Mathew, Thresen and Billich, Andreas and Cavallari, Marco and Bornancin, Frederic and Nussbaumer, Peter and De Libero, Gennaro and Vasella, Andrea. (2009) 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. Chemistry & biodiversity, Vol. 6. pp. 705-724.
Full text not available from this repository.
Official URL: http://edoc.unibas.ch/dok/A6003718
Downloads: Statistics Overview
Abstract
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 alpha-galactosylceramide (alpha-GalCer) to plate-bound human CD1d and subsequent T-cell response to alpha-GalCer. Only 15 reduced activation by alpha-GalCer significantly and independently of the cytokine measured.
Faculties and Departments: | 03 Faculty of Medicine > Departement Biomedizin > Department of Biomedicine, University Hospital Basel > Experimental Immunology (De Libero) |
---|---|
UniBasel Contributors: | De Libero, Gennaro |
Item Type: | Article, refereed |
Article Subtype: | Research Article |
Publisher: | Helvetica Chimica Acta |
ISSN: | 1612-1872 |
Note: | Publication type according to Uni Basel Research Database: Journal article |
Related URLs: | |
Identification Number: |
|
Last Modified: | 01 Feb 2013 08:46 |
Deposited On: | 01 Feb 2013 08:41 |
Repository Staff Only: item control page