Application Notes:
N,N-Dihexyl-D-erythro-sphingsosine is an unnatural analog of the vital sphingolipid ceramide. Ceramide functions as a
precursor in the synthesis of sphingomyelin, complex glycosphingolipids, and free sphingosine and it exerts numerous
biological effects, including induction of cell maturation, cell cycle arrest, terminal cell differentiation, cell senescence, and
cell death.1 Instead of the normal fatty acid acylated to sphingosine N,N-Dihexyl-D-erythro-sphingsosine contains two hexyl
groups making it a tertiary amine rather than secondary. Ceramide analogs, such as N,N-Dihexyl-D-erythro-sphingsosine, are
able to induce an a increase in ceramide levels in cells, leading to apoptosis, and may be useful in treating certain diseases.2
N-Hexyl-glucosylceramide is a potent inhibitor of glucosylceramidase, the enzyme responsible for cleaving glucose from
glucosylceramide.3
References:
1. N. S. Radin, “Killing tumours by ceramide-induced apoptosis: a critique of available drugs” Biochemical Journal, Vol. 371 pp. 243-256, 2003
2. J. Erickson and N. Radin “N-Hexyl-0-glucosyl sphingosine, an inhibitor of glucosyl ceramide, beta-glucosidase” Journal of Lipid Research, Vol. 14 pp.
133-137, 1973
3. S. Gatt et al. “Synthetic, non-natural sphingolipid analogs inhibit the biosynthesis of cellular sphingolipids, elevate ceramide and induce apoptotic cell
death” Biochimica et Biophysica Acta (BBA) - Molecular and Cell Biology of Lipids, Vol. 1633(3) pp. 161-169, 2003