Heteroassembly Ability of Dicationic Ionic Liquids and Neutral Active Pharmaceutical Ingredients

Frizzo, Clarissa P.; Bender, Caroline R.; Salbego, Paulo R. S.; Farias, Carla A. A.; Villetti, Marcos A.; Martins, Marcos A. P.

doi:10.1021/acsomega.7b02097

Cited by 16 publications

(5 citation statements)

References 50 publications

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“…This fact may be associated with the more lipophilic nature of ILs with longer chains, or because smaller chains can be eliminated more easily by the excretory system [ 36 ]. The toxic effects of the [C 8 (MIM) 2 ][2X] DILs (in which X = Br, BF 4 , NO 3 , SCN, and Cl) on the survival of C. elegans was previously reported, with the worms’ survival rate above 90%, thus indicating no significant toxicity for these ILs at 0.01–10 mg·L −1 [ 37 ]. Therefore, considering these results and the ones presented herein, it can be seen that the toxicity of DILs against C. elegans was lower than that of monocationic IL, which may be associated with the additional cationic moiety.…”

Section: Resultsmentioning

confidence: 99%

Antimicrobial and Toxicity Evaluation of Imidazolium-Based Dicationic Ionic Liquids with Dicarboxylate Anions

et al. 2021

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Imidazolium-based dicationic ILs (DILs) presenting antimicrobial activity and relatively low toxicity are highly desirable and are envisioned for use in live tissue to prevent bacterial or fungal infections. In this context, we present here DILs with dicarboxylate anions [Cn(MIM)2[Cn(MIM)2][CO2-(CH2)mCO2], in which n = 4, 6, 8, and 10, and m = 0, 1, 2, 3, 4, and 5. The results showed that DILs with an alkyl chain spacer of ten carbons were active against yeasts and the bacterial strains tested. However, most of the DILs were cytotoxic and toxic at 1 mM. By contrast, DILs with alkyl chains possessing less than ten carbons were active against some specific Candidas and bacteria (mainly S. aureus), and they showed moderate cytotoxicity. The best activity against Gram-positive bacteria was observed for [C4(MIM)2][Pim] toward MRSA. For the DILs described herein, their level of toxicity against C. elegans was lower than that of most of the mono- and dicationic IL analogs with other anions. Our results showed that the presence of carboxylate anions reduces the toxicity of DILs compared to DILs containing halide anions, which is particularly significant to the means of designing biologically active compounds in antimicrobial formulations.

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Section: Resultsmentioning

confidence: 99%

Antimicrobial and Toxicity Evaluation of Imidazolium-Based Dicationic Ionic Liquids with Dicarboxylate Anions

et al. 2021

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“…Frizzo et al used isothermal titration calorimetry and other experiments to study the ability of hybrid assembly between cationic ILs in the presence or absence of neutral APIs with different functional groups . The results showed that API-IL binding occurred at extremely low IL concentration.…”

Section: Api-il For Enhancing Drug Deliverymentioning

confidence: 99%

Ionic Liquids for Enhanced Drug Delivery: Recent Progress and Prevailing Challenges

et al. 2022

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Ionic liquids (ILs) are a class of nonmolecular compounds composed only of ions. Compared with traditional organic solvents, ILs have the advantages of wide chemical space, diverse and flexible structures, negligible vapor pressure, and high thermal stability, which make them widely used in many fields of modern science, such as chemical synthesis and catalytic decomposition, electrochemistry, biomass conversion, and biotransformation biotechnology. Because of their special characteristics, ILs have been favored in the pharmaceutical field recently, especially for the development of efficient drug delivery systems. So far, ILs have been successfully designed to promote the dissolution of poorly soluble drugs and the destruction of physiological barriers, such as the tight junction between the stratum corneum and the intestinal epithelium. In addition, ILs can also be combined with other drug strategies to stabilize the structure of small molecules. This Review mainly introduces the application of ILs in drug delivery, emphasizes the potential mechanism of ILs, and presents the key research directions of ILs in the future.

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“…To obtain further information on the interactions between the emulsion components, 1 H NMR spectra were also acquired for pristine ILs and in the presence of increased concentrations of MCT [29,30]. Spectra in the presence of fluconazole were not obtained because of the low solubility of this drug in water [31].…”

Section: Intermolecular Interactions Between the Emulsion Componentsmentioning

confidence: 99%

Antifungal Activity and Stability of Fluconazole Emulsion Containing Ionic Liquids Explained by Intermolecular Interactions

et al. 2022

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This research reports accelerated stability experiments, the evaluation of intermolecular interactions, and antifungal assays for fluconazole emulsions prepared using ultrasound (US) and magnetic stirring (MS) in the presence of ionic liquids derived from 1,n-(3-methylimidazolium-1-yl)alkane bromide ([CnMIM]Br; n = 12 or 16). The goals of the investigation are to quantify the stability, identify the forces that drive the formation and stability, and determine the antifungal activity of fluconazole-containing emulsions, and corroborate the data from our previous results that indicated that the emulsion based on [C16MIM]Br seemed to be more stable. In this study, accelerated stability experiments evidenced a considerable stability for the [C16MIM]Br emulsions at two temperatures (25 and 37 °C)—the instability index increased in the following order: US40% < US20% < MS. The 1H NMR data showed that the ILs interacts differently with medium-chain triglycerides (MCT). Two distinct interaction mechanisms were also observed for [C12MIM]Br and [C16MIM]Br with fluconazole, in which the latter formed more compact mixed aggregates than the former. The result was corroborated by diffusion data, which showed that ILs suffered a decrease in diffusion in the presence of fluconazole. The antifungal assay showed that emulsions containing ILs displayed superior activity compared with fluconazole alone. The emulsions also showed potent activity in inhibiting a resistant species (C. glabrata—CG34) to FLZ. All emulsions showed weak irritant potential in HET-CAM assay.

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Heteroassembly Ability of Dicationic Ionic Liquids and Neutral Active Pharmaceutical Ingredients

Cited by 16 publications

References 50 publications

Antimicrobial and Toxicity Evaluation of Imidazolium-Based Dicationic Ionic Liquids with Dicarboxylate Anions

Antimicrobial and Toxicity Evaluation of Imidazolium-Based Dicationic Ionic Liquids with Dicarboxylate Anions

Ionic Liquids for Enhanced Drug Delivery: Recent Progress and Prevailing Challenges

Antifungal Activity and Stability of Fluconazole Emulsion Containing Ionic Liquids Explained by Intermolecular Interactions

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