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  1. Abstract

    Spatiotemporally functionalized hydrogels have exciting applications in tissue engineering, but their preparation often relies on radical‐based strategies that can be deleterious in biological settings. Herein, the computationally guided design, synthesis, and application of a water‐soluble cyclopentadienone‐norbornadiene (CPD‐NBD) adduct is disclosed as a diene photocage for radical‐free Diels‐Alder photopatterning. We show that this scalable CPD‐NBD derivative is readily incorporated into hydrogel formulations, providing gels that can be patterned with dienophiles upon 365 nm uncaging of cyclopentadiene. Patterning is first visualized through conjugation of cyanine dyes, then biological utility is highlighted by patterning peptides to direct cellular adhesion. Finally, the ease of use and versatility of this CPD‐NBD derivative is demonstrated by direct incorporation into a commercial 3D printing resin to enable the photopatterning of structurally complex, printed hydrogels.

     
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  2. Strategies that mimic the spatial complexity of natural tissues can provide cellular scaffolds to probe fundamental questions in cell biology and offer new materials for regenerative medicine. Here, we demonstrate a light‐guided patterning platform that uses natural ECM‐proteins as a substrate to program cellular behaviors. We utilize a photocaged diene which undergoes Diels–Alder based click chemistry upon uncaging with 365 nm light. By interfacing with commercially available maleimide dienophiles, we achieve patterning of common ECM proteins (collagen, fibronectin Matrigel, laminin) with readily purchased functional small molecules and growth factors. Finally, we highlight the use of this platform to spatially control ERK activity and migration in mammalian cells, demonstrating programmable cell behavior through patterned chemical modification of natural ECM. 
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    Free, publicly-accessible full text available August 23, 2024