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

• Published in: Biomolecules & therapeutics Vol. 26; no. 3; pp. 306 - 312
• Main Authors: Kim, Won-Serk, Kim, Wang-Kyun, Choi, Nahyun, Suh, Wonhee, Lee, Jinu, Kim, Dae-Duk, Kim, Ikyon, Sung, Jong-Hyuk
• Format: Journal Article
• Language: English
• Published: Korea (South) The Korean Society of Applied Pharmacology 01.05.2018; 한국응용약물학회
• Subjects: Original; 약학; Reactive oxygen species; Proliferation; S-methylmethionine derivatives; UVA/B protection
• ISSN: 2005-4483; 1976-9148; 1976-9148; 2005-4483
• DOI: 10.4062/biomolther.2017.109

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 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.