Biomolecules & Therapeutics  
Development of S-Methylmethionine Sulfonium Derivatives and Their Skin-Protective Effect against Ultraviolet Exposure
Won-Serk Kim1, Wang-Kyun Kim1,2, Nahyun Choi2, Wonhee Suh3, Jinu Lee2, Dae-Duk Kim4, Ikyon Kim2,*, Jong-Hyuk Sung2,*
1Department of Dermatology, Kangbuk Samsung Hospital, Sungkyunkwan University School of Medicine, Seoul 03181,
2College of Pharmacy, Yonsei University, Incheon 21983,
3College of Pharmacy, Choongang University, Seoul 06974,
4College of Pharmacy, Seoul National University, Seoul 08826, Republic of Korea
E-mail: (Sung JH), (Kim I)
Tel: +82-32-749-4506 (Sung JH), +82-32-749-4162 (Kim I)
Received: May 18, 2017; Revised: August 30, 2017; Accepted: September 5, 2017; Published online: November 13, 2017.
© The Korean Society of Applied Pharmacology. All rights reserved.

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.
Keywords: S-methylmethionine derivatives, Proliferation, UVA/B protection, Reactive oxygen species

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