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Molecules 2019, 24(3), 589; https://doi.org/10.3390/molecules24030589

Gelatin-Based Hydrogels through Homobifunctional Triazolinediones Targeting Tyrosine Residues

1
Department of Biotechnology and Biosciences, University of Milano—Bicocca, Piazza della Scienza 2, 20126 Milano-IT, Italy
2
Department of Materials Science, University of Milano—Bicocca, via R. Cozzi 55, 20125 Milano-IT, Italy
3
CNR, Institute of Molecular Science and Technologies, Via C. Golgi 19, 20133 Milano-IT, Italy
*
Authors to whom correspondence should be addressed.
These authors contributed equally to this work.
Received: 17 January 2019 / Revised: 5 February 2019 / Accepted: 5 February 2019 / Published: 7 February 2019
(This article belongs to the Special Issue Molecules for Biotechnologies)
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Abstract

Gelatin is a biopolymer with interesting properties that can be useful for biomaterial design for different applications such as drug delivery systems, or 3D scaffolds for tissue engineering. However, gelatin suffers from poor mechanical stability at physiological temperature, hence methods for improving its properties are highly desirable. In the present work, a new chemical cross-linking strategy based on triazolinedione ene-type chemistry towards stable hydrogel is proposed. Two different homobifunctional 1,2,4-triazoline-3,5(4H)-diones, namely 4,4′-hexane-1,6-diylbis(3H-1,2,4-triazoline-3,5(4H)-dione) 1 and 4,4′-[methylenebis(4,1-phenylene)]bis(3H-1,2,4-triazoline-3,5(4H)-dione) 2 were used as cross-linkers in different ratio to tyrosine residues in gelatin. The reaction was proved effective in all experimented conditions and hydrogels featured with different thermal stability were obtained. In general, the higher the cross-linker/tyrosine ratio, the more thermostable the hydrogel. The swelling properties are strictly dependent upon the chemical nature of the cross-linker. View Full-Text
Keywords: gelatin; hydrogel; ene-type chemistry; tyrosine; triazolinediones; cyclic diazodicarboxamides; chemical cross-linking; natural polymers gelatin; hydrogel; ene-type chemistry; tyrosine; triazolinediones; cyclic diazodicarboxamides; chemical cross-linking; natural polymers
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Guizzardi, R.; Vaghi, L.; Marelli, M.; Natalello, A.; Andreosso, I.; Papagni, A.; Cipolla, L. Gelatin-Based Hydrogels through Homobifunctional Triazolinediones Targeting Tyrosine Residues. Molecules 2019, 24, 589.

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