New Non-Toxic N-alkyl Cholinium-Based Ionic Liquids as Excipients to Improve the Solubility of Poorly Water-Soluble Drugs

Autor:	Luís Raposo, José M. S. S. Esperança, Pedro V. Baptista, Daniela A.S. Agostinho, Patrícia M. Reis, Mário R. C. Soromenho, Alexandra R. Fernandes, Ana R. Jesus
Přispěvatelé:	LAQV@REQUIMTE, DQ - Departamento de Química, UCIBIO - Applied Molecular Biosciences Unit
Rok vydání:	2021
Předmět:	Mathematics(all) Bioavailability Physics and Astronomy (miscellaneous) Cytotoxicity General Mathematics Inorganic chemistry Oral drugs Nuclear Overhauser effect Ion ionic liquids chemistry.chemical_compound QA1-939 Computer Science (miscellaneous) oral drugs Solubility Dissolution Alkyl chemistry.chemical_classification Chemistry Diclofenac Sodium Ionic liquids Sulfonate Chemistry (miscellaneous) Drug delivery drug delivery Ionic liquid cytotoxicity bioavailability Mathematics
Zdroj:	Symmetry, Vol 13, Iss 2053, p 2053 (2021) Symmetry Volume 13 Issue 11 Repositório Científico de Acesso Aberto de Portugal Repositório Científico de Acesso Aberto de Portugal (RCAAP) instacron:RCAAP
ISSN:	2073-8994
DOI:	10.3390/sym13112053
Popis:	In this work, we prepared new biocompatible N-alkyl cholinium-based ionic liquids to be used as cosolvents to improve the solubility of poorly water-soluble drugs, namely, sodium diclofenac and paracetamol. In this set of ionic liquids, we intend to understand the effect of increasing the asymmetry of the ionic liquid cation/anion by growing the length of one of the alkyl chains attached to the nitrogen center/sulfonate center on the dissolution capacity of the ionic liquid. The addition of these new ionic liquids to water increased the dissolution capacity of the drugs up to four-times that in water, and improved the pharmacodynamic properties of these drugs, especially the case of sodium diclofenac. The intermolecular interactions between the drugs and ionic liquids were investigated by NMR. Two-dimensional 1H/1H nuclear overhauser effect spectroscopy (NOESY) revealed an interaction between sodium diclofenac and the alaninate anion from the [C2Ch]2[SucAla]. In the case of paracetamol and [C4Ch][C2SO3], it was possible to observe two intermolecular interactions between the hydroxyl group of paracetamol and two protons from the cation [C4Ch]+. Interestingly, the ionic liquid bearing a succinyl-DL-alaninate anion, [SucAla]2−, and a N-ethyl cholinium cation, [C2Ch]+, which presented the highest ability to dissolve sodium diclofenac, showed no cytotoxicity up to 500 mM. Therefore, this ionic liquid is a potential candidate for drug delivery applications.
Databáze:	OpenAIRE
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