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

Abstract

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.

Non-aryl substituted aza-BODIPYs at 1,7- or 3,5-sites: synthesis, structures, optical properties, and applications

“…1 Near-infrared (NIR) absorbing aza-BODIPY chromophores have excellent photophysical properties, such as the reduction of background absorption and light scattering, deep penetration in tissues to allow in vivo imaging and photodynamic therapy (PDT), and photothermal therapy (PTT). [2][3][4][5][6][7] Therefore, aza-BODIPYs have been extensively applied in chemical sensors, [8][9][10][11][12] fluorescent dyes, [13][14][15][16][17] laser dyes, [18][19][20] organic photoelectric device, [21][22][23][24][25] dye photosensitizers, [26][27][28][29][30][31][32] photothermal agents, [33][34][35][36][37][38] and other fields. In particular, the NIR chromophores endowed dyes high sensitivity in biological detection with little photodamage to biological tissues and are more suitable for biological diagnosis and phototherapeutics.…”

An organelle-specific photoactivation and dual-isotope labeling strategy reveals phosphatidylethanolamine metabolic flux

“…Photocaging has been applied to a number of lipid messengers like phosphoinositides, 3 diacylglycerides, 4 ceramides 5 and fatty acids. 6,7 While these studies focused on the roles of lipids in signalling processes, examples of photocaging tools to trace their metabolism are rare. In the past few years, our group has developed a series of photocaged lipids targeting different subcellular compartments including lysosomes and mitochondria.…”

Organelle-specific photoactivation and dual-isotope labeling strategy reveals phosphatidylethanolamine metabolic flux

“…Photocaging has been applied to a number of lipid messengers like phosphoinositides, 3 diacylglycerides, 4 ceramides 5 and fatty acids. 6,7 While these studies focused on lipid roles in signalling processes, examples of photocaging tools to trace their metabolism are rare. In the past years, our group has developed a series of photocaged lipids targeted to different subcellular compartments including lysosomes and mitochondria.…”