Solubilities of pharmaceutical and bioactive compounds in trihexyl(tetradecyl)phosphonium chloride ionic liquid

Faria, Ricardo A.; Bogel‐Łukasik, Ewa

doi:10.1016/j.fluid.2015.03.053

Cited by 23 publications

(12 citation statements)

References 38 publications

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“…Tables and show the solid–liquid equilibria results, temperatures, T , versus x 1 (mole fraction of the solute), for the studied systems. The commonly discovered result is confirmed in this study, namely a slight increase of temperature leads to a slight increase of solubility. ,− The presented phase diagrams are theoretical solid–liquid phase envelopes. The experimental method did not allow a determination of the eutectic points.…”

Section: Resultssupporting

confidence: 83%

“…Because of the diverse nature of ILs, these can have several potential interactions with the compounds, namely Coulombic, dispersive, hydrogen bonding, π–π, n−π, dipolar, and ionic/charge–charge. Nevertheless, in previous studies it has been concluded that the major factors affecting the solubility are the polarity of the ionic liquids and their ability to form hydrogen bonds. ,− Isoniazid being a more hydrophilic compound exhibits enhanced solubility in hydrophilic ILs, that is, negative deviations from ideality, while pyrazinecarboxamide, being slightly less hydrophilic than isoniazid, exhibits enhanced solubility even in slightly more hydrophobic ILs, such as the ones with trifluoromethanesulfonate, but not for highly hydrophobic ILs, such as [C 10 mim][OTf] . In this work, the experimental solubility data provided for pharmaceutical and bioactive compounds are described by correlation equations with an adequate σ T .…”

Section: Resultsmentioning

confidence: 99%

“…The solubility of TB medicines, such as pyrazinecarboxamide (IUPAC name: pyrazine-2-carboxamide) and isoniazid (IUPAC name: isonicotinohydrazide) have been reported for ammonium, phosphonium, , and some imidazolium ,, ILs. This work aimed to provide more solubility data on two antibiotic medicines used in the treatment of TB, namely pyrazinecarboxamide and isoniazid, in several ILs composed by imidazolium cations, to see the effect of the anion (tetrafluoroborate [BF 4 ], hexafluorophosphate [PF 6 ], trifluoromethanesulfonate [OTf]), as well as influence of the alkyl chain length of the cation by investigating 1-alkyl-3-methylimidazolium trifluoromethanesulfonate [C n mim] [OTf], ( n = 4, 8) and comparison with n = 10. , The molecular structures for the antitubercular compounds and the ionic liquids that were used in this work are presented in Figure .…”

Section: Introductionmentioning

confidence: 99%

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Solubility Data as a Response for a Challenge for Formulation Chemists: Imidazolium-Based Ionic Liquids and Antitubercular Antibiotic Medicines

et al. 2016

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The evolution of technology is directed to reduce industrial waste from chemical processes to zero. In the past decade interest in ionic liquids (ILs) has grown, and they have been recognized as potential substitutes for volatile organic solvents used in certain chemical processes, including those in the pharmaceutical industry. Following this increasing interest and because ILs can have a great potential for the pharmaceutical industry, we tested the solubility of two antitubercular medicines, pyrazinecarboxamide and isoniazid, in imidazolium ionic liquids, namely [C4mim][BF4], [C4mim][PF6], [C4mim][OTf], and [C8mim][OTf], in the range of 279.98 to 417.05 K. Both drugs exhibited an improved solubility in [C4mim][BF4] than in the other studied ILs. The solutes had an enhanced solubility in more hydrophilic ILs, such as [C4mim][BF4] and [C4mim][PF6]. The solubility decreased in ILs containing the hydrophobic anion trifluoromethanesulfonate and with the increasing alkyl chain length in the cation. The solid–liquid phase equilibria of all investigated systems were described using six different correlation equations. The satisfactory results which revealed a good description with an acceptable standard deviation temperature range were collected for isoniazid or pyrazinecarboxamide in [C4mim][PF6], [C4mim][OTf] and [C8mim][OTf]. Comparison to solubility in NTf2 and [C10mim][OTf] was provided.

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Section: Resultssupporting

confidence: 83%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Solubility Data as a Response for a Challenge for Formulation Chemists: Imidazolium-Based Ionic Liquids and Antitubercular Antibiotic Medicines

et al. 2016

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“…In the case of the IL anion [ 17 , 61 ], a more complex phenomenon occurs, although specific API-ILs interactions are considered as driving forces for enhanced dissolution of hydrophobic drugs when compared with their solubility in water. In the past few years, a significant number of studies have risen in the literature reporting the potential as solubility enhancers of ILs comprising ammonium- and phosphonium-based cations [ 17 , 64 , 65 , 66 , 67 ] as well as structures with cheaper and more biodegradable profiles [ 30 , 68 , 69 ].…”

Section: Ils Used To Improve the Solubility (Bioavailability) Of Pharmaceuticalsmentioning

confidence: 99%

Advances Brought by Hydrophilic Ionic Liquids in Fields Involving Pharmaceuticals

et al. 2021

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The negligible volatility and high tunable nature of ionic liquids (ILs) have been the main drivers of their investigation in a wide diversity of fields, among which is their application in areas involving pharmaceuticals. Although most literature dealing with ILs is still majorly devoted to hydrophobic ILs, evidence on the potential of hydrophilic ILs have been increasingly provided in the past decade, viz., ILs with improved therapeutic efficiency and bioavailability, ILs with the ability to increase drugs' aqueous solubility, ILs with enhanced extraction performance for pharmaceuticals when employed in biphasic systems and other techniques, and ILs displaying low eco/cyto/toxicity and beneficial biological activities. Given their relevance, it is here overviewed the applications of hydrophilic ILs in fields involving pharmaceuticals, particularly focusing on achievements and advances witnessed during the last decade. The application of hydrophilic ILs within fields involving pharmaceuticals is here critically discussed according to four categories: (i) to improve pharmaceuticals solubility, envisioning improved bioavailability; (ii) as IL-based drug delivery systems; (iii) as pretreatment techniques to improve analytical methods performance dealing with pharmaceuticals, and (iv) in the recovery and purification of pharmaceuticals using IL-based systems. Key factors in the selection of appropriate ILs are identified. Insights and perspectives to bring renewed and effective solutions involving ILs able to compete with current commercial technologies are finally provided.

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“…In recent years, ionic liquids have been investigated extensively in different applications, such as reaction media (Melo et al, 2012), catalysts (Crosthwaite et al, 2008;Bogel-Łukasik et al, 2010), synthesis (Cooper et al, 2004) and separation science, because of the excellent properties (Faria and Bogel-Łukasik, 2015). The main application of ionic liquids was acting as reaction solvents in successful extraction and separation of different bioactive compounds from plant materials, including lignans (Prado et al, 2016), quinones (Liu et al, 2013), alkaloids (Lu et al, 2008) and flavonoids compounds .…”

Section: Introductionmentioning

confidence: 99%

Simultaneous synergistic microwave–ultrasonic extraction and hydrolysis for preparation of trans-resveratrol in tree peony seed oil-extracted residues using imidazolium-based ionic liquid

Chen

Zhang²,

Zhang

et al. 2016

Industrial Crops and Products

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a b s t r a c tImidazolium-based ionic liquid-based microwave-ultrasonic synergistic simultaneous extraction and hydrolysis (IMUSEH) method was developed to obtain trans-resveratrol from tree peony (Paeonia rockii (S.G. Haw & Lauener) T. Hong & J.J. Li) seed oil-extracted residues, in which the basic ionic liquid aqueous solution was used for extraction and transformation of trans-resveratrol glycosides to free transresveratrol. Through comparison, 1-butyl-3-methylimidazolium imidazolide ([C 4 C 1 im]Im) was selected as a dual solvent-catalyst, which showed an excellent solvent effect and catalytic activity. After optimization by a factorial design and response surface methodology, a higher yield of trans-resveratrol (3.06 ± 0.12 mol/g) was obtained under optimal conditions (0.5 M [C 4 C 1 im]Im, 24 mL/g liquid-solid ratio, 25 min time, and 396 W microwave irradiation power). The developed technique was compared with ionic liquid-based microwave-assisted extraction and ionic liquid-based ultrasonic-assisted extraction based on first-order kinetic model and scanning electron microscopy, which highlighted the mechanism of the microwave-ultrasonic synergistic apparatus. Method validation studies showed that the proposed method can be used to prepare trans-resveratrol. The developed method showed promise in transforming glucoside to aglycone in plant materials.

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Solubilities of pharmaceutical and bioactive compounds in trihexyl(tetradecyl)phosphonium chloride ionic liquid

Cited by 23 publications

References 38 publications

Solubility Data as a Response for a Challenge for Formulation Chemists: Imidazolium-Based Ionic Liquids and Antitubercular Antibiotic Medicines

Solubility Data as a Response for a Challenge for Formulation Chemists: Imidazolium-Based Ionic Liquids and Antitubercular Antibiotic Medicines

Advances Brought by Hydrophilic Ionic Liquids in Fields Involving Pharmaceuticals

Simultaneous synergistic microwave–ultrasonic extraction and hydrolysis for preparation of trans-resveratrol in tree peony seed oil-extracted residues using imidazolium-based ionic liquid

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