| Synthesis of 7-oxasphingosine and -ceramide analogues and their evaluation in a model for apoptosis. | |
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MedLine Citation:
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PMID: 17191816 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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The 7-oxasphingosine (1), 7-oxaceramide (2), the thio-oxaceramide 3, and N-methyloxaceramide 4 were synthesised from D-galactose via the building block 9. The apoptosis-inducing properties of 1-4 were compared to those of sphingosine (Sph) and ceramide (Cer) using a human neuroblastoma (SK-N-BE) and a murine-promyelocyte-derived (32d) cell line. There were no differences between 2-4 and Cer in terms of their effects on the viability of cells and their ability to trigger cell proliferation. However, in the presence of N,N-dimethylsphingosine, an inhibitor of sphingosine kinase (SPHK), Cer was more potent than thio-ceramide 3 in 32d cells, while thio-ceramide 3 was more potent and efficacious in SK-N-BE cells, where it showed an IC50 value of 3 nM compared to 100 nM for Cer. In both SK-N-BE and 32d cells, 7-oxasphingosine (1) and Sph were equally toxic, even in the presence of N,N-dimethylsphingosine. |
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Authors:
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Roshini Rajan; Kurt Wallimann; Andrea Vasella; Deborah Pace; Armando A Genazzani; Pier Luigi Canonico; Fabrizio Condorelli |
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Publication Detail:
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Type: Journal Article |
Journal Detail:
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Title: Chemistry & biodiversity Volume: 1 ISSN: 1612-1880 ISO Abbreviation: Chem. Biodivers. Publication Date: 2004 Nov |
Date Detail:
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Created Date: 2006-12-28 Completed Date: 2007-02-22 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 101197449 Medline TA: Chem Biodivers Country: Switzerland |
Other Details:
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Languages: eng Pagination: 1785-99 Citation Subset: IM |
Affiliation:
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Laboratorium für Organische Chemie, ETH-Hönggerberg, Wolfgang Pauli-Strasse 10, CH-8093 Zürich. |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Animals Apoptosis / drug effects*, physiology Cell Line, Tumor Ceramides / chemical synthesis*, pharmacology Drug Evaluation, Preclinical / methods Humans Mice Sphingosine / analogs & derivatives*, chemical synthesis*, pharmacology |
| Chemical | |
Reg. No./Substance:
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0/Ceramides; 123-78-4/Sphingosine |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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