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Synthesis and characterization of N-(2-aminoethyl)-2-acetamidyl gellan gum with potential biomedical applications
Authors:O. Novac  G. Lisa  E. Barbu  F. Alhaique  M.I. Popa
Affiliation:1. “Gh. Asachi” Technical University, Faculty of Chemical Engineering and Environmental Protection, Physical-Chemistry Department, 73 A, Prof. Dr. D. Mangeron Street, 700050 Iasi, Romania;2. University of Portsmouth, School of Pharmacy and Biomedical Sciences, St. Michael Building, White Swan Road, Portsmouth PO1 2DT, United Kingdom;3. University of Rome “La Sapienza”, Department of Drug Chemistry and Technologies, p.le Aldo Moro 5, 00185 Rome, Italy
Abstract:N-(2-aminoethyl)-2-acetamidyl gellan gum (GCM-EDA) was prepared by carboxymethylation (via nucleophilic substitution of primary hydroxyl groups of the β-d-glucose unit of gellan gum, in the presence of alkali and chloroacetic acid) and reaction with tert-butyl N-(2-aminoethyl) carbamate (N-Boc-EDA) using 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDAC) as an activator, followed by deprotection with trifluoroacetic acid. The structural confirmation and characterization of N-(2-aminoethyl)-2-acetamidyl gellan gum was performed by spectroscopic, rheological and thermogravimetric analysis, and in vitro tests showed a lack of cytotoxicity which is indicative of the potential of this material to be used in biomedical applications.
Keywords:Gellan gum   Carboxymethylation   N-Boc deprotection   Aminated derivative   Rheology   Cytotoxicity
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