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Chelating Silicone Dendrons: Trying to Impact Organisms by Disrupting Ions at Interfaces

The viability of pathogens at interfaces can be disrupted by the presence of (cationic) charge and chelating groups. We report on the synthesis of silicone dendrimers and linear polymers based on a motif of hexadentate ligands with the ability to capture and deliver metal ions. Mono-, di- or trialko...

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Autores principales: Melendez-Zamudio, Miguel, Chavda, Kevina, Brook, Michael A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8954278/
https://www.ncbi.nlm.nih.gov/pubmed/35335233
http://dx.doi.org/10.3390/molecules27061869
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author Melendez-Zamudio, Miguel
Chavda, Kevina
Brook, Michael A.
author_facet Melendez-Zamudio, Miguel
Chavda, Kevina
Brook, Michael A.
author_sort Melendez-Zamudio, Miguel
collection PubMed
description The viability of pathogens at interfaces can be disrupted by the presence of (cationic) charge and chelating groups. We report on the synthesis of silicone dendrimers and linear polymers based on a motif of hexadentate ligands with the ability to capture and deliver metal ions. Mono-, di- or trialkoxysilanes are converted in G1 to analogous vinylsilicones and then, iteratively using the Piers-Rubinsztajn reaction and hydrosilylation, each vinyl group is transformed into a trivinyl cluster at G2. The thiol-ene reaction with cysteamine or 3-mercaptopropionic acid and the trivinyl cluster leads to hexadentate ligands 3 × N–S or 3 × HOOC–S. The compounds were shown to effectively capture a variety of metals ions. Copper ion chelation was pursued in more detail, because of its toxicity. On average, metal ions form chelates with 2.4 of the three ligands in a cluster. Upon chelation, viscous oils are converted to (very) soft elastomers. Most of the ions could be stripped from the elastomers using aqueous EDTA solutions, demonstrating the ability of the silicones to both sequester and deliver ions. However, complete ion removal is not observed; at equilibrium, the silicones remain ionically crosslinked.
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spelling pubmed-89542782022-03-26 Chelating Silicone Dendrons: Trying to Impact Organisms by Disrupting Ions at Interfaces Melendez-Zamudio, Miguel Chavda, Kevina Brook, Michael A. Molecules Article The viability of pathogens at interfaces can be disrupted by the presence of (cationic) charge and chelating groups. We report on the synthesis of silicone dendrimers and linear polymers based on a motif of hexadentate ligands with the ability to capture and deliver metal ions. Mono-, di- or trialkoxysilanes are converted in G1 to analogous vinylsilicones and then, iteratively using the Piers-Rubinsztajn reaction and hydrosilylation, each vinyl group is transformed into a trivinyl cluster at G2. The thiol-ene reaction with cysteamine or 3-mercaptopropionic acid and the trivinyl cluster leads to hexadentate ligands 3 × N–S or 3 × HOOC–S. The compounds were shown to effectively capture a variety of metals ions. Copper ion chelation was pursued in more detail, because of its toxicity. On average, metal ions form chelates with 2.4 of the three ligands in a cluster. Upon chelation, viscous oils are converted to (very) soft elastomers. Most of the ions could be stripped from the elastomers using aqueous EDTA solutions, demonstrating the ability of the silicones to both sequester and deliver ions. However, complete ion removal is not observed; at equilibrium, the silicones remain ionically crosslinked. MDPI 2022-03-14 /pmc/articles/PMC8954278/ /pubmed/35335233 http://dx.doi.org/10.3390/molecules27061869 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Melendez-Zamudio, Miguel
Chavda, Kevina
Brook, Michael A.
Chelating Silicone Dendrons: Trying to Impact Organisms by Disrupting Ions at Interfaces
title Chelating Silicone Dendrons: Trying to Impact Organisms by Disrupting Ions at Interfaces
title_full Chelating Silicone Dendrons: Trying to Impact Organisms by Disrupting Ions at Interfaces
title_fullStr Chelating Silicone Dendrons: Trying to Impact Organisms by Disrupting Ions at Interfaces
title_full_unstemmed Chelating Silicone Dendrons: Trying to Impact Organisms by Disrupting Ions at Interfaces
title_short Chelating Silicone Dendrons: Trying to Impact Organisms by Disrupting Ions at Interfaces
title_sort chelating silicone dendrons: trying to impact organisms by disrupting ions at interfaces
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8954278/
https://www.ncbi.nlm.nih.gov/pubmed/35335233
http://dx.doi.org/10.3390/molecules27061869
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AT brookmichaela chelatingsiliconedendronstryingtoimpactorganismsbydisruptingionsatinterfaces