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

Borja Gómez-González; Luis García-Río; Nuno Basílio; Juan C. Mejuto; Jesus Simal-Gandara

doi:10.3390/pharmaceutics14010060

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

Borja Gómez-González, Luis García-Río, Nuno Basílio, Juan C. Mejuto, Jesus Simal-Gandara

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Abstract

The formation of inclusion complexes between alkylsulfonate guests and a cationic pil-lar[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 10⁷ 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.

Original language	English
Article number	60
Journal	Pharmaceutics
Volume	14
Issue number	1
DOIs	https://doi.org/10.3390/pharmaceutics14010060
Publication status	Published - Jan 2022

Keywords

Host:guest
Hydrophobic
ITC
NMR
Pillararene
Supramolecular

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pharmaceutics-14-00060Final published version, 2.9 MBLicence: CC BY

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abstract = "The formation of inclusion complexes between alkylsulfonate guests and a cationic pil-lar[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 107 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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AU - Gómez-González, Borja

AU - García-Río, Luis

AU - Basílio, Nuno

AU - Mejuto, Juan C.

AU - Simal-Gandara, Jesus

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AB - The formation of inclusion complexes between alkylsulfonate guests and a cationic pil-lar[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 107 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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KW - Hydrophobic

KW - ITC

KW - NMR

KW - Pillararene

KW - Supramolecular

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JO - Pharmaceutics

JF - Pharmaceutics

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ER -

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

Abstract

Keywords

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