Family of BODIPY Photocages Cleaved by Single Photons of Visible/Near-Infrared Light

Family of BODIPY Photocages Cleaved by Single Photons of Visible/Near-Infrared Light

Photocages are light-sensitive chemical protecting groups that provide external control over when, where, and how much of a biological substrate is activated in cells using targeted light irradiation. Regrettably, most popular photocages (e.g., o-nitrobenzyl groups) absorb cell-damaging ultraviolet...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2018-06, Vol.140 (23), p.7343-7346
Main Authors: Peterson, Julie A, Wijesooriya, Chamari, Gehrmann, Elizabeth J, Mahoney, Kaitlyn M, Goswami, Pratik P, Albright, Toshia R, Syed, Aleem, Dutton, Andrew S, Smith, Emily A, Winter, Arthur H
Format: Article
Language:eng
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Summary:Photocages are light-sensitive chemical protecting groups that provide external control over when, where, and how much of a biological substrate is activated in cells using targeted light irradiation. Regrettably, most popular photocages (e.g., o-nitrobenzyl groups) absorb cell-damaging ultraviolet wavelengths. A challenge with achieving longer wavelength bond-breaking photochemistry is that long-wavelength-absorbing chromophores have shorter excited-state lifetimes and diminished excited-state energies. However, here we report the synthesis of a family of BODIPY-derived photocages with tunable absorptions across the visible/near-infrared that release chemical cargo under irradiation. Derivatives with appended styryl groups feature absorptions above 700 nm, yielding photocages cleaved with the highest known wavelengths of light via a direct single-photon-release mechanism. Photorelease with red light is demonstrated in living HeLa cells, Drosophila S2 cells, and bovine GM07373 cells upon ∼5 min irradiation. No cytotoxicity is observed at 20 μM photocage concentration using the trypan blue exclusion assay. Improved B-alkylated derivatives feature improved quantum efficiencies of photorelease ∼20-fold larger, on par with the popular o-nitrobenzyl photocages (εΦ = 50–100 M–1 cm–1), but absorbing red/near-IR light in the biological window instead of UV light.
ISSN:0002-7863
1520-5126