Cholinium-based ionic liquids with pharmaceutically active anions
authors Araujo, JMM; Florindo, C; Pereiro, AB; Vieira, NSM; Matias, AA; Duarte, CMM; Rebelo, LPN; Marrucho, IM
nationality International
journal RSC ADVANCES
keywords NIFLUMIC ACID; DISSOLUTION MECHANISM; NMR-SPECTROSCOPY; NALIDIXIC-ACID; CELL-LINE; SOLUBILITY; MIXTURES; DRUGS; PHARMACOKINETICS; LIPOPHILICITY
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.
publisher ROYAL SOC CHEMISTRY
issn 2046-2069
year published 2014
volume 4
issue 53
beginning page 28126
ending page 28132
digital object identifier (doi) 10.1039/c3ra47615d
web of science category Chemistry, Multidisciplinary
subject category Chemistry
unique article identifier WOS:000339012400064
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