title: Synthesis and characterization of a biocompatible chitosan-based hydrogel cross-linked via 'click' chemistry for controlled drug release.
abstract: A chemically cross-linked chitosan-based hydrogel was successfully synthesized through Diels-Alder (DA) reaction and characterized. The final product was obtained after different steps; on the one hand, furan-modified chitosan (Cs-Fu) was synthesized by the reaction of furfural with the free amino groups of chitosan. On the other hand, highlighting the novelty of the present research, maleimide-functionalized chitosan (Cs-AMI) was prepared by the reaction of a maleimide-modified aminoacid with the amino groups of chitosan through amide coupling. The two complementary chitosan derivatives were cross-linked to the final hydrogel network. Both modification reactions were confirmed by FTIR and1H NMR, obtaining a degree of substitution (DS) of 31% and 26% for Cs-Fu and Cs-AMI, respectively. The as-designed hydrogel was analyzed in terms of microstructure, swelling capacity and rheological behaviour. The hydrogel showed pH-sensitivity, biocompatibility and inhibitory bacterial activity, promising features for biomedical applications, particularly for targeted-drug delivery.
authors.affiliation: `Materials+Technologies´ Group, Department of Chemical and Environmental Engineering, Engineering College of Gipuzkoa, University of the Basque Country, Plaza Europa 1, 20018 Donostia-San Sebastián, Spain. Electronic address: olatz.guaresti@ehu.eus.
authors.forename: O
authors.initials: O
authors.lastname: Guaresti
authors.affiliation: `Materials+Technologies´ Group, Department of Chemical and Environmental Engineering, Engineering College of Gipuzkoa, University of the Basque Country, Plaza Europa 1, 20018 Donostia-San Sebastián, Spain. Electronic address: garciaastrain@unistra.fr.
authors.forename: C
authors.initials: C
authors.lastname: García-Astrain
authors.affiliation: Department of Cell Biology and Histology, Faculty of Medicine and Dentistry, University of the Basque Country, Barrio Sarriena s/n, 48940 Leioa, Spain. Electronic address: teodoro.palomares@ehu.eus.
authors.forename: T
authors.initials: T
authors.lastname: Palomares
authors.affiliation: Department of Cell Biology and Histology, Faculty of Medicine and Dentistry, University of the Basque Country, Barrio Sarriena s/n, 48940 Leioa, Spain. Electronic address: ana.alonsovarona@ehu.eus.
authors.forename: A
authors.initials: A
authors.lastname: Alonso-Varona
authors.affiliation: `Materials+Technologies´ Group, Department of Chemical and Environmental Engineering, Engineering College of Gipuzkoa, University of the Basque Country, Plaza Europa 1, 20018 Donostia-San Sebastián, Spain. Electronic address: arantxa.eceiza@ehu.eus.
authors.forename: A
authors.initials: A
authors.lastname: Eceiza
authors.affiliation: `Materials+Technologies´ Group, Department of Chemical and Environmental Engineering, Engineering College of Gipuzkoa, University of the Basque Country, Plaza Europa 1, 20018 Donostia-San Sebastián, Spain. Electronic address: nagore.gabilondo@ehu.eus.
authors.forename: N
authors.initials: N
authors.lastname: Gabilondo
mesh_terms: D000818:Animals; D001672:Biocompatible Materials / Q000138:chemical synthesis / Q000737:chemistry* / Q000633:toxicity; D002460:Cell Line; D002470:Cell Survival / Q000187:drug effects; D060326:Chemistry Techniques, Synthetic; D048271:Chitosan / Q000737:chemistry*; D002701:Chloramphenicol / Q000737:chemistry / Q000494:pharmacology; D057930:Click Chemistry; D003692:Delayed-Action Preparations; D004337:Drug Carriers / Q000138:chemical synthesis / Q000737:chemistry* / Q000633:toxicity; D004926:Escherichia coli / Q000187:drug effects; D005663:Furans / Q000737:chemistry; D020100:Hydrogels / Q000138:chemical synthesis / Q000737:chemistry* / Q000633:toxicity; D008301:Maleimides / Q000737:chemistry; D051379:Mice; D012212:Rheology; D013211:Staphylococcus aureus / Q000187:drug effects
chemical_list: D001672:Biocompatible Materials; D003692:Delayed-Action Preparations; D004337:Drug Carriers; D005663:Furans; D020100:Hydrogels; D008301:Maleimides; C043592:maleimide; D002701:Chloramphenicol; D048271:Chitosan; C039281:furan
keywords: Chitosan derivatives; Diels–Alder cross–linking reaction; Drug–delivery system