Red-Shifted Water-Soluble BODIPY Photocages for Visualisation and Controllable Cellular Delivery of Signaling Lipids
Language English Country Germany Media print-electronic
Document type Journal Article, Research Support, Non-U.S. Gov't
- Keywords
- BODIPY, Photocages, Selective Delivery, Signaling Lipids, Uncaging,
- MeSH
- Lipids MeSH
- Boron Compounds * chemistry MeSH
- Light MeSH
- Water * MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
- Names of Substances
- 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene MeSH Browser
- Lipids MeSH
- Boron Compounds * MeSH
- Water * MeSH
In this work, we developed a water-soluble caging group based on a π-extended BODIPY scaffold able to release carboxylate-containing cargo upon red light illumination (λirr =633 nm). We performed mechanistic studies showing new insights into the principles of the photoreactivity of these cages and demonstrated a significant influence of the structure of a carboxylate cargo on the rate and efficiency of the uncaging process and its side reactions. We used it for selective delivery, visualisation, and photorelease of a signaling lipid in cell plasma and internal membranes. With this approach, we successfully induced Ca2+ release in cells expressing the GPR40 receptor.
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