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 pi-extended BODIPY scaffold able to release carboxylate-containing cargo upon red light illumination (lambda(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 Ca2+ release in cells expressing the GPR40 receptor.

Automated summary

In this work, a water-soluble caging group based on a pi-extended BODIPY scaffold was developed to release carboxylate-containing cargo upon red light illumination. Mechanistic studies showed new insights into the photoreactivity of these cages, and the structure of the carboxylate cargo was found to significantly influence the rate and efficiency of the uncaging process. The method was successfully used for selective delivery, visualization, and photorelease of a signaling lipid in cell plasma and internal membranes, inducing Ca2+ release in cells expressing the GPR40 receptor.