Red-Shifted Water-Soluble BODIPY Photocages for Visualisation and Controllable Cellular Delivery of Signaling Lipids.

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 (λ irr =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 Ca 2+ release in cells expressing the GPR40 receptor.