2014
DOI: 10.1021/mz5002993
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Interfacial Bioorthogonal Cross-Linking

Abstract: Described herein is interfacial bioorthogonal cross-linking, the use of bioorthogonal chemistry to create and pattern biomaterials through diffusion-controlled gelation at the liquid-gel interface. The basis is a rapid (k2 284000 M–1 s–1) reaction between strained trans-cyclooctene (TCO) and tetrazine (Tz) derivatives. Syringe delivery of Tz-functionalized hyaluronic acid (HA-Tz) to a bath of bis-TCO cross-linker instantly creates microspheres with a cross-linked shell through which bis-TCO diffuses freely to … Show more

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Cited by 62 publications
(83 citation statements)
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References 46 publications
(74 reference statements)
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“…Because the crosslinking is diffusion controlled, hydrogel spheres with 3D spatial patterns (Figure 4A) and water-filled hydrogel channels (Figure 4B) can be fabricated readily without the need for external templates or stimuli. 51 These bioorthogonal hydrogel platforms are being explored for the in vitro assembly of secretory acini with interconnected ducts.…”
Section: Biomaterials Strategymentioning
confidence: 99%
See 1 more Smart Citation
“…Because the crosslinking is diffusion controlled, hydrogel spheres with 3D spatial patterns (Figure 4A) and water-filled hydrogel channels (Figure 4B) can be fabricated readily without the need for external templates or stimuli. 51 These bioorthogonal hydrogel platforms are being explored for the in vitro assembly of secretory acini with interconnected ducts.…”
Section: Biomaterials Strategymentioning
confidence: 99%
“…( G ): Crosshatched multiblock copolymer mesh imaged under light microscope. Reprinted with permission from Zhang et al, 2014 (A–B), 51 Jia et al, 2006 (C), 52 Jha et al, 2009 (D), 56 and Soscia et al, 2013 (E) 28 and Liu et al, 2015 (F–G). 31 …”
Section: Figurementioning
confidence: 99%
“…Another impactful demonstration of the utility of the TCO/Tz reaction in polysaccharide chemistry was performed by the Jia and Fox groups [127]. In this work, the authors took advantage of the rapid reaction between Tz and TCO (rate constant k 2 > 10 5 M -1 s -1 has been measured [128]) to realize rapid diffusion-controlled interface crosslinking ( Figure 17).…”
Section: Inverse Electron Demand Diels-alder Reactionmentioning
confidence: 99%
“…(b) Gel interface forms when a droplet of tetrazine-modified hyaluronic (HA-Tz) contacts a solution of bis-transcyclooctene cross-linker (bis-TCO). Cross-linking at the gel/liquid interface is faster than the rate of diffusion through the gel interface [127],. Copyright 2014.…”
mentioning
confidence: 99%
“…154157 Pioneered by the Fox group, the Fox and Jia groups subsequently developed the tetrazine ligation for the production of polymers and polymer conjugates. 158 Jia and coworkers further reported the formation of block copolymers by interfacial bioorthogonal polymerization. The multiblock copolymer fibers were obtained by rapid reaction between sTCO and diphenyl-s-tetrazine (GGWGRGDSPG peptide tagged with PEG) PEG derivatives with immiscible liquid-liquid interfaces.…”
Section: Synthetic Strategies For Producing Peptide-polymer Conjugatesmentioning
confidence: 99%