Molecular Recognition by Pillar[5]arenes: Evidence for Simultaneous Electrostatic and Hydrophobic Interactions

The formation of inclusion complexes between alkylsulfonate guests and a cationic pillar[5]arene receptor in water was investigated by NMR and ITC techniques. The results show the formation of host-guest complexes stabilized by electrostatic interactions and hydrophobic effects with binding constant...

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Autores principales: Gómez-González, Borja, García-Río, Luis, Basílio, Nuno, Mejuto, Juan C., Simal-Gandara, Jesus
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8777861/
https://www.ncbi.nlm.nih.gov/pubmed/35056956
http://dx.doi.org/10.3390/pharmaceutics14010060
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author Gómez-González, Borja
García-Río, Luis
Basílio, Nuno
Mejuto, Juan C.
Simal-Gandara, Jesus
author_facet Gómez-González, Borja
García-Río, Luis
Basílio, Nuno
Mejuto, Juan C.
Simal-Gandara, Jesus
author_sort Gómez-González, Borja
collection PubMed
description The formation of inclusion complexes between alkylsulfonate guests and a cationic pillar[5]arene receptor in water was investigated by NMR and ITC techniques. The results show the formation of host-guest complexes stabilized by electrostatic interactions and hydrophobic effects with binding constants of up to 10(7) M(−1) for the guest with higher hydrophobic character. Structurally, the alkyl chain of the guest is included in the hydrophobic aromatic cavity of the macrocycle while the sulfonate groups are held in the multicationic portal by ionic interactions.
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spelling pubmed-87778612022-01-22 Molecular Recognition by Pillar[5]arenes: Evidence for Simultaneous Electrostatic and Hydrophobic Interactions Gómez-González, Borja García-Río, Luis Basílio, Nuno Mejuto, Juan C. Simal-Gandara, Jesus Pharmaceutics Article The formation of inclusion complexes between alkylsulfonate guests and a cationic pillar[5]arene receptor in water was investigated by NMR and ITC techniques. The results show the formation of host-guest complexes stabilized by electrostatic interactions and hydrophobic effects with binding constants of up to 10(7) M(−1) for the guest with higher hydrophobic character. Structurally, the alkyl chain of the guest is included in the hydrophobic aromatic cavity of the macrocycle while the sulfonate groups are held in the multicationic portal by ionic interactions. MDPI 2021-12-28 /pmc/articles/PMC8777861/ /pubmed/35056956 http://dx.doi.org/10.3390/pharmaceutics14010060 Text en © 2021 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
Gómez-González, Borja
García-Río, Luis
Basílio, Nuno
Mejuto, Juan C.
Simal-Gandara, Jesus
Molecular Recognition by Pillar[5]arenes: Evidence for Simultaneous Electrostatic and Hydrophobic Interactions
title Molecular Recognition by Pillar[5]arenes: Evidence for Simultaneous Electrostatic and Hydrophobic Interactions
title_full Molecular Recognition by Pillar[5]arenes: Evidence for Simultaneous Electrostatic and Hydrophobic Interactions
title_fullStr Molecular Recognition by Pillar[5]arenes: Evidence for Simultaneous Electrostatic and Hydrophobic Interactions
title_full_unstemmed Molecular Recognition by Pillar[5]arenes: Evidence for Simultaneous Electrostatic and Hydrophobic Interactions
title_short Molecular Recognition by Pillar[5]arenes: Evidence for Simultaneous Electrostatic and Hydrophobic Interactions
title_sort molecular recognition by pillar[5]arenes: evidence for simultaneous electrostatic and hydrophobic interactions
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8777861/
https://www.ncbi.nlm.nih.gov/pubmed/35056956
http://dx.doi.org/10.3390/pharmaceutics14010060
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