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Synthesis and characterization of bichromophoric 1-deoxyceramides as FRET probes

AuthorsIzquierdo, Eduardo; Casasampere, Mireia; Fabriàs, Gemma CSIC ORCID; Abad, José Luis CSIC ORCID ; Casas, Josefina CSIC ORCID ; Delgado Cirilo, Antonio
FRET probes
Issue Date23-Feb-2021
PublisherRoyal Society of Chemistry (UK)
CitationOrganic and Biomolecular Chemistry 19: 2456-2467 (2021)
AbstractThe suitability as FRET probes of two bichromophoric 1-deoxydihydroceramides containing a labelled spisulosine derivative as a sphingoid base and two differently ω-labelled fluorescent palmitic acids has been evaluated. The ceramide synthase (CerS) catalyzed metabolic incorporation of ω-azido palmitic acid into the above labeled spisulosine to render the corresponding ω-azido 1-deoxyceramide has been studied in several cell lines. In addition, the strain-promoted click reaction between this ω-azido 1-deoxyceramide and suitable fluorophores has been optimized to render the target bichromophoric 1-deoxydihydroceramides. These results pave the way for the development of FRET-based assays as a new tool to study sphingolipid metabolism.
Publisher version (URL)https://doi.org/10.1039/D1OB00113B
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