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Novel enterobactin analogues as potential therapeutic chelating agents: Synthesis, thermodynamic and antioxidant studies

A series of novel hexadentate enterobactin analogues, which contain three catechol chelating moieties attached to different molecular scaffolds with flexible alkyl chain lengths, were prepared. The solution thermodynamic stabilities of the complexes with uranyl, ferric(III), and zinc(II) ions were t...

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Autores principales: Zhang, Qingchun, Jin, Bo, Shi, Zhaotao, Wang, Xiaofang, Liu, Qiangqiang, Lei, Shan, Peng, Rufang
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group 2016
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5037427/
https://www.ncbi.nlm.nih.gov/pubmed/27671769
http://dx.doi.org/10.1038/srep34024
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author Zhang, Qingchun
Jin, Bo
Shi, Zhaotao
Wang, Xiaofang
Liu, Qiangqiang
Lei, Shan
Peng, Rufang
author_facet Zhang, Qingchun
Jin, Bo
Shi, Zhaotao
Wang, Xiaofang
Liu, Qiangqiang
Lei, Shan
Peng, Rufang
author_sort Zhang, Qingchun
collection PubMed
description A series of novel hexadentate enterobactin analogues, which contain three catechol chelating moieties attached to different molecular scaffolds with flexible alkyl chain lengths, were prepared. The solution thermodynamic stabilities of the complexes with uranyl, ferric(III), and zinc(II) ions were then investigated. The hexadentate ligands demonstrate effective binding ability to uranyl ion, and the average uranyl affinities are two orders of magnitude higher than 2,3-dihydroxy-N(1),N(4)-bis[(1,2-hydroxypyridinone-6-carboxamide)ethyl]terephthalamide [TMA(2Li-1,2-HOPO)(2)] ligand with similar denticity. The high affinity of hexadentate ligands could be due to the presence of the flexible scaffold, which favors the geometric agreement between the ligand and the uranyl coordination preference. The hexadentate ligands also exhibit higher antiradical efficiency than butylated hydroxyanisole (BHA). These results provide a basis for further studies on the potential applications of hexadentate ligands as therapeutic chelating agents.
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spelling pubmed-50374272016-09-30 Novel enterobactin analogues as potential therapeutic chelating agents: Synthesis, thermodynamic and antioxidant studies Zhang, Qingchun Jin, Bo Shi, Zhaotao Wang, Xiaofang Liu, Qiangqiang Lei, Shan Peng, Rufang Sci Rep Article A series of novel hexadentate enterobactin analogues, which contain three catechol chelating moieties attached to different molecular scaffolds with flexible alkyl chain lengths, were prepared. The solution thermodynamic stabilities of the complexes with uranyl, ferric(III), and zinc(II) ions were then investigated. The hexadentate ligands demonstrate effective binding ability to uranyl ion, and the average uranyl affinities are two orders of magnitude higher than 2,3-dihydroxy-N(1),N(4)-bis[(1,2-hydroxypyridinone-6-carboxamide)ethyl]terephthalamide [TMA(2Li-1,2-HOPO)(2)] ligand with similar denticity. The high affinity of hexadentate ligands could be due to the presence of the flexible scaffold, which favors the geometric agreement between the ligand and the uranyl coordination preference. The hexadentate ligands also exhibit higher antiradical efficiency than butylated hydroxyanisole (BHA). These results provide a basis for further studies on the potential applications of hexadentate ligands as therapeutic chelating agents. Nature Publishing Group 2016-09-27 /pmc/articles/PMC5037427/ /pubmed/27671769 http://dx.doi.org/10.1038/srep34024 Text en Copyright © 2016, The Author(s) http://creativecommons.org/licenses/by/4.0/ This work is licensed under a Creative Commons Attribution 4.0 International License. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in the credit line; if the material is not included under the Creative Commons license, users will need to obtain permission from the license holder to reproduce the material. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/
spellingShingle Article
Zhang, Qingchun
Jin, Bo
Shi, Zhaotao
Wang, Xiaofang
Liu, Qiangqiang
Lei, Shan
Peng, Rufang
Novel enterobactin analogues as potential therapeutic chelating agents: Synthesis, thermodynamic and antioxidant studies
title Novel enterobactin analogues as potential therapeutic chelating agents: Synthesis, thermodynamic and antioxidant studies
title_full Novel enterobactin analogues as potential therapeutic chelating agents: Synthesis, thermodynamic and antioxidant studies
title_fullStr Novel enterobactin analogues as potential therapeutic chelating agents: Synthesis, thermodynamic and antioxidant studies
title_full_unstemmed Novel enterobactin analogues as potential therapeutic chelating agents: Synthesis, thermodynamic and antioxidant studies
title_short Novel enterobactin analogues as potential therapeutic chelating agents: Synthesis, thermodynamic and antioxidant studies
title_sort novel enterobactin analogues as potential therapeutic chelating agents: synthesis, thermodynamic and antioxidant studies
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5037427/
https://www.ncbi.nlm.nih.gov/pubmed/27671769
http://dx.doi.org/10.1038/srep34024
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