Effects of different head groups and functionalised side chains on the aquatic toxicity of ionic liquids

Stolte, Stefan; Arning, Jürgen; Bottin‐Weber, Ulrike; Müller, Anja; Pitner, William R.; Welz‐Biermann, Urs; Jastorff, Bernd; Ranke, Johannes

doi:10.1039/b711119c

Cited by 438 publications

(383 citation statements)

References 63 publications

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“…Compared with traditional organic solvents such as ethanol, ILs can be formulated to be less toxic to cells (44). These findings address a major issue associated with solventinduced skin irritation typical with many skin formulations.…”

Section: Discussionmentioning

confidence: 82%

Ionic liquids as a class of materials for transdermal delivery and pathogen neutralization

Zakrewsky

Lovejoy

Kern

et al. 2014

Proc. Natl. Acad. Sci. U.S.A.

265

270

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Biofilm-protected microbial infections in skin are a serious health risk that remains to be adequately addressed. The lack of progress in developing effective treatment strategies is largely due to the transport barriers posed by the stratum corneum of the skin and the biofilm. In this work, we report on the use of Ionic Liquids (ILs) for biofilm disruption and enhanced antibiotic delivery across skin layers. We outline the syntheses of ILs, analysis of relevant physicochemical properties, and subsequent neutralization effects on two biofilm-forming pathogens: Pseudomonas aeruginosa and Salmonella enterica. Further, the ILs were also examined for cytotoxicity, skin irritation, delivery of antibiotics through the skin, and treatment of biofilms in a wound model. Of the materials examined, choline-geranate emerged as a multipurpose IL with excellent antimicrobial activity, minimal toxicity to epithelial cells as well as skin, and effective permeation enhancement for drug delivery. Specifically, choline-geranate was comparable with, or more effective than, bleach treatment against established biofilms of S. enterica and P. aeruginosa, respectively. In addition, cholinegeranate increased delivery of cefadroxil, an antibiotic, by >16-fold into the deep tissue layers of the skin without inducing skin irritation. The in vivo efficacy of choline-geranate was validated using a biofilm-infected wound model (>95% bacterial death after 2-h treatment). This work establishes the use of ILs for simultaneous enhancement of topical drug delivery and antibiotic activity.antibacterial | antimicrobial agents | antibiotic resistance | ion-pairing | formulation

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Section: Discussionmentioning

confidence: 82%

Ionic liquids as a class of materials for transdermal delivery and pathogen neutralization

Zakrewsky

Lovejoy

Kern

et al. 2014

Proc. Natl. Acad. Sci. U.S.A.

265

270

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“…Although the negligible volatility of ILs is one appealing point in the use of ILs in place of volatile organic solvents, the finite solubility of ILs in water has raised concern in wastewater treatments and other circumstances. [169][170][171][172][173][174][175][176][177][178][179][180][181][182][183][184][185][186][187] Since ILs are salts having certain solubility in water, the interface between an IL and water is inevitably electrified. There are a number of systems in which the phase-boundary potential across the IL|W interface plays a crucial role in determining the physicochemical characteristics of the systems.…”

Section: Introductionmentioning

confidence: 99%

Mutual Solubility of Hydrophobic Ionic Liquids and Water in Liquid-Liquid Two-phase Systems for Analytical Chemistry

Kakiuchi

2008

ANAL. SCI.

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Liquid-liquid two-phase systems formed by a hydrophobic ionic liquid and water find several useful ways of application in analytical chemistry. One of the most important properties of such two-phase systems is the mutual solubility of the IL and water. Recent advancements on this subject have been reviewed. The solubility of ionic liquids in water is related to the standard Gibbs energies of the transfer of ions constituting the ionic liquid from the ionic liquid phase to water. Although this single ionic property cannot be measured thermodynamically and also varies from one ionic liquid to another, the standard Gibbs energy of the ion transfer from a polar aprotic solvent, such as nitrobenzene and 1,2-dichloroethane, to water is a convenient measure for it. The solubility of an ionic liquid in water and the electrochemical properties at the interface between the two phases are intimately related with each other.

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“…[23,24] Furthermore, compared to conventional chemical penetration enhancers such as ethanol, ILs demonstrated lesser toxicity to cells thereby mitigating the issue of skin irritation that is characteristic of many chemical enhancers. [23,25] DES's are a mixture of compounds that collectively have a lower freezing temperature than individual components while ILs are salts consisting of an organic cation and organic/inorganic anion that are stable and in a liquid form at room temperature.…”

mentioning

confidence: 99%

Transdermal Protein Delivery Using Choline and Geranate (CAGE) Deep Eutectic Solvent

Banerjee

Ibsen

Iwao

et al. 2017

Adv Healthcare Materials

163

155

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Transdermal delivery of peptides and other biological macromolecules is limited due to skin's inherent low permeability. Here, the authors report the use of a deep eutectic solvent, choline and geranate (CAGE), to enhance topical delivery of proteins such as bovine serum albumin (BSA, molecular weight: ≈66 kDa), ovalbumin (OVA, molecular weight: ≈45 kDa) and insulin (INS, molecular weight: 5.8 kDa). CAGE enhances permeation of BSA, OVA, and insulin into porcine skin ex vivo, penetrating deep into the epidermis and dermis. Studies using tritium-labeled BSA and fluorescein isothiocyanate labeled insulin show significantly enhanced delivery of proteins into and across porcine skin, penetrating the skin in a time-dependent manner. Fourier transform IR spectra of porcine stratum corneum (SC) samples before and after incubation in CAGE show a reduction in peak area attributed to SC lipid content, suggesting lipid extraction from the SC. Circular dichroism confirms that CAGE does not affect insulin's secondary conformation. In vivo studies in rats show that topical application of 10 U insulin dispersed in CAGE (25 U kg −1 insulin dose) leads to a highly significant 40% drop in blood glucose levels in 4 h that is relatively sustained for 12 h. Taken together, these studies demonstrate that CAGE is a promising vehicle for transdermal delivery of therapeutic proteins; specifically, as a noninvasive delivery alternative to injectable insulin for the treatment of diabetes.

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Effects of different head groups and functionalised side chains on the aquatic toxicity of ionic liquids

Cited by 438 publications

References 63 publications

Ionic liquids as a class of materials for transdermal delivery and pathogen neutralization

Ionic liquids as a class of materials for transdermal delivery and pathogen neutralization

Mutual Solubility of Hydrophobic Ionic Liquids and Water in Liquid-Liquid Two-phase Systems for Analytical Chemistry

Transdermal Protein Delivery Using Choline and Geranate (CAGE) Deep Eutectic Solvent

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