Rod-like cellulose nanocrystals (CNCs) offer unique opportunities for the design of therapeutic agents given the established biocompatibility of cellulose and historical use of cellulosic materials in the pharmaceutical industry.  Having a large specific surface area, multivalent displays of target-specific ligands can be achieved via covalent conjugation to nanocrystals. In the present study, CNCs produced from sulfuric acid hydrolysis were utilized as a substrate for the conjugation of tyrosine sulfate mimetic ligands.  To this end, CNC surface hydroxyl residues were functionalized with small molecule ligands via isothiocyanate chemistry.  To increase ligand mobility, oligo(ethylene glycol) molecular spacers were introduced first by activation of CNC surface hydroxyls in aqueous or organic media by epichlorohydrin or 1,1'-carbonyldiimidazole, respectively.  The extent of surface functionalization was determined by TGA and XPS. Chemical and topographical information were accessed via ATR-FTIR Spectroscopy and AFM. The potential applications of tyrosine sulfate mimetics are presented and discussed.

Design and synthesis of multivalent cellulose nanocrystals carrying tyrosine sulfate mimetic ligands

243rd National Meeting (2012)

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