Xylan-based nanoparticles: prodrugs for ibuprofen release.
Esterification of xylan with ibuprofen via activiation of the carboxylic acid with N,N'-carbonyldiimidazole (CDI) yields products of high drug loadings. Subsequent sulfation of xylan ibuprofen esters using the gentle agent SO(3)/DMF was successfully carried out in order to modify hydrophobicity of the xylan esters. The structure of the novel xylan esters was evaluated by means of NMR spectroscopy. The resulting xylan derivatives self assemble into spherical nanoparticles with mean diameters ranging from 162 to 472 nm. Preliminary stability measurements indicate that hydrolytic stability decreases with increase in degree of substitution of sulfate groups. Thus, a new concept toward improved drug delivery from polysaccharide-based nanoparticles can be established here.
Daus
Stephan
S
Center of Excellence for Polysaccharide Research, Friedrich Schiller University of Jena, Humboldtstrasse 10, D-07743 Jena, Germany.
Heinze
Thomas
T
D000215:Acylation / Q000187:drug effects; D016503:Drug Delivery Systems; D004355:Drug Stability; D004951:Esterification / Q000187:drug effects; D006868:Hydrolysis / Q000187:drug effects; D007052:Ibuprofen / Q000737:chemistry / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy; D053758:Nanoparticles / Q000737:chemistry* / Q000648:ultrastructure; D054118:Nanospheres / Q000648:ultrastructure; D010316:Particle Size; D011355:Prodrugs / Q000494:pharmacology*; D013050:Spectrometry, Fluorescence; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; D013455:Sulfur / Q000378:metabolism; D014990:Xylans / Q000737:chemistry*
D011355:Prodrugs; D014990:Xylans; D013455:Sulfur; D007052:Ibuprofen