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

0558318 - ÚOCHB 2023 RIV DE eng J - Článek v odborném periodiku
Poryvai, Anna - Galkin, Maksym - Shvadchak, Volodymyr - Slanina, Tomáš
Red-Shifted Water-Soluble BODIPY Photocages for Visualisation and Controllable Cellular Delivery of Signaling Lipids.
Angewandte Chemie - International Edition. Roč. 61, č. 34 (2022), č. článku e202205855. ISSN 1433-7851. E-ISSN 1521-3773
Grant CEP: GA ČR(CZ) GA22-20319S
Institucionální podpora: RVO:61388963
Klíčová slova: BODIPY * photocages * selective delivery * signaling lipids * uncaging
Obor OECD: Organic chemistry
Impakt faktor: 16.6, rok: 2022
Způsob publikování: Omezený přístup
https://doi.org/10.1002/anie.202205855

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.
Trvalý link: http://hdl.handle.net/11104/0332044