| Institution: | 1. Department of Chemistry and Biochemistry, University of California, Santa Barbara, Santa Barbara, CA, 93106 USA;2. Department of Molecular, Cellular and Developmental Biology, University of California, Santa Barbara, Santa Barbara, CA, 93106 USA;3. Department of Chemistry and Biochemistry, University of California, Santa Barbara, Santa Barbara, CA, 93106 USA
Department of Chemistry, New Mexico Highlands University, Las Vegas, NM, 87701 USA;4. BioPACIFIC Materials Innovation Platform, University of California, Santa Barbara, Santa Barbara, CA, 93106 USA |
| 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. |
