Sulfated chitosan as tear substitute with no antimicrobial activity

Chitosan of high molar mass and with 82% deacetylation was sulfated using two procedures and characterized. In the first method sample chitosan-S1 was produced using chlorosulfonic acid as the sulfating agent and N,N-dimethylformamide as the medium, and in the second method (chitosan-S2) formic acid was also used. The degrees of sulfation were 0.87 (chitosan-S1) and 0.67 (chitosan-S2). FTIR spectra showed bands at 1230, 800 and 580 cm−1, attributed to sulfation. Moisture content followed the order: chitosan-S-0.87 > chitosan-S-0.67 > chitosan. Chain depolymerization was verified by GPC. Aqueous solutions showed pseudoplastic behavior and the viscosity at a concentration of 0.3% (w/v) was higher than that of healthy human tears (close to 3 mPa s at shear rate 130 s−1). Substitutions in the C2NH and in C6OH groups were verified by NMR. Antimicrobial activity against Staphylococcus aureus and Pseudomonas aeruginosa was not observed. Considering that chitosan-S-0.67 had a higher solubility, less chain depolymerization, higher yield and better thermal stability in comparison with chitosan-S-0.87, the derivative with DS 0.67 offered the greatest potential for use in formulations of tear substitutes.