Protic pharmaceuticalionic liquids and solids: Aspects of protonics

Stoimenovski, Jelena; Dean, Pamela; Izgorodina, Ekaterina I.; MacFarlane, Douglas R.

doi:10.1039/c1fd00071c

Cited by 136 publications

(118 citation statements)

References 38 publications

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“…1 and Table 2, it can be affirmed that the proposed methodology, based on IL platform, is efficient concerning the tailoring of l-ampicillin water solubility. These results demonstrate the ease of water solubility manipulation, an important factor in drug delivery approaches (Stoimenovski et al, 2012).…”

Section: Water Solubility and Octanol-water Partition Coefficientmentioning

confidence: 72%

Evaluation of solubility and partition properties of ampicillin-based ionic liquids

Florindo

Araújo

Alves

et al. 2013

International Journal of Pharmaceutics

107

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a b s t r a c tIn order to overcome the problems associated with low water solubility, and consequently low bioavailability of active pharmaceutical ingredients (APIs), herein we explore a modular ionic liquid synthetic strategy for improved APIs. Ionic liquids containing l-ampicillin as active pharmaceutical ingredient anion were prepared using the methodology developed in our previous work, using organic cations selected from substituted ammonium, phosphonium, pyridinium and methylimidazolium salts, with the intent of enhancing the solubility and bioavailability of l-ampicillin forms. In order to evaluate important properties of the synthesized API-ILs, the water solubility at 25 • C and 37 • C (body temperature) as well as octanol-water partition coefficients (K ow 's) and HDPC micelles partition at 25 • C were measured. Critical micelle concentrations (CMC's) in water at 25 • C and 37 • C of the pharmaceutical ionic liquids bearing cations with surfactant properties were also determined from ionic conductivity measurements.

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Section: Water Solubility and Octanol-water Partition Coefficientmentioning

confidence: 72%

Evaluation of solubility and partition properties of ampicillin-based ionic liquids

Florindo

Araújo

Alves

et al. 2013

International Journal of Pharmaceutics

107

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“…Finally, the effective charge screening within ion pairs has been shown to facilitate the penetration of model membranes by protic ILs, thus, possibly being of interest for pharmacological applications. [105,106] …”

Section: Resultsmentioning

confidence: 98%

Imidazolium Salt Ion Pairs in Solution

Stassen

Ludwig

Wulf

et al. 2015

Chemistry A European J

169

151

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The formation, stabilisation and reactivity of contact ion pairs of non-protic imidazolium ionic liquids (ILs) in solution are conceptualized in light of selected experimental evidence as well theoretical calculations reported mainly in the last ten years. Electric conductivity, NMR, ESI-MS and IR data as well as theoretical calculations support not only the formation of contact ion pairs in solution, but also the presence of larger ionic and neutral aggregates even when dissolved in solvents with relatively high dielectric constants, such as acetonitrile and DMSO. The presence of larger imidazolium supramolecular aggregates is favoured at higher salt concentrations in solvents of low dielectric constant for ILs that contain shorter N-alkyl side chains associated with anions of low coordination ability. The stability and reactivity of neutral contact species are also dependent on the nature of the anion, imidazolium substituents, and are more abundant in ILs containing strong coordinating anions, in particular those that can form charge transfer complexes with the imidazolium cation. Finally, some ILs display reactivities as contact ion pairs rather than solvent-separated ions.

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“…Of great research and practical importance are the so-called third generation ILs, which are also known as the biologically active generation [1][2][3][4][5][6][7][8][9][10]. However, among these ILs, there are no immunoactive ones, which makes for promising materials in drug design.…”

Section: Introductionmentioning

confidence: 99%

Immunoactive ionic liquids based on 2-hydroxyethylamines and 1-R-indol-3-ylsulfanylacetic acids. Crystal and molecular structure of immunodepressant tris-(2-hydroxyethyl)ammonium indol-3-ylsulfanylacetate

et al. 2014

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Abstract:Immunoactive ionic liquids (2-hydroxyethyl) ammonium 1-R-indol-3-ylsulfanyl-acetates HNwere synthesized by the reaction of (2-hydroxyethyl)amines with indol-3-ylsulfanylaceticor 1-benzylindol-3-ylsulfanylacetic acid. 1: R 1 = R 2 = CH 2 CH 2 OH, R 3 = H; 2: R 1 = СН 3 ,R 2 =CH 2 CH 2 OH, R 3 = H; 3: R 1 = R 2 = CH 3 , R 3 = H; 4: R 1 = R 2 = CH 2 CH 2 OH, R 3 = СH 2 С 6 Н 5 ; 5: R 1 = СН 3 ; R 2 = CH 2 CH 2 OH; R 3 = СH 2 С 6 Н 5 . The structure of each compound was elucidated by IR, NMR 1 H, 13 С, and 15 N techniques and their composition was confirmed by elemental analysis. The crystal structure of tris-(2-hydroxyethyl) ammonium indol-3-ylsulfanylacetate was investigated by X-ray diffraction analysis. Immunoactive properties of the title compounds were screened.

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Protic pharmaceuticalionic liquids and solids: Aspects of protonics

Cited by 136 publications

References 38 publications

Evaluation of solubility and partition properties of ampicillin-based ionic liquids

Evaluation of solubility and partition properties of ampicillin-based ionic liquids

Imidazolium Salt Ion Pairs in Solution

Immunoactive ionic liquids based on 2-hydroxyethylamines and 1-R-indol-3-ylsulfanylacetic acids. Crystal and molecular structure of immunodepressant tris-(2-hydroxyethyl)ammonium indol-3-ylsulfanylacetate

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