Synthesis of a New Water-Soluble Melatonin Derivative with Low Toxicity and a Strong Effect on Sleep Aid

[Image: see text] A new melatonin sulfonate derivative sodium 4-(3-(2-acetamidoethyl)-5-methoxy-1H-indol-1-yl) butane-1-sulfonate (MLTBS) with higher water solubility (695 times) and lower cytotoxicity than natural melatonin (MLT) was synthesized, yet with the same sleep aid function. The poor solub...

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Autores principales: Zhang, Jianghong, Yan, Xu, Tian, Yunpeng, Li, Wanyun, Wang, Haiyang, Li, Qinbin, Li, Yufei, Li, Zhu, Wu, Ting
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2020
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7114735/
https://www.ncbi.nlm.nih.gov/pubmed/32258885
http://dx.doi.org/10.1021/acsomega.9b04120
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author Zhang, Jianghong
Yan, Xu
Tian, Yunpeng
Li, Wanyun
Wang, Haiyang
Li, Qinbin
Li, Yufei
Li, Zhu
Wu, Ting
author_facet Zhang, Jianghong
Yan, Xu
Tian, Yunpeng
Li, Wanyun
Wang, Haiyang
Li, Qinbin
Li, Yufei
Li, Zhu
Wu, Ting
author_sort Zhang, Jianghong
collection PubMed
description [Image: see text] A new melatonin sulfonate derivative sodium 4-(3-(2-acetamidoethyl)-5-methoxy-1H-indol-1-yl) butane-1-sulfonate (MLTBS) with higher water solubility (695 times) and lower cytotoxicity than natural melatonin (MLT) was synthesized, yet with the same sleep aid function. The poor solubility of MLT in water has been improved with a simple chemical reaction, which solves the poor solubility of melatonin in water, overcoming the safety problem caused by adding organic reagents such as dimethyl sulfoxide (DMSO) and ethanol to increase the solubility. Moreover, the modified MLT still has the same sleep aid effect as the natural MLT and higher biological safety. As a novel potential drug for sleep aid, the new MLT derivative could also flourish the application and research of this molecule in medicine and biology.
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spelling pubmed-71147352020-04-03 Synthesis of a New Water-Soluble Melatonin Derivative with Low Toxicity and a Strong Effect on Sleep Aid Zhang, Jianghong Yan, Xu Tian, Yunpeng Li, Wanyun Wang, Haiyang Li, Qinbin Li, Yufei Li, Zhu Wu, Ting ACS Omega [Image: see text] A new melatonin sulfonate derivative sodium 4-(3-(2-acetamidoethyl)-5-methoxy-1H-indol-1-yl) butane-1-sulfonate (MLTBS) with higher water solubility (695 times) and lower cytotoxicity than natural melatonin (MLT) was synthesized, yet with the same sleep aid function. The poor solubility of MLT in water has been improved with a simple chemical reaction, which solves the poor solubility of melatonin in water, overcoming the safety problem caused by adding organic reagents such as dimethyl sulfoxide (DMSO) and ethanol to increase the solubility. Moreover, the modified MLT still has the same sleep aid effect as the natural MLT and higher biological safety. As a novel potential drug for sleep aid, the new MLT derivative could also flourish the application and research of this molecule in medicine and biology. American Chemical Society 2020-03-16 /pmc/articles/PMC7114735/ /pubmed/32258885 http://dx.doi.org/10.1021/acsomega.9b04120 Text en Copyright © 2020 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Zhang, Jianghong
Yan, Xu
Tian, Yunpeng
Li, Wanyun
Wang, Haiyang
Li, Qinbin
Li, Yufei
Li, Zhu
Wu, Ting
Synthesis of a New Water-Soluble Melatonin Derivative with Low Toxicity and a Strong Effect on Sleep Aid
title Synthesis of a New Water-Soluble Melatonin Derivative with Low Toxicity and a Strong Effect on Sleep Aid
title_full Synthesis of a New Water-Soluble Melatonin Derivative with Low Toxicity and a Strong Effect on Sleep Aid
title_fullStr Synthesis of a New Water-Soluble Melatonin Derivative with Low Toxicity and a Strong Effect on Sleep Aid
title_full_unstemmed Synthesis of a New Water-Soluble Melatonin Derivative with Low Toxicity and a Strong Effect on Sleep Aid
title_short Synthesis of a New Water-Soluble Melatonin Derivative with Low Toxicity and a Strong Effect on Sleep Aid
title_sort synthesis of a new water-soluble melatonin derivative with low toxicity and a strong effect on sleep aid
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7114735/
https://www.ncbi.nlm.nih.gov/pubmed/32258885
http://dx.doi.org/10.1021/acsomega.9b04120
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