Caged Ceramide 1-Phosphate Analogues: Synthesis and Properties

Caged Ceramide 1-Phosphate Analogues: Synthesis and Properties

Sphingolipid phosphate analogues bearing 7-(diethylamino)coumarin (DECM) and 4-bromo-5-hydroxy-2-nitrobenzhydryl (BHNB) groups in a photolabile ester bond were synthesized. The ability of the “caged” ceramide 1-phosphate analogues to release the bioactive parent molecule upon irradiation at 400−500...

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Veröffentlicht in:Journal of organic chemistry 2009-11, Vol.74 (22), p.8844-8847
Hauptverfasser: Lankalapalli, Ravi S, Ouro, Alberto, Arana, Lide, Gómez-Muñoz, Antonio, Bittman, Robert
Format: Artikel
Sprache:eng
Schlagworte:
Ceramides - chemical synthesis
Ceramides - chemistry
Chemistry
Exact sciences and technology
General and physical chemistry
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Lipids
Molecular Structure
Organic chemistry
Photochemistry
Physical chemistry of induced reactions (with radiations, particles and ultrasonics)
Preparations and properties
Stereoisomerism
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Zusammenfassung:Sphingolipid phosphate analogues bearing 7-(diethylamino)coumarin (DECM) and 4-bromo-5-hydroxy-2-nitrobenzhydryl (BHNB) groups in a photolabile ester bond were synthesized. The ability of the “caged” ceramide 1-phosphate analogues to release the bioactive parent molecule upon irradiation at 400−500 nm was demonstrated by stimulation of macrophage cell proliferation.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo902076w