Synthesis and photochemical properties of PEGylated coumarin-caged ceramides for cell studies
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Updated: Apr 6, 2026
Design, Synthesis, and Photochemical Properties of Clickable Caged Compounds
Published on: October 15, 2019
Young Ah Kim1, Jenna Day2, Carol Ann Lirette2
1Department of Chemistry and Biochemistry, Queens College of The City University of New York, Flushing, NY 11367, USA.
Abstract:
Caged ceramide analogues (C6-, C16-, C18-, C22- and C24-Cer) have been prepared by introducing a hydrophilic coumarin-based cage bearing a short polyethylene glycol (PEG) chain. (6-Bromo-7-mTEGylated-coumarin-4-yl)methyl (Btc) caged ceramide showed efficient photo-uncaging to release the parent ceramide upon direct exposure to 350 nm UV light; in contrast (7-mTEGylated-coumarin-4-yl)methyl (Tc) caged ceramide was photolysed more slowly. In preliminary experiments, Btc-caged ceramides were taken up by cells and their photolysis led to decreases in cell viability, but not to activation of caspase enzymes, suggesting that either reactive oxygen species or an alternate caspase-independent pathway may be responsible for the decreases in cell viability caused by photolysis of caged ceramides.
