1192846-07-3Relevant academic research and scientific papers
Synthesis and evaluation of sphingolipid analogues modification of the hydroxy group at C(1) of 7-oxasphingosine, and of the hydroxy group at C(1) and the amide group of 7-oxaceramides
Mathew, Thresen,Billich, Andreas,Cavallari, Marco,Bornancin, Frederic,Nussbaumer, Peter,De Libero, Gennaro,Vasella, Andrea
experimental part, p. 705 - 724 (2010/04/23)
The analogues 7-9 of 7-oxaceramide and 7-oxasphingosine were synthesized from the known azidosphingosine 21. The 1,4-disubstituted 1,2,3-triazole analogues 10-16 of ceramides were synthesized by the click reaction of the known azide 24. None of the analogues 7-15 was active as inhibitor of SPHK type 1 and of acid sphingomyelinase, whereas 16 is a weak inhibitor of SPHK1. Triazoles 10, 11, and 15 did not inhibit ceramide phosphorylation by CerK, and none of 7, 8, and 10-15 activated invariant natural killer T (iNKT) cell clones when presented by human CD1d-transfected antigen-presenting cells (APC) or by plate-bound human CD1d [55]. Triazoles 14 and 15 prevent binding of α-galactosylceramide (α-GalCer) to plate-bound human CD1d and subsequent T-cell response to α-GalCer. Only 15 reduced activation by α-GalCer significantly and independently of the cytokine measured.
