Journal
ACS CHEMICAL BIOLOGY
Volume 16, Issue 3, Pages 452-456Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acschembio.0c00823
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Funding
- New York University
- NIH [OD016343]
- German Academic Scholarship Foundation
- NCI [1F99CA253758-01]
- Deutsche Forschungsgemeinschaft [SFB944-P14, HO3539/1-1]
- National Science Foundation [MCB1817468]
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Short ceramide analogs with enhanced cell permeability and optical control of apoptosis have been developed, which can also function as photo-switchable substrates for sphingomyelin synthase 2, showing inverted light-dependence compared to their long-chain analogs.
We report short ceramide analogs that can be activated with light and further functionalized using azide-alkyne click chemistry. These molecules, termed scaCers, exhibit increased cell permeability compared to their long-chain analogs as demonstrated using mass spectrometry and imaging. Notably, scaCers enable optical control of apoptosis, which is not observed with long-chain variants. Additionally, they function as photo-switchable substrates for sphingomyelin synthase 2 (SMS2), exhibiting inverted light-dependence compared to their extended analogs.
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