Precise tailoring of tyramine-based hyaluronan hydrogel properties using DMTMM conjugation

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Author(s) Loebel, Claudia, D'Este, Matteo, Alini, Mauro, Zenobi-Wong, Marcy, Eglin, David
Publication Type Journal Items, Publication Status: Published
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Title Precise tailoring of tyramine-based hyaluronan hydrogel properties using DMTMM conjugation
Author(s) Loebel, Claudia
D'Este, Matteo
Alini, Mauro
Zenobi-Wong, Marcy
Eglin, David
Journal or Series Title Carbohydrate Polymers
Volume Number 115
Start Page 325
End Page 333
ISSN 0144-8617
Publisher Elsevier
Publication Place Amsterdam
Publication Date 2015-01
Keyword(s) Hyaluronic acid
Tyramine 4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride
Abstract Injectable tyramine modified hyaluronic acid (HA-Tyr) hydrogels which are bio-orthogonally crosslinked with horseradish peroxidase (HRP) and hydrogen peroxide (H2O2) are excellent candidate biomaterials for drug delivery, regenerative medicine and tissue engineering. Ligation of tyramine to HA has been reported using the very well established N-(3-dimethylaminopropy1)-M-ethylcarbodiimide hydrochloride (EDC) and N-hydroxysuccinimide (NHS) chemistry. Here we demonstrate the applicability of 4-(4,6-dimethoxy-1,3,5-triazin-2-y1)-4-methylmorpholinium chloride (DMTMM) as an alternative coupling agent to synthesize HA-Tyr conjugates. The optimized derivatization process allows accurate control of the degree of substituted Tyr on hyaluronan (DSmoi). Hence, viscoelastic properties, in vitro swelling and enzymatic digestion profiles of the crosslinked hydrogels can be precisely tuned via DS,-noi. Our study demonstrates the advantages of DMTMM conjugation as a powerful tool to synthesize HA-Tyr hydrogels with properties exactly tailored for biomedical applications.
DOI 10.1016/j.carbpol.2014.08.097
Additional Notes Received 30 June 2014, Received in revised form 13 August 2014, Accepted 15 August 2014, Available online 15 September 2014
Document Type Article
Publication Status Published
Language English
Assigned Organisational Unit(s) 03949
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NEBIS System Number 000013805
Source Database ID WOS-000344869800042
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  author = "Loebel, Claudia and D'Este, Matteo and Alini, Mauro and Zenobi-Wong, Marcy and Eglin, David",
  title = "{P}recise tailoring of tyramine-based hyaluronan hydrogel properties using {D}{M}{T}{M}{M} conjugation",
  journal = "Carbohydrate Polymers",
  year = 2015,
  volume = "115",
  pages = "325--333",
  month = jan,

E-Citations record created: Wed, 14 Jan 2015, 10:12:30 CET