Hydrogel Synthesis and Stabilization via Tetrazine Click-Induced Secondary Interactions.

Macromolecular Rapid Communications
Samantha E HoltDaniel L Alge

Abstract

The discovery of tetrazine click-induced secondary interactions is reported as a promising new tool for polymeric biomaterial synthesis. This phenomenon is first demonstrated as a tool for poly(ethylene glycol) (PEG) hydrogel assembly via purely non-covalent interactions and is shown to yield robust gels with storage moduli one to two orders of magnitude higher than other non-covalent crosslinking methods. In addition, tetrazine click-induced secondary interactions also enhance the properties of covalently crosslinked hydrogels. A head-to-head comparison of PEG hydrogels crosslinked with tetrazine-norbornene and thiol-norbornene click chemistry reveals an approximately sixfold increase in storage modulus and unprecedented resistance to hydrolytic degradation in tetrazine click-crosslinked gels without substantial differences in gel fraction. Molecular dynamic simulations attribute these differences to the presence of secondary interactions between the tetrazine-norbornene cycloaddition products, which are absent in the thiol-norbornene crosslinked gels.

References

Jan 24, 2009·Langmuir : the ACS Journal of Surfaces and Colloids·Nadia TzokovaAnthony J Ryan
Aug 24, 2011·Chemical Communications : Chem Comm·Pedro Ramírez-LópezMiguel A Sierra
May 23, 2014·Journal of Controlled Release : Official Journal of the Controlled Release Society·Widya MulyasasmitaSarah C Heilshorn
Sep 2, 2014·ACS Macro Letters·Han ZhangJoseph M Fox
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Jan 26, 2016·Advanced Healthcare Materials·Sandeep T KoshyDavid J Mooney
Aug 8, 2018·Biomaterials·Aline LueckgenAmaia Cipitria

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Citations

Sep 15, 2020·Advanced Biosystems·Matthew R ArkenbergChien-Chi Lin
Aug 14, 2020·Bioconjugate Chemistry·Asli Z Unal, Jennifer L West
Aug 10, 2021·ACS Biomaterials Science & Engineering·Min Hee KimChien-Chi Lin

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