title: Asymmetric synthesis and cytotoxic activity of isomeric phytosphingosine derivatives.
abstract: New phytosphingosine analogues have been conceived, synthesised and their cytotoxicity in B16 murine melanoma cells tested. These compounds embed an isomeric substitution pattern resulting from a formal permutation of the C-2 and C-4 substituents along the aliphatic skeleton of the original sphingoid base. Five different stereoisomers have been accessed through regio- and stereocontrolled opening of the oxirane of long chain epoxyamine precursors. The corresponding N-hexyl and N-octanoyl derivatives have also been prepared. In cell viability experiments all the primary amines were found to be more active than the natural phytosphingosine with IC(50) in the low μM range for the most potent compounds.
authors: LSPCMIB, UMR 5068, CNRS-Université Paul Sabatier-Toulouse III, Toulouse, France.
authors: Arnaud
authors: A
authors: Rives
authors: Cécile
authors: C
authors: Baudoin-Dehoux
authors: Nathalie
authors: N
authors: Saffon
authors: Nathalie
authors: N
authors: Andrieu-Abadie
authors: Yves
authors: Y
authors: Génisson
mesh_terms: D000818:Animals; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D006868:Hydrolysis; D051379:Mice; D008958:Models, Molecular; D015394:Molecular Structure; D013110:Sphingosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D013237:Stereoisomerism
chemical_list: C012491:phytosphingosine; D013110:Sphingosine