The effect of aminooxy-linkers’ structure on the mechanical properties of hyaluronan-oxime hydrogels

• Published in: Express polymer letters Vol. 16; no. 3; pp. 265 - 278
• Main Authors: Sedova, Petra, Buffa, Radovan, Koci, Tereza, Kovarova, Lenka, Bednarik, Jiri, Vagnerova, Hana, Velebny, Vladimir
• Format: Journal Article
• Language: English
• Published: Budapest Budapest University of Technology and Economics, Faculty of Mechanical Engineering, Department of Polymer Engineering 01-03-2022; Budapest University of Technology
• Subjects: Aldehydes; Alkanes; Benzene; Chromatography; Crosslinking; Cyclodextrins; Cytotoxicity; Functional groups; Gelation; hyaluronan; Hyaluronic acid; Hydrocarbons; Hydrogels; Investigations; Mechanical properties; Optimization; oxyamine; polymer gels; Polymers; rheology; Rigidity; Sodium; Stiffness; Tissue engineering; Toxicity; Wound healing; France; United States > US; Czech Republic
• ISSN: 1788-618X; 1788-618X
• DOI: 10.3144/expresspolymlett.2022.21

The wide range of hydrogel applications is a result of the optimization of gelation. Herein, the various aminooxylinkers were synthesized to study the kinetics of gelation and mechanical properties of hydrogels prepared by crosslinking of aldehyde-modified N-acetylglucosamine (GlcNAc) of hyaluronan (ДНА-CHO: 4,5-anhydro-6-(GlcNAc)-oxo hyaluronan or HA-CHO: 6-(GlcNAc)-oxo hyaluronan). Structural characteristics of the linkers (length, number of functional groups and rigidity) and the polymer (effect of the -C=C- double bond) were investigated in detail and showed decreasing mechanical stiffness with increasing hydrophobic character of linker and effect of its rigidity/flexibility on imine conversion. Besides known linear bis(aminooxy)alkanes with different lengths of the chain, new multifunctional aminooxy-linkers: 1,3,5tris(aminooxymethyl)benzene and multikis(6-aminooxy-6-deoxy)-ß-cyclodextrin were prepared and shortened the gelation time. The MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) analysis showed that despite the aminooxylinkers' cytotoxicity at higher concentrations, the final oxime hydrogels are non-cytotoxic and therefore are suitable for medicinal applications.