Short Soluble Coumarin Crosslinkers for Light-Controlled Release of Cells and Proteins from Hydrogels

Materials that degrade or dissociate in response to low power light promise to enable on-demand, precisely localized delivery of drugs or bioactive molecules in living systems. Such applications remain elusive because few materials respond to wavelengths that appreciably penetrate tissues. The photo...

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Bibliographic Details
Published in:Biomacromolecules 2015-10, Vol.16 (10), p.3286-3296
Main Authors: de Gracia Lux, Caroline, Lux, Jacques, Collet, Guillaume, He, Sha, Chan, Minnie, Olejniczak, Jason, Foucault-Collet, Alexandra, Almutairi, Adah
Format: Article
Language:English
Subjects:
Animals
Cells, Cultured
Chemical Sciences
Chromatography, High Pressure Liquid
Coumarins - chemistry
Cross-Linking Reagents - chemistry
Hydrogels - chemistry
Life Sciences
Light
Mass Spectrometry
Mice
Mice, Inbred C57BL
Microscopy, Electron, Transmission
Proteins - chemistry
Solubility
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Summary:Materials that degrade or dissociate in response to low power light promise to enable on-demand, precisely localized delivery of drugs or bioactive molecules in living systems. Such applications remain elusive because few materials respond to wavelengths that appreciably penetrate tissues. The photocage bromohydroxycoumarin (Bhc) is efficiently cleaved upon low-power ultraviolet (UV) and near-infrared (NIR) irradiation through one- or two-photon excitation, respectively. We have designed and synthesized a short Bhc-bearing crosslinker to create light-degradable hydrogels and nanogels. Our crosslinker breaks by intramolecular cyclization in a manner inspired by the naturally occurring ornithine lactamization, in response to UV and NIR light, enabling rapid degradation of polyacrylamide gels and release of small hydrophilic payloads such as an ∼10 nm model protein and murine mesenchymal stem cells, with no background leakage.
ISSN:1525-7797
1526-4602
DOI:10.1021/acs.biomac.5b00950