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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...

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Autores principales: Kim, Won-Serk, Kim, Wang-Kyun, Choi, Nahyun, Suh, Wonhee, Lee, Jinu, Kim, Dae-Duk, Kim, Ikyon, Sung, Jong-Hyuk
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Korean Society of Applied Pharmacology 2018
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.
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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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