New flourinated chitin derivatives: Synthesis, characterization and cytotoxicity assessment

Abstract

New fluorinated chitin derivatives have been synthesized and characterized. Fluorination of chitin was achieved by facile homogenous reaction of chitin solution with diethyl amino sulfur trifluoride (C4H10NSF3). The degree of substitution of the C6-hydroxyl functionality of N-acetyl-glucosamine repeat unit ranged from 50 to 98%, achieved by varying the reaction time from 1 to 144 h at room temperature. The use of pentafluoropropionic anhydride, trifluoromethylbenzoyl chloride and pentafluorobenzoyl chloride gave fluoro-chitin derivatives with 40, 10 and 5% substitution, respectively. Solid-state nuclear magnetic resonance and Fourier-transform infrared spectroscopy, powder X-ray diffraction, and elemental analysis support the identity of all fluorinated chitin derivatives. The fluorinated chitin derivatives were subjected to MTT assay using human (ATCC CCL-186) and mouse (ATCC CCL-1) fibroblast cell lines. Fluorinated chitin derivatives prepared from C4H10NSF3 at 1, 6, 12, 72 and 96 h showed good cell viability of 80-100% for human fibroblast and 60-70% for mouse fibroblast. The % cell viability for the other fluorinated chitin derivatives were above 60% for both cell lines. © 2002 Elsevier Science Ltd. All rights reserved.