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

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.

journal_name

Chem Phys Lipids

authors

Kim YA,Day J,Lirette CA,Costain WJ,Johnston LJ,Bittman R

doi

10.1016/j.chemphyslip.2015.07.006

subject

Has Abstract

pub_date

2016-01-01 00:00:00

pages

117-24

eissn

0009-3084

issn

1873-2941

pii

S0009-3084(15)30011-6

journal_volume

194

pub_type

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