Design, Synthesis, and Application of a Water-soluble Photocage for Aqueous Cyclopentadiene-based Diels-Alder Photoclick Chemistry in Hydrogels
© 2023 Wiley-VCH GmbH..
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.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2023 |
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| Erschienen: |
2023 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:62 |
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| Enthalten in: |
Angewandte Chemie (International ed. in English) - 62(2023), 16 vom: 11. Apr., Seite e202301157 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Bailey, Sophia J [VerfasserIn] |
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| Links: |
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| Themen: |
3D Printing |
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| Anmerkungen: |
Date Completed 03.04.2023 Date Revised 03.04.2023 published: Print-Electronic Citation Status PubMed-not-MEDLINE |
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| doi: |
10.1002/anie.202301157 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| 520 | |a © 2023 Wiley-VCH GmbH. | ||
| 520 | |a 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 | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a 3D Printing | |
| 650 | 4 | |a Cyclopentadiene | |
| 650 | 4 | |a Diels-Alder | |
| 650 | 4 | |a Hydrogels | |
| 650 | 4 | |a Photoclick | |
| 700 | 1 | |a Hopkins, Erik |e verfasserin |4 aut | |
| 700 | 1 | |a Rael, Kiara D |e verfasserin |4 aut | |
| 700 | 1 | |a Hashmi, Arsalan |e verfasserin |4 aut | |
| 700 | 1 | |a Urueña, Juan Manuel |e verfasserin |4 aut | |
| 700 | 1 | |a Wilson, Maxwell Z |e verfasserin |4 aut | |
| 700 | 1 | |a Read de Alaniz, Javier |e verfasserin |4 aut | |
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