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Helically shaped cation receptor: design, synthesis, characterisation and first application to ion transport

The methyl ester of 8-oxo-8H-indeno[2′,1′:7,8]naphtho[1,2-b]thiophene-2-carboxylic acid (1) and its corresponding PEGylated ester were synthesised and fully characterised. X-ray diffraction studies on (1) confirmed the helical structure of the receptor and that it is self-assembled into layers by π–...

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Autores principales: Boufroura, Hamza, Plais, Romain, Poyer, Salomé, Gaucher, Anne, Marrot, Jérome, Clavier, Gilles, Legrand, François-Xavier, Huin, Cécile, Guégan, Philippe, Prim, Damien, Salpin, Jean-Yves
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9056421/
https://www.ncbi.nlm.nih.gov/pubmed/35520653
http://dx.doi.org/10.1039/d0ra05519k
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author Boufroura, Hamza
Plais, Romain
Poyer, Salomé
Gaucher, Anne
Marrot, Jérome
Clavier, Gilles
Legrand, François-Xavier
Huin, Cécile
Guégan, Philippe
Prim, Damien
Salpin, Jean-Yves
author_facet Boufroura, Hamza
Plais, Romain
Poyer, Salomé
Gaucher, Anne
Marrot, Jérome
Clavier, Gilles
Legrand, François-Xavier
Huin, Cécile
Guégan, Philippe
Prim, Damien
Salpin, Jean-Yves
author_sort Boufroura, Hamza
collection PubMed
description The methyl ester of 8-oxo-8H-indeno[2′,1′:7,8]naphtho[1,2-b]thiophene-2-carboxylic acid (1) and its corresponding PEGylated ester were synthesised and fully characterised. X-ray diffraction studies on (1) confirmed the helical structure of the receptor and that it is self-assembled into layers by π–π interactions. An in-depth study by DFT calculations and MS experiments (ESI-MS, MS/MS, IMRPD and ESI-IMS-MS) was carried out between (1) and the physiological cation K(+). The formation of supramolecular complexes between (1) and K(+) with different stoichiometries was demonstrated and the cation K(+) preferentially interacts with the oxygen atoms of the carbonyl bond of the ketone and ester groups and the sulphur atom of the heterocycle. The ability of the two synthesized aromatic architectures to transport ions across a model lipid membrane has been studied by electrophysiology experiments. The formation of pores was observed, even at nanomolar concentrations. Since the PEGylated molecule showed more regular pore definitions than the hydrophobic molecule, the introduction of a polar hydrophilic chain made it possible to control the orientation of the aromatic architectures within the membrane.
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spelling pubmed-90564212022-05-04 Helically shaped cation receptor: design, synthesis, characterisation and first application to ion transport Boufroura, Hamza Plais, Romain Poyer, Salomé Gaucher, Anne Marrot, Jérome Clavier, Gilles Legrand, François-Xavier Huin, Cécile Guégan, Philippe Prim, Damien Salpin, Jean-Yves RSC Adv Chemistry The methyl ester of 8-oxo-8H-indeno[2′,1′:7,8]naphtho[1,2-b]thiophene-2-carboxylic acid (1) and its corresponding PEGylated ester were synthesised and fully characterised. X-ray diffraction studies on (1) confirmed the helical structure of the receptor and that it is self-assembled into layers by π–π interactions. An in-depth study by DFT calculations and MS experiments (ESI-MS, MS/MS, IMRPD and ESI-IMS-MS) was carried out between (1) and the physiological cation K(+). The formation of supramolecular complexes between (1) and K(+) with different stoichiometries was demonstrated and the cation K(+) preferentially interacts with the oxygen atoms of the carbonyl bond of the ketone and ester groups and the sulphur atom of the heterocycle. The ability of the two synthesized aromatic architectures to transport ions across a model lipid membrane has been studied by electrophysiology experiments. The formation of pores was observed, even at nanomolar concentrations. Since the PEGylated molecule showed more regular pore definitions than the hydrophobic molecule, the introduction of a polar hydrophilic chain made it possible to control the orientation of the aromatic architectures within the membrane. The Royal Society of Chemistry 2020-08-27 /pmc/articles/PMC9056421/ /pubmed/35520653 http://dx.doi.org/10.1039/d0ra05519k Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Boufroura, Hamza
Plais, Romain
Poyer, Salomé
Gaucher, Anne
Marrot, Jérome
Clavier, Gilles
Legrand, François-Xavier
Huin, Cécile
Guégan, Philippe
Prim, Damien
Salpin, Jean-Yves
Helically shaped cation receptor: design, synthesis, characterisation and first application to ion transport
title Helically shaped cation receptor: design, synthesis, characterisation and first application to ion transport
title_full Helically shaped cation receptor: design, synthesis, characterisation and first application to ion transport
title_fullStr Helically shaped cation receptor: design, synthesis, characterisation and first application to ion transport
title_full_unstemmed Helically shaped cation receptor: design, synthesis, characterisation and first application to ion transport
title_short Helically shaped cation receptor: design, synthesis, characterisation and first application to ion transport
title_sort helically shaped cation receptor: design, synthesis, characterisation and first application to ion transport
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9056421/
https://www.ncbi.nlm.nih.gov/pubmed/35520653
http://dx.doi.org/10.1039/d0ra05519k
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