title: Enhancing hyaluronan pseudoplasticity via 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride-mediated conjugation with short alkyl moieties.
abstract: Hyaluronan (HA) is widely used in the clinical practice and in biomedical research. Through chemical modification, HA shear-thinning properties, essential for injectability and additive manufacturing, can be optimized. In this study, we employed 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMTMM) for grafting propylamine and butylamine to HA. A parametric study was performed to identify the optimal reaction conditions. Results showed that DMTMM amidation gives reproducible and accurate control over a range of degrees of substitution (DS) from 1% to 50% and proved reliable to tune viscoelasticity. At DS=3.0% for HA-propylamine and 3.7% for HA-butylamine a maximum for storage modulus and pseudoplasticity was found, whereas above or below this DS, rheological features go back to baseline values of pristine HA. Due to their singular rheological profiles, these derivatives are valuable biomaterials candidates for preparing bioinks and hydrogels for drug delivery and regenerative medicine.
authors.affiliation: AO Research Institute Davos, Davos Platz, Switzerland; Department of Biomaterials Science and Technology, University of Twente, Enschede, The Netherlands. Electronic address: dalila.petta@aofoundation.org.
authors.forename: Dalila
authors.initials: D
authors.lastname: Petta
authors.affiliation: AO Research Institute Davos, Davos Platz, Switzerland.
authors.forename: David
authors.initials: D
authors.lastname: Eglin
authors.affiliation: Department of Biomaterials Science and Technology, University of Twente, Enschede, The Netherlands; Department of Biomedical Engineering, University Medical Center Groningen, University of Groningen, Groningen, The Netherlands.
authors.forename: Dirk W
authors.initials: DW
authors.lastname: Grijpma
authors.affiliation: AO Research Institute Davos, Davos Platz, Switzerland.
authors.forename: Matteo
authors.initials: M
authors.lastname: D'Este
mesh_terms: D001672:Biocompatible Materials / Q000737:chemistry*; D002082:Butylamines / Q000737:chemistry*; D004548:Elasticity; D006820:Hyaluronic Acid / Q000737:chemistry*; D009025:Morpholines / Q000737:chemistry*; D011437:Propylamines / Q000737:chemistry*; D014783:Viscosity
chemical_list: C467606:4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride; D001672:Biocompatible Materials; D002082:Butylamines; D009025:Morpholines; D011437:Propylamines; D006820:Hyaluronic Acid
keywords: 4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride; Alkyl derivatives; Amidation; Hyaluronic acid; Rheological properties