Xylan‐Based Nanoparticles: Prodrugs for Ibuprofen Release

Abstract

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.

Towards unnatural xylan based polysaccharides: reductive amination as a tool to access highly engineered carbohydrates

“…The weight average molecular weight (M w ) determined with MALDI-TOF mass spectrometry amounts 1,980 g/mol, which is consistent with SEC measurements using a universal calibration. The mass spectrum underlying the calculation is published elsewhere (Daus and Heinze 2010).…”

Xylan, a Promising Hemicellulose for Pharmaceutical Use

“…In the drug delivery field, xylan extracted from birch wood has been used for the production of nanoparticles after structural modification by the addition of different ester moieties, namely those with furoate and pyroglutamate functions (Heinze et al, 2007). On the other hand, the esterification of xylan from beech wood via activation of the carboxylic acid with N,N"-carbonyldiimidazole has been carried out in order to produce prodrugs for ibuprofen release (Daus & Heinze, 2010).…”

Leads from Physical, Chemical, and Thermal Characterization on Cytotoxic Effects of Xylan-Based Microparticles

“…When administered by the oral route, this polysaccharide is only degradable at the ascendant and transversal colon region due to the presence of bacteria that produce and excrete xylanases into the gastrointestinal tract [5,6]. However, its use as a raw material for the production of drug delivery systems has emerged in the recent literature [7,8]. Our group has also evaluated the production of colon-targeted drug carriers as a promising application for xylan [9,10].…”