Polymer – Ionic liquid – Pharmaceutical conjugates as drug delivery systems

Mohammed Halayqa , Maciej Zawadzki , Urszula Domańska-Żelazna , Andrzej Plichta


Synthesis of a novel drug delivery system based on active pharmaceutical ingredient (API), ammonium ionic liquid (IL) and grafted–Poly(l-lactide) (API-IL-LA) is presented. Sparingly water-soluble mefenamic acid (MEF) was used as a model drug for the investigation of drug loading efficiency and drug release performance. The synthesis of four ammonium ILs: 2-hydroxyethyl triethyl ammonium bromide, N21-Br, 2-hydroxyethyl tributyl ammonium bromide, N41-Br, di(2-hydroxyethyl)dibutyl ammonium bromide, N42-Br and tri(2-hydroxyethyl)butyl ammonium bromide, N43-Br is described. The synthesized bromide salts were used as an initiator for the ring opening polymerization (ROP) of lactide (LA) with triflic acid as a catalyst. The drug delivery systems of Mefenamate-ammonium-based IL-Polylactide (MEF-IL-LA) were synthesized by metathesis reaction of polylactide ammonium ionic liquid (IL-LA) with silver mefenamate. The (API-IL-LA) compounds, obtained at T = 333 K with different LA:IL ratios 20:1, 40:1 and 80:1 were used for the formulation of nanoparticles (NPs) by an emulsion-solvent evaporation technique. The obtained NPs have spherical shapes and controlled sizes of 279.1 ± 3.6 nm to 453.3 ± 4.9 nm with maximum encapsulation efficiency up to 92.0 ± 2.7%. Solid NPs were evaluated for in vitro release in phosphate–buffered saline (pH = 7.4) by using dialysis bags at temperature T = 310 K. All NPs have shown controlled and sustained release up to 120 h and 168 h, dependent on alkyl chain substituent and the number of hydroxyethyl groups in the molecule, respectively. The data acquired from drug release profiles were correlated by the pseudo-second-order kinetics model. It was observed that formation of ionic pairs between API and polymer matrix decreased API release rate.
Author Mohammed Halayqa (FC / DPC)
Mohammed Halayqa,,
- Department Of Physical Chemistry
, Maciej Zawadzki (FC / DPC)
Maciej Zawadzki,,
- Department Of Physical Chemistry
, Urszula Domańska-Żelazna - [Instytu Chemii Przemysłowej im. prof. Ignacego Mościckiego]
Urszula Domańska-Żelazna,,
- Instytu Chemii Przemysłowej im. prof. Ignacego Mościckiego
, Andrzej Plichta (FC / CPCT)
Andrzej Plichta,,
- Chair Of Polymer Chemistry And Technology
Journal seriesJournal of Molecular Structure, ISSN 0022-2860
Issue year2019
Publication size in sheets0.55
Keywords in EnglishSynthesis of API-IL-LA compoundsNanoparticlesPhysico-chemical properties of NPsDrug release-kinetic model
ASJC Classification1602 Analytical Chemistry; 1604 Inorganic Chemistry; 1605 Organic Chemistry; 1607 Spectroscopy
URL https://www.sciencedirect.com/science/article/pii/S0022286018314443?via%3Dihub
Languageen angielski
1-s2.0-S0022286018314443-main.pdf 2.72 MB
Score (nominal)70
Score sourcejournalList
ScoreMinisterial score = 70.0, 02-07-2020, ArticleFromJournal
Publication indicators Scopus Citations = 5; WoS Citations = 3; Scopus SNIP (Source Normalised Impact per Paper): 2018 = 0.807; WoS Impact Factor: 2018 = 2.12 (2) - 2018=1.861 (5)
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