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

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

doi:10.4062/biomolther.2017.109

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

Biomolecules & therapeutics, v.26 no.3, 2018년, pp.306 - 312

Kim, Won-Serk (Department of Dermatology, Kangbuk Samsung Hospital, Sungkyunkwan University School of Medicine) , Kim, Wang-Kyun (Department of Dermatology, Kangbuk Samsung Hospital, Sungkyunkwan University School of Medicine) , Choi, Nahyun (College of Pharmacy, Yonsei University) , Suh, Wonhee (College of Pharmacy, Choongang University) , Lee, Jinu (College of Pharmacy, Yonsei University) , Kim, Dae-Duk (College of Pharmacy, Seoul National University) , Kim, Ikyon (College of Pharmacy, Yonsei University) , Sung, Jong-Hyuk (College of Pharmacy, Yonsei University)

Abstract ▼ AI-Helper

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.

주제어

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가설 설정

Effect of compounds 15 and 16 in an immortalized human keratinocyte cell line (HaCaT). (A) Compound 15 did not increase HaCaT cell proliferation. (B) Compound 16 increased HaCaT cell proliferation in a dose-dependent manner.

제안 방법

To increase SMMS stability, we synthesized 50 SMMS derivatives and screened their proliferative and UVB-protective effects on hDFs. As shown in Fig.

대상 데이터

The culture plate lid was removed, and cells were irradiated (UVA: 7 J/ cm²; UVB: 120 mJ/cm² ) in a dark box. As the UVA irradiation source, a UVA lamp (TUV 15W/G15 T8) purchased from Philips (Groningen, The Netherlands) was used. The UVB irradiation apparatus (BLE-1T158) was obtained from Spectronics (Westbury, NY, USA).

데이터처리

The statistical significance of differences among groups was tested using a Student’s t-test, and p<0.05, p<0.01, and p<0.001 were considered as significant.

성능/효과

2; UVA dose: 7 J/cm² ). These results suggested that SMMS derivatives increased hDF survival and proliferation and protected them against UV irradiation by regulating the expression of collagen type I and MMPs.

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