Semi-synthesis of hybrid ulvan-kappa-carrabiose polysaccharides and evaluation of their cytotoxic and anticoagulant effects

• Published in: Carbohydrate polymers Vol. 267; p. 118161
• Main Authors: Colodi, Franciely G., Ducatti, Diogo R.B., Noseda, Miguel D., de Carvalho, Mariana M., Winnischofer, Sheila M.B., Duarte, Maria Eugênia R.
• Format: Journal Article
• Language: English
• Published: Elsevier Ltd 01-09-2021
• Subjects: Amidation; Biocompatibility; Hybrid polysaccharide; Kappa-carrageenan; Polysaccharide modification; Ulvan; Hybrid polysaccharide; Biocompatibility; Polysaccharide modification; Ulvan; Amidation; Kappa-carrageenan
• ISSN: 0144-8617; 1879-1344
• DOI: 10.1016/j.carbpol.2021.118161

In this study we described the synthesis of a hybrid polysaccharide harboring moieties of ulvan and kappa-carrabiose. Alkylamines (1,3-diaminopropane and 1,6-diaminohexane) were selectively inserted into β-D-GlcAp and α-L-IdoAp units in the ulvan structure via an amide bond formation producing ulvan-amide derivatives F-DAP (N% = 1.77; Mw = 208 kg mol−1) and F-DAH (N% = 1.77; Mw = 202 kg mol−1), which were reacted with kappa-carrabiose via reductive amination to produce hybrid ulvan-kappa-carrabiose polysaccharides F-DAP-Kb (N% = 1.56; Mw = 206 kg mol−1) and F-DAH-Kb (N% = 1.16; Mw = 200 kg mol−1). All the ulvan derivatives were characterized by 1H and 13C NMR spectroscopy and did not show cytotoxicity against human dermal fibroblasts (HDFa) at the concentrations of 25, 100, and 500 μg mL−1, neither anticoagulant properties at the range of 10–150 μg mL−1. Therefore, the ulvan-amide derivatives and the hybrid ulvan-kappa-carrabiose polysaccharides showed good biocompatibility in vitro, presenting as worthy candidates for tailoring scaffolds for biomedical applications.
•Hybrid ulvan/carrageenan derivatives were synthesized by regioselective modification.•The ulvan derivatives were synthesized using EDC coupling and reductive amination.•The hybrid polysaccharides were characterized by FTIR and NMR spectroscopy.•Hybrid ulvan/k-carrabiose derivatives did not show cytotoxicity against HDFa cells.•Alkylamino and k-carrabiose moieties did not increase the anticoagulant property.