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.
Keywords: BODIPY; Photocages; Selective Delivery; Signaling Lipids; Uncaging.
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