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Synthesis and photochemical properties of PEGylated coumarin-caged ceramides for cell studies

From National Research Council Canada

DOIResolve DOI: https://doi.org/10.1016/j.chemphyslip.2015.07.006
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Name affiliation
  1. National Research Council of Canada. Measurement Science and Standards
  2. National Research Council of Canada. Human Health Therapeutics
FormatText, Article
Subjectceramide; PEGylated coumarin cages; photocage; photolysis
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.
Publication date
PublisherElsevier
In
  • Chemistry and Physics of Lipids 194: 117–124.
LanguageEnglish
Peer reviewedYes
NPARC number21276959
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Record identifier69f75db9-fd7a-4a2e-b188-915b0a745278
Record created2015-11-10
Record modified2020-04-22
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