Design of l‑Lysine-Based Organogelators and Their Applications in Drug Release Processes

• Published in: ACS omega Vol. 4; no. 7; pp. 12342 - 12356
• Main Authors: Kaplan, Seref, Colak, Mehmet, Hosgoren, Halil, Pirinccioglu, Necmettin
• Format: Journal Article
• Language: English
• Published: United States American Chemical Society 31-07-2019
• ISSN: 2470-1343; 2470-1343
• DOI: 10.1021/acsomega.9b01086

This work reports on the synthesis of three new l-lysine-based organogelators bis­(N2-alkanoyl-N6-l-lysyl ethylester)­oxalylamides, where alkanoyls are lauroyl, myristoyl, and palmitoyl. The gels of these gelators were prepared with high yields in eco-friendly solvents commonly used in cosmetics such as ethyl and isopropyl esters of lauric and myristic acids, liquid paraffin, 1-decanol, and 1,2-propanediol. Fourier transform infrared measurements revealed the involvement of intermolecular hydrogen bonds in the gelation. Scanning electron microscopy images of xerogels indicated different morphologic patterns with regard to the alkanoyl chain length and the solvent employed in their preparation. The gel formation was supported by rheological measurements. Three gels prepared in liquid paraffin were loaded with naproxen (Npx) with a quite high loading capacity (up to 166.6% as percentage of gelator) without gel disruption. The release of Npx from the gel matrix into the buffered solution at physiologic pH was evaluated using UV–vis spectroscopy. The results revealed that the release rate of Npx from the organogels significantly retarded with increasing organogelator concentration, whereas it enhanced with increasing Npx concentration. The rate was also found to be pH-dependent; the lower the pH, the lower the rate. Furthermore, molecular dynamic calculations performed on the octamer of myristoyl-bearing gelator (N 2 M/N 6 Lys) in 1,2-propanediol provided useful information regarding the structural properties of the gels, which may be of interest to interpret the structure of the gel matrix. Altogether, this work provided valuable outcomes, which may be relevant to the pharmaceutical industry. It may be suggested that l-lysine-based gels have potentials in the delivery of nonsteroidal anti-inflammatory drug molecules. Besides, the release of the drug can be fine-tuned by the correct choice of gelator–solvent combination.