Development of S-methylmethionine sulfonium derivatives and their skin-protective effect against ultraviolet exposure

Won Serk Kim, Wang Kyun Kim, Nahyun Choi, Wonhee Suh, Jinu Lee, Dae Duk Kim, Ikyon Kim, Jong Hyuk Sung

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5 Citations (Scopus)


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.

Original languageEnglish
Pages (from-to)306-312
Number of pages7
JournalBiomolecules and Therapeutics
Issue number3
Publication statusPublished - 2018 May

Bibliographical note

Funding Information:
This study was supported by a grant from the Korean Health Technology R&D Project, Ministry of Health & Welfare, Republic of Korea (HN14C0084). Jong-Hyuk Sung was partly supported by Yonsei University (2014-11-1658).

Publisher Copyright:
© 2018 The Korean Society of Applied Pharmacology.

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Molecular Medicine
  • Pharmacology
  • Drug Discovery


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