Gelatin-Based Hydrogels through Homobifunctional Triazolinediones Targeting Tyrosine Residues

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 impr...

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Published inMolecules (Basel, Switzerland) Vol. 24; no. 3; p. 589
Main Authors Guizzardi, Roberto, Vaghi, Luca, Marelli, Marcello, Natalello, Antonino, Andreosso, Ivan, Papagni, Antonio, Cipolla, Laura
Format Journal Article
LanguageEnglish
Published Switzerland MDPI AG 07.02.2019
MDPI
Subjects
Amino acids
Biomaterials
Biomedical materials
Biopolymers
chemical cross-linking
Chemistry
Crosslinking
cyclic diazodicarboxamides
Drug delivery
Drug delivery systems
Drug development
ene-type chemistry
Gelatin
Hexanes
hydrogel
Hydrogels
natural polymers
Proteins
Residues
Thermal stability
Tissue engineering
triazolinediones
Triazolines
Tyrosine
triazolinediones
natural polymers
ene-type chemistry
hydrogel
chemical cross-linking
cyclic diazodicarboxamides
tyrosine
gelatin
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Summary: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(4 )-diones, namely 4,4'-hexane-1,6-diylbis(3 -1,2,4-triazoline-3,5(4 )-dione) and 4,4'-[methylenebis(4,1-phenylene)] (3 -1,2,4-triazoline-3,5(4 )-dione) 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.
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These authors contributed equally to this work.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules24030589