TY - JOUR
T1 - Cholinium-based ionic liquids with pharmaceutically active anions
AU - Araújo, João M M
AU - Florindo, Catarina
AU - Pereiro, Ana B.
AU - Vieira, Nicole S M
AU - Matias, Ana A.
AU - Duarte, Catarina M M
AU - Rebelo, Luís P N
AU - Marrucho Ferreira, Isabel Maria
N1 - WOS:000339012400064
PY - 2014
Y1 - 2014
N2 - 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 °C and 37°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. This journal is
AB - 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 °C and 37°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. This journal is
UR - http://www.scopus.com/inward/record.url?scp=84903840641&partnerID=8YFLogxK
U2 - 10.1039/c3ra47615d
DO - 10.1039/c3ra47615d
M3 - Article
AN - SCOPUS:84903840641
SN - 2046-2069
VL - 4
SP - 28126
EP - 28132
JO - RSC Advances
JF - RSC Advances
IS - 53
ER -