Cholinium-based ionic liquids with pharmaceutically active anions

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abstract

Novel ionic liquids (ILs) containing cholinium as a benign cation combined with anions based on five active pharmaceutical ingredients (APIs), namely, nalidixic acid, niflumic acid, 4-amino-salicylic acid, pyrazinoic acid and picolinic acid, were prepared via a simple and sustainable two-step anion exchange reaction. The solubility of the prepared pharmaceutically active ILs (API-ILs) in both water and simulated biological fluids at 25 degrees C and 37 degrees C, as well as the solubility of the parent APIs, were measured. Further, in vitro cytotoxicity levels for both cholinium-based API-ILs and parent APIs were established using two different human cells lines, namely Caco-2 colon carcinoma cells and HepG2 hepatocellular carcinoma cells. Herein, the dual nature of ILs is exploited by combining the cheap, available and essential nutrient cholinium cation with pharmaceutically active anions, upgrading the chemical, physical and biopharmaceutical properties, particularly melting point, aqueous solubility and the potential to penetrate cell membranes of the parent APIs, without impair their cytotoxicity response which prompt opportunities for creating further advances in pharmaceutical challenges.

keywords

NIFLUMIC ACID; DISSOLUTION MECHANISM; NMR-SPECTROSCOPY; NALIDIXIC-ACID; CELL-LINE; SOLUBILITY; MIXTURES; DRUGS; PHARMACOKINETICS; LIPOPHILICITY

subject category

Chemistry

authors

Araujo, JMM; Florindo, C; Pereiro, AB; Vieira, NSM; Matias, AA; Duarte, CMM; Rebelo, LPN; Marrucho, IM

our authors

foto Isabel Maria Delgado Jana Marrucho Ferreira

Isabel Maria Delgado Jana Marrucho Ferreira

Full professor

Groups

Projects

The best of two worlds: Ionic liquids as Active Pharmaceutical Ingredients (PTDC/EQU-EPR/104554/2008)

Development of New Oxygen Therapeutics using Fluorinated Ionic Liquids (PTDC/EQU-FTT/118800/2010)

acknowledgements

The financial support from FCT/MEC (Portugal), through grants SFRH/BPD/65981/2009 (J. M. M. Araujo) and SFRH/BPD/84433/2012 (A. B. Pereiro) and a contract under Investigador FCT 2012 (I. M. Marrucho), and through projects PTDC/EQU-EPR/104554/2008, PTDC/EQU-FTT/118800/2010 and PEst-OE/EQB/LA0004/2013 is gratefully acknowledged. The NMR spectrometers are part of The National NMR Facility, supported by Fundacao para a Ciencia e a Tecnologia (RECI/BBB-BQB/0230/2012).

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Publication Details

type
Journal Article
year
2014
journal
RSC ADVANCES
volume
4
publisher
ROYAL SOC CHEMISTRY
issn
2046-2069
issue
53
digital object identifier
10.1039/c3ra47615d
web of science article identifier
WOS:000339012400064

Journal Metrics (JCR 2019)

Journal Impact Factor
3.119
Journal Impact Factor (5 yrs)
3.098
category normalized journal percentile
59.04

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