Polyethylene glycol derivatization of the non-active ion in active pharmaceutical ingredient ionic liquids enhances transdermal delivery
| Autor: | Giovanni P. Rachiero, Robin D. Rogers, Parker D. McCrary, Hatem M. Titi, Julia L. Shamshina, Max S. Mittenthal, Oleksandra Zavgorodnya |
|---|---|
| Rok vydání: | 2017 |
| Předmět: |
chemistry.chemical_classification
Salt (chemistry) 02 engineering and technology General Chemistry Polyethylene glycol Membrane transport 010402 general chemistry 021001 nanoscience & nanotechnology 01 natural sciences Catalysis 0104 chemical sciences Solvent chemistry.chemical_compound Membrane chemistry parasitic diseases Ionic liquid Polymer chemistry Materials Chemistry Organic chemistry 0210 nano-technology Sodium salicylate Triethylene glycol |
| Zdroj: | New Journal of Chemistry. 41:1499-1508 |
| ISSN: | 1369-9261 1144-0546 |
| DOI: | 10.1039/c6nj03709g |
| Popis: | We report the synthesis of four salts composed of the salicylate anion ([Sal]−) paired with tributylammonium ([HN444]+), choline ([Cho]+), 1-methylpyrrolidinium ([HMPyrr]+), and triethylene glycol monomethyl ether tributylammonium ([mPEG3N444]+) cations. Three of the synthesized salts (room temperature liquids [mPEG3N444][Sal] and [Cho][Sal], and a supercooled liquid [HN444][Sal]) belong to the category of ionic liquids (ILs), and one salt (solid [HMPyrr][Sal]) was a crystalline solid. ILs in their neat form were studied for membrane transport through a silicon membrane, and exhibited higher transport compared to a control experiment with sodium salicylate dissolved in mPEG3OH as solvent, but lower membrane transport compared to salicylic acid dissolved in mPEG3OH. The ‘PEGylated’ IL, [mPEG3N444][Sal], crossed the membrane with an ca. ∼2.5-fold faster rate than that of any of the non-PEGylated ILs. This work demonstrates not only that API–ILs can eliminate the use of a solvent vehicle during application and notably transport through a membrane as opposed to a higher melting crystalline salt, but also that the membrane transport can be further enhanced by PEGylation of the counter ions. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|