title: Preparation of hyaluronan polyaldehyde-a precursor of biopolymer conjugates.
abstract: Native hyaluronan (HA) has been oxidized to polyaldehyde polymers with a degree of substitution (DS) of up to 50%. Two different procedures enabling the control of the degree of substitution were followed in this study. Selective oxidation of primary hydroxyl groups of N-acetyl-D-glucosamine of hyaluronan was performed either in an aqueous solution containing AcNH-TEMPO/NaBr/NaOCl or in an aprotic solvent containing Dess-Martin periodinane (DMP). It was found that a change of reaction parameters (reaction time and temperature, type of catalyst, oxidant-to-HA ratio, presence of nitrogen, buffer type, and concentration) had an influence on the degree of substitution and molecular weight. The derivatives were characterized by MS, NMR spectroscopy, and SEC-MALLS. Degradation of hyaluronic acid by the oxidant was observed and confirmed by SEC. The effect of oxidized derivatives of hyaluronan on cells was studied by means of NIH 3T3 fibroblast viability, which indicates that prepared hyaluronan polyaldehydes are biocompatible and suitable for medical applications and tissue engineering. The function of polyaldehyde as precursor for other modification was illustrated in the reaction with lysine.
authors: Biotech Contipro, 561 02 Dolní Dobrouč 401, Czech Republic. petra.sedova@contipro.com
authors: Petra
authors: P
authors: Šedová
authors: Radovan
authors: R
authors: Buffa
authors: Sofiane
authors: S
authors: Kettou
authors: Gloria
authors: G
authors: Huerta-Angeles
authors: Martina
authors: M
authors: Hermannová
authors: Veronika
authors: V
authors: Leierová
authors: Daniela
authors: D
authors: Šmejkalová
authors: Martina
authors: M
authors: Moravcová
authors: Vladimír
authors: V
authors: Velebný
mesh_terms: D000117:Acetylglucosamine / Q000737:chemistry; D000447:Aldehydes / Q000138:chemical synthesis* / Q000494:pharmacology; D000818:Animals; D001672:Biocompatible Materials / Q000138:chemical synthesis* / Q000494:pharmacology; D001704:Biopolymers / Q000737:chemistry* / Q000494:pharmacology; D001965:Bromides / Q000737:chemistry; D002384:Catalysis; D002470:Cell Survival / Q000187:drug effects; D003497:Cyclic N-Oxides / Q000737:chemistry; D006820:Hyaluronic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000494:pharmacology; D050112:Imino Pyranoses / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D008970:Molecular Weight; D041681:NIH 3T3 Cells; D009584:Nitrogen / Q000737:chemistry; D010084:Oxidation-Reduction; D017670:Sodium Compounds / Q000737:chemistry; D012973:Sodium Hypochlorite / Q000737:chemistry; D013696:Temperature
chemical_list: D000447:Aldehydes; D001672:Biocompatible Materials; D001704:Biopolymers; D001965:Bromides; D003497:Cyclic N-Oxides; D050112:Imino Pyranoses; D017670:Sodium Compounds; D006820:Hyaluronic Acid; D012973:Sodium Hypochlorite; C027938:sodium bromide; D009584:Nitrogen; D000117:Acetylglucosamine; C003959:TEMPO