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Deep Eutectic Solvents as Agents for Improving the Solubility of Edaravone: Experimental and Theoretical Considerations.
Jelinski, Tomasz; Przybylek, Maciej; Mianowana, Magdalena; Misiak, Kinga; Cysewski, Piotr.
Afiliação
  • Jelinski T; Department of Physical Chemistry, Collegium Medicum of Bydgoszcz, Nicolaus Copernicus University in Torun, Kurpinskiego 5, 85-096 Bydgoszcz, Poland.
  • Przybylek M; Department of Physical Chemistry, Collegium Medicum of Bydgoszcz, Nicolaus Copernicus University in Torun, Kurpinskiego 5, 85-096 Bydgoszcz, Poland.
  • Mianowana M; Department of Physical Chemistry, Collegium Medicum of Bydgoszcz, Nicolaus Copernicus University in Torun, Kurpinskiego 5, 85-096 Bydgoszcz, Poland.
  • Misiak K; Department of Physical Chemistry, Collegium Medicum of Bydgoszcz, Nicolaus Copernicus University in Torun, Kurpinskiego 5, 85-096 Bydgoszcz, Poland.
  • Cysewski P; Department of Physical Chemistry, Collegium Medicum of Bydgoszcz, Nicolaus Copernicus University in Torun, Kurpinskiego 5, 85-096 Bydgoszcz, Poland.
Molecules ; 29(6)2024 Mar 12.
Article em En | MEDLINE | ID: mdl-38542898
ABSTRACT
In this study, both practical and theoretical aspects of the solubility of edaravone (EDA) in Deep Eutectic Solvents (DESs) were considered. The solubility of edaravone in some media, including water, can be limited, which creates the need for new efficient and environmentally safe solvents. The solubility of EDA was measured spectrophotometrically and the complex intermolecular interactions within the systems were studied with the COSMO-RS framework. Of the four studied DES systems, three outperformed the most efficient classical organic solvent, namely dichloromethane, with the DES comprising choline chloride and triethylene glycol, acting as hydrogen bond donor (HBD), in a 12 molar proportion yielding the highest solubility of EDA. Interestingly, the addition of a specific amount of water further increased EDA solubility. Theoretical analysis revealed that in pure water or solutions with high water content, EDA stacking is responsible for self-aggregation and lower solubility. On the other hand, the presence of HBDs leads to the formation of intermolecular clusters with EDA, reducing self-aggregation. However, in the presence of a stoichiometric amount of water, a three-molecular EDA-HBD-water complex is formed, which explains why water can also act as a co-solvent. The high probability of formation of this type of complexes is related to the high affinity of the components, which exceeds all other possible complexes.
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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Revista: Molecules Assunto da revista: BIOLOGIA Ano de publicação: 2024 Tipo de documento: Article País de afiliação: Polônia

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Revista: Molecules Assunto da revista: BIOLOGIA Ano de publicação: 2024 Tipo de documento: Article País de afiliação: Polônia