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 languageEnglish
Article number60
JournalPharmaceutics
Volume14
Issue number1
DOIs
Publication statusPublished - Jan 2022

Keywords

  • Host:guest
  • Hydrophobic
  • ITC
  • NMR
  • Pillararene
  • Supramolecular

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