The DOI matches its Crossref record; 30 of the 30 references it cites were found in a registry or an index.
Family of BODIPY Photocages Cleaved by Single Photons of Visible/Near-Infrared Light
Abstract
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.
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Metadata
- Authors
- Peterson, J. A., Wijesooriya, C., Gehrmann, E. J., Mahoney, K. M., Goswami, P. P., Albright, T. R., Syed, A., Dutton, A. S., Smith, E. A., & Winter, A. H.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2018-05-18
- Volume
- 140
- Issue
- 23
- Pages
- 7343-7346
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2805009740
- Cited by
- 299
- References
- 30
- FWCI
- 10.03
- Type
- journal article
- Language
- en
- Open access
- closed
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