Open AccessAcyclovir as an Ionic Liquid Cation or Anion Can Improve Aqueous Solubility
Author(s) -
Julia L. Shamshina,
O. Andreea Cojocaru,
Steven P. Kelley,
Katharina Bica,
Sergey P. Wallace,
Gabriela Gurău,
Robin D. Rogers
Publication year - 2017
Publication title -
acs omega
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.779
H-Index - 40
ISSN - 2470-1343
DOI - 10.1021/acsomega.7b00554
Subject(s) - counterion , chemistry , solubility , aqueous solution , ionic liquid , cationic polymerization , inorganic chemistry , ion , ionic bonding , chloride , polymer chemistry , organic chemistry , catalysis
Six ionic liquid (IL)-forming ions (choline, tetrabutylphosphonium, tetrabutylammonium, and trimethylhexadecylammonium cations, and chloride and docusate anions) were paired with acyclovir as the counterion to form four low melting solid salts and two waxes; five of these compounds could be classified as ILs. All of the newly synthesized acyclovir ILs exhibited increased aqueous solubilities by at least 2 orders of magnitude when compared to that of neutral acyclovir. For three of the prepared compounds, the solubilities in simulated body fluids (phosphate-buffered saline, simulated gastric, and simulated intestinal fluids) were also greatly enhanced when compared to that of neutral acyclovir. Acyclovir in its anionic form was more water- or buffer-soluble than acyclovir in its cationic form, though this might be the effect of the particular ions, indicating that the solubilities can be finely tuned by proper choice of the cationic or anionic form of acyclovir and the counterion paired with it.
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