Improvement of New Dianionic Ionic Liquids vs Monoanionic in Solubility of Poorly Water-Soluble Drugs

Agostinho, Daniela A.S.; Jesus, Ana Rita; Silva, Ana B. P.; Esperança, José M. S. S.; Paiva, Alexandre; Duarte, Ana Rita C.; Reis, Pedro

doi:10.1016/j.xphs.2021.01.014

Cited by 12 publications

(6 citation statements)

References 26 publications

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“…The use of ILs significantly improves the solubility of drugs compared with the use of aqueous solutions. The solubilities of ibuprofen and piroxicam in dianionic ILs are up to 300-and 480-fold higher than in water, respectively (Figure 3B) [34]. Recently, several bio-ILs, such as choline-containing amino acids, carboxylic acids, and fatty acids, have been used to improve drug solubility [1,2].…”

Section: Drug Solubilizersmentioning

confidence: 99%

Recent Advances in Biocompatible Ionic Liquids in Drug Formulation and Delivery

et al. 2023

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The development of effective drug formulations and delivery systems for newly developed or marketed drug molecules remains a significant challenge. These drugs can exhibit polymorphic conversion, poor bioavailability, and systemic toxicity, and can be difficult to formulate with traditional organic solvents due to acute toxicity. Ionic liquids (ILs) are recognized as solvents that can improve the pharmacokinetic and pharmacodynamic properties of drugs. ILs can address the operational/functional challenges associated with traditional organic solvents. However, many ILs are non-biodegradable and inherently toxic, which is the most significant challenge in developing IL-based drug formulations and delivery systems. Biocompatible ILs comprising biocompatible cations and anions mainly derived from bio-renewable sources are considered a green alternative to both conventional ILs and organic/inorganic solvents. This review covers the technologies and strategies developed to design biocompatible ILs, focusing on the design of biocompatible IL-based drug formulations and delivery systems, and discusses the advantages of these ILs in pharmaceutical and biomedical applications. Furthermore, this review will provide guidance on transitioning to biocompatible ILs rather than commonly used toxic ILs and organic solvents in fields ranging from chemical synthesis to pharmaceutics.

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Section: Drug Solubilizersmentioning

confidence: 99%

Recent Advances in Biocompatible Ionic Liquids in Drug Formulation and Delivery

et al. 2023

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“…8A). 8,260 For example, a small amount of choline lysinate ([Ch][Lys]) could significantly increase the solubility of ferulic acid and puerarin, because [Ch][Lys] would improve the solubility of hydrophobic substances. 261 CAGE also improved the bioavailability of sorafenib (a hydrophobic drug) by increasing its solubility though oral delivery.…”

Section: Application Of Ils In Delivery Systemsmentioning

confidence: 99%

Ionic liquids revolutionizing biomedicine: recent advances and emerging opportunities

Hu,

Xing,

Yue

et al. 2023

Chem. Soc. Rev.

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“…Four new dianionic ILs containing a succinyl-DLalaninate anion keeping some N-alkyl cholinium cation were also synthesized (Figure 1c). Our research group already reported that dianionic ionic liquids based on ammonium cations and carboxylic and/or phosphonate anions are able to increase the solubility of ibuprofen and piroxicam, but all of them presented an IC50 between 55-120 mM [22,23].…”

Section: Introductionmentioning

confidence: 99%

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

et al. 2021

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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.

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Improvement of New Dianionic Ionic Liquids vs Monoanionic in Solubility of Poorly Water-Soluble Drugs

Cited by 12 publications

References 26 publications

Recent Advances in Biocompatible Ionic Liquids in Drug Formulation and Delivery

Recent Advances in Biocompatible Ionic Liquids in Drug Formulation and Delivery

Ionic liquids revolutionizing biomedicine: recent advances and emerging opportunities

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

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