Short Photoswitchable Ceramides Enable Optical Control of Apoptosis
Creators
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1.
New York University
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2.
California Institute of Technology
Abstract
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 photoswitchable substrates for sphingomyelin synthase 2 (SMS2), exhibiting inverted light-dependence compared to their extended analogs.
Copyright and License
Copyright © 2021 American Chemical Society
Acknowledgement
We thank New York University for financial support. NMR spectra were acquired using the TCI cryoprobe supported by the NIH (OD016343). J.M. and K.H. thank the German Academic Scholarship Foundation for a fellowship, and J.M. and A.J.N. thank the New York University for a MacCracken Ph.D. fellowship. J.M. thanks New York University for a Margaret and Herman Sokol fellowship, and the NCI for a F99/K00 award (1F99CA253758-01). J.C.M.H. acknowledges support from the Deutsche Forschungsgemeinschaft (SFB944-P14 and HO3539/1-1). G.E.A.G. acknowledges the support from the National Science Foundation (MCB1817468). G.P. thanks New York University for a Dean’s Undergraduate Research Fund (DURF) Grant.
Additional Information
The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acschembio.0c00823.
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Experimental details, NMR spectra, photophysical characterization (PDF)
Files
cb0c00823_si_001.pdf
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Additional details
Identifiers
- ISSN
- 1554-8937
Related works
- Is supplemented by
- Supplemental Material: https://pubs.acs.org/doi/suppl/10.1021/acschembio.0c00823/suppl_file/cb0c00823_si_001.pdf (URL)
Funding
- National Cancer Institute
- 1F99CA253758-01
- Division of Molecular & Cellular Biosciences
- MCB1817468
- German Academic Exchange Service
- Deutsche Forschungsgemeinschaft
- HO3539/1-1
- Deutsche Forschungsgemeinschaft
- SFB944-P14
- New York University
Dates
- Available
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2021-02-15Published online