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Development of S-Methylmethionine Sulfonium Derivatives and Their Skin-Protective Effect against Ultraviolet Exposure
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...
Autores principales: | , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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The Korean Society of Applied Pharmacology
2018
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5933898/ https://www.ncbi.nlm.nih.gov/pubmed/29129045 http://dx.doi.org/10.4062/biomolther.2017.109 |
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author | Kim, Won-Serk Kim, Wang-Kyun Choi, Nahyun Suh, Wonhee Lee, Jinu Kim, Dae-Duk Kim, Ikyon Sung, Jong-Hyuk |
author_facet | Kim, Won-Serk Kim, Wang-Kyun Choi, Nahyun Suh, Wonhee Lee, Jinu Kim, Dae-Duk Kim, Ikyon Sung, Jong-Hyuk |
author_sort | Kim, Won-Serk |
collection | PubMed |
description | 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. |
format | Online Article Text |
id | pubmed-5933898 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2018 |
publisher | The Korean Society of Applied Pharmacology |
record_format | MEDLINE/PubMed |
spelling | pubmed-59338982018-05-04 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 Biomol Ther (Seoul) Original Article 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. The Korean Society of Applied Pharmacology 2018-05 2017-11-13 /pmc/articles/PMC5933898/ /pubmed/29129045 http://dx.doi.org/10.4062/biomolther.2017.109 Text en Copyright ©2018, The Korean Society of Applied Pharmacology http://creativecommons.org/licenses/by-nc/4.0/ This is an Open Access article distributed under the terms of the Creative Commons Attribution Non-Commercial License (http://creativecommons.org/licenses/by-nc/4.0/) which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited. |
spellingShingle | Original Article Kim, Won-Serk Kim, Wang-Kyun Choi, Nahyun Suh, Wonhee Lee, Jinu Kim, Dae-Duk Kim, Ikyon Sung, Jong-Hyuk Development of S-Methylmethionine Sulfonium Derivatives and Their Skin-Protective Effect against Ultraviolet Exposure |
title | Development of S-Methylmethionine Sulfonium Derivatives and Their Skin-Protective Effect against Ultraviolet Exposure |
title_full | Development of S-Methylmethionine Sulfonium Derivatives and Their Skin-Protective Effect against Ultraviolet Exposure |
title_fullStr | Development of S-Methylmethionine Sulfonium Derivatives and Their Skin-Protective Effect against Ultraviolet Exposure |
title_full_unstemmed | Development of S-Methylmethionine Sulfonium Derivatives and Their Skin-Protective Effect against Ultraviolet Exposure |
title_short | Development of S-Methylmethionine Sulfonium Derivatives and Their Skin-Protective Effect against Ultraviolet Exposure |
title_sort | development of s-methylmethionine sulfonium derivatives and their skin-protective effect against ultraviolet exposure |
topic | Original Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5933898/ https://www.ncbi.nlm.nih.gov/pubmed/29129045 http://dx.doi.org/10.4062/biomolther.2017.109 |
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