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Biomacromolecules. 2017 Mar 13;18(3):683-694. doi: 10.1021/acs.biomac.6b01355. Epub 2017 Feb 8.

Dual-Functional Hydrazide-Reactive and Anhydride-Containing Oligomeric Hydrogel Building Blocks.

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Institute of Pharmacy, Pharmaceutical Technology, Leipzig University , Eilenburger Straße 15 a, 04317 Leipzig, Germany.
Collaborative Research Center (SFB/Transregio 67), Matrixengineering, Leipzig and Dresden, Germany.
Biomaterials Department, INNOVENT e.V. , Prüssingstraße 27 b, 07745 Jena, Germany.
Institute of Organic Chemistry and Macromolecular Chemistry, Friedrich-Schiller University Jena , Humboldtstraße 10, 07743 Jena, Germany.


Biomimetic hydrogels are advanced biomaterials that have been developed following different synthetic routes. Covalent postfabrication functionalization is a promising strategy to achieve efficient matrix modification decoupled of general material properties. To this end, dual-functional macromers were synthesized by free radical polymerization of maleic anhydride with diacetone acrylamide (N-(1,1-dimethyl-3-oxobutyl)acrylamide) and pentaerythritol diacrylate monostearate. Amphiphilic oligomers (Mn < 7.5 kDa) with anhydride contents of 7-20% offered cross-linking reactivity to yield rigid hydrogels with gelatinous peptides (E = 4-13 kPa) and good cell adhesion properties. Mildly reactive methyl ketones as second functionality remained intact during hydrogel formation and potential of covalent matrix modification was shown using hydrazide and hydrazine model compounds. Successful secondary dihydrazide cross-linking was demonstrated by an increase of hydrogel stiffness (>40%). Efficient hydrazide/hydrazine immobilization depending on solution pH, hydrogel ketone content as well as ligand concentration for bioconjugation was shown and reversibility of hydrazone formation was indicated by physiologically relevant hydrazide release over 7 days. Proof-of-concept experiments with hydrazido-functionalized hyaluronan demonstrated potential for covalent aECM immobilization. The presented dual-functional macromers have perspective as reactive hydrogel building blocks for various biomedical applications.

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