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Charged Triazole Cross-Linkers for Hyaluronan-Based Hybrid Hydrogels

Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, Stuttgart D-70569, Germany
Department of Cellular Biophysics & CSF Biomaterials, Max-Planck Institute for Medical Research, Heidelberg D-69120, Germany
Department of Biophysical Chemistry, University of Heidelberg, Im Neuenheimerfeld 253, Heidelberg D-69120, Germany
Institut für Grenzflächenverfahrenstechnik und Plasmatechnologie IGVP, Universität Stuttgart, Nobelstr. 12, Stuttgart D-70569, Germany
Fraunhofer-Institut für Grenzflächen- und Bioverfahrenstechnik IGB, Nobelstr. 12, Stuttgart D-70569, Germany
Authors to whom correspondence should be addressed.
These authors contributed equally to this work.
Academic Editor: Franz E. Weber
Materials 2016, 9(10), 810;
Received: 28 July 2016 / Revised: 13 September 2016 / Accepted: 23 September 2016 / Published: 30 September 2016
(This article belongs to the Special Issue Smart Hydrogels for (Bio)printing Applications)
PDF [1164 KB, uploaded 30 September 2016]


Polyelectrolyte hydrogels play an important role in tissue engineering and can be produced from natural polymers, such as the glycosaminoglycan hyaluronan. In order to control charge density and mechanical properties of hyaluronan-based hydrogels, we developed cross-linkers with a neutral or positively charged triazole core with different lengths of spacer arms and two terminal maleimide groups. These cross-linkers react with thiolated hyaluronan in a fast, stoichiometric thio-Michael addition. Introducing a positive charge on the core of the cross-linker enabled us to compare hydrogels with the same interconnectivity, but a different charge density. Positively charged cross-linkers form stiffer hydrogels relatively independent of the size of the cross-linker, whereas neutral cross-linkers only form stable hydrogels at small spacer lengths. These novel cross-linkers provide a platform to tune the hydrogel network charge and thus the mechanical properties of the network. In addition, they might offer a wide range of applications especially in bioprinting for precise design of hydrogels. View Full-Text
Keywords: hyaluronan; triazole; triazolium; hydrogels; cross-linking hyaluronan; triazole; triazolium; hydrogels; cross-linking

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Martini, M.; Hegger, P.S.; Schädel, N.; Minsky, B.B.; Kirchhof, M.; Scholl, S.; Southan, A.; Tovar, G.E.M.; Boehm, H.; Laschat, S. Charged Triazole Cross-Linkers for Hyaluronan-Based Hybrid Hydrogels. Materials 2016, 9, 810.

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