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Title: | Design, synthesis and activity as acid ceramidase inhibitors of 2-oxooctanoyl and N- oleoylethanolamine analogues |
Authors: | Grijalvo, Santiago CSIC ORCID; Bedia, Carmen CSIC ORCID CVN; Triola Guillem, Gemma CSIC ORCID; Casas, Josefina ; Llebaria, Amadeu CSIC ORCID; Teixidó, Jordi; Rabal, Obdulia; Levade, Thierry; Delgado Cirilo, Antonio; Fabriàs, Gemma CSIC ORCID | Keywords: | Sphingolipids Ceramide Farber disease Ceramidase Inhibitor |
Issue Date: | 7-Aug-2006 | Publisher: | Elsevier | Citation: | Chemistry and Physics of Lipids 144(1): 69-84 (2006) | Abstract: | The synthesis of novel N-acylethanolamines and their use as inhibitors of the aCDase is reported here. The compounds are either 2-oxooctanamides or oleamides of sphingosine analogs featuring a 3-hydroxy-4,5-hexadecenyl tail replaced by ether or thioether moieties. It appears that, within the 2-oxooctanamide family, the C3–OH group of the sphingosine molecule is required for inhibition both in vitro and in cultured cells. Furthermore, although the (E)-4 double bond is not essential for inhibitory activity, the (E) configuration is required, since the analogue with a (Z)-4 unsaturation was not inhibitory. None of the oleamides inhibited the aCDase in vitro. Conversely, with the exception of N-oleoylethanolamine and its analogs with S-decyl and S-hexadecyl substituents, all the synthesized oleamides inhibited the aCDase in cultured cells, although with a relatively low potency. We conclude that novel aCDase inhibitors can evolve from N-acylation of sphingoid bases with electron deficient-acyl groups. In contrast, chemical modification of the N-oleoylsphingosine backbone does not seem to offer an appropriate strategy to obtain aCDase inhibitors. | Description: | 16 pages, 3 figures, 2 schemes.-- PMID: 16942762 [PubMed].-- Printed version published Oct 2006. | Publisher version (URL): | http://dx.doi.org/10.1016/j.chemphyslip.2006.07.001 | URI: | http://hdl.handle.net/10261/12455 | DOI: | 10.1016/j.chemphyslip.2006.07.001 | ISSN: | 0009-3084 |
Appears in Collections: | (IQAC) Artículos |
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