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 (λirr=633 nm). We performed mechanistic studies showing new insights into the principles of the photoreactivity of these cages and de...

Full description

Saved in:
Bibliographic Details
Published in:Angewandte Chemie International Edition 2022-08, Vol.61 (34), p.e202205855-n/a
Main Authors: Poryvai, Anna, Galkin, Maksym, Shvadchak, Volodymyr, Slanina, Tomáš
Format: Article
Language:English
Subjects:
BODIPY
Calcium ions
Cargo
Lipids
Photocages
Selective Delivery
Side reactions
Signaling
Signaling Lipids
Uncaging
Visualization
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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. Water‐soluble π‐extended BODIPY photocages are presented. They can selectively target inner or outer cell membranes and release signaling lipids upon red‐light illumination, inducing Ca2+ signaling. The solvent‐dependent uncaging mechanism and orthogonal uncaging in the presence of a coumarin‐caged lipid is reported.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.202205855