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

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DOIResolve DOI: http://doi.org/10.1016/j.chemphyslip.2015.07.006
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TypeArticle
Journal titleChemistry and Physics of Lipids
ISSN0009-3084
SubjectCeramide; PEGylated coumarin cages; Photocage; Photolysis
AbstractCaged 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
LanguageEnglish
AffiliationMeasurement Science and Standards; Human Health Therapeutics; National Research Council Canada
Peer reviewedYes
NPARC number21276959
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Record identifier69f75db9-fd7a-4a2e-b188-915b0a745278
Record created2015-11-10
Record modified2016-05-09
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