化学
紧身衣
光化学
发色团
激发态
台盼蓝
波长
赫拉
紫外线
辐照
荧光
可见光谱
光电子学
红外线的
光学
细胞
材料科学
物理
核物理学
生物化学
作者
Julie Peterson,Chamari S. Wijesooriya,Elizabeth J. Gehrmann,Kaitlyn M. Mahoney,Pratik P. Goswami,Toshia Albright,Aleem Syed,Andrew S. Dutton,Emily A. Smith,Arthur H. Winter
摘要
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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