Enhancing hyaluronan pseudoplasticity via 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride-mediated conjugation with short alkyl moieties

Dalila Petta; David Eglin; Dirk W Grijpma; Matteo D'Este

doi:10.1016/j.carbpol.2016.05.096

Enhancing hyaluronan pseudoplasticity via 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride-mediated conjugation with short alkyl moieties

Carbohydr Polym. 2016 Oct 20:151:576-583. doi: 10.1016/j.carbpol.2016.05.096. Epub 2016 May 28.

Authors

Dalila Petta¹, David Eglin², Dirk W Grijpma³, Matteo D'Este²

Affiliations

¹ 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.
² AO Research Institute Davos, Davos Platz, Switzerland.
³ 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.

PMID: 27474602
DOI: 10.1016/j.carbpol.2016.05.096

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.

Keywords: 4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride; Alkyl derivatives; Amidation; Hyaluronic acid; Rheological properties.

MeSH terms

Biocompatible Materials / chemistry*
Butylamines / chemistry*
Elasticity
Hyaluronic Acid / chemistry*
Morpholines / chemistry*
Propylamines / chemistry*
Viscosity

Substances

4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride
Biocompatible Materials
Butylamines
Morpholines
Propylamines
Hyaluronic Acid