to increase hDF and HaCaT cell proliferation as well as improve their survival by protecting against ultraviolet exposure. Moreover, the derivatives regulated the expression of collagen type I and MMP mRNAs against ultraviolet exposure in hDFs, suggesting that these derivatives can be developed as cosmetic raw materials.

Keyword

S-methylmethionine derivatives; Proliferation; UVA/B protection; Reactive oxygen species

MeSH Terms

Cell Line
Cell Proliferation
Collagen Type I
Fibroblasts
Humans
In Vitro Techniques
Keratinocytes
Odors
Reactive Oxygen Species
RNA, Messenger
Skin
Vitamin U*
Collagen Type I
RNA, Messenger
Reactive Oxygen Species
Vitamin U