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Chemical Compound Review

FT-0624522     (E,2R,3R)-2-aminooctadec-4- ene-1,3-diol

Synonyms: AC1L9L4S, I14-103018, 6036-85-7, SPH, UNII-4423HD881O, ...
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Disease relevance of sphingosine


Psychiatry related information on sphingosine

  • As one sphingolipid metabolite, sphingosine is known to exert a potent antimicrobial effect on S. aureus at physiologic levels, and it may play a significant role in bacterial defense mechanisms of healthy normal skin [6].

High impact information on sphingosine


Chemical compound and disease context of sphingosine


Biological context of sphingosine

  • It appears that sphingosine affects TNF alpha-induced PGE2 production via a mechanism that is independent of PKC involvement, and that sphingosine may function as an endogenous second messenger capable of modulating the responsiveness of the cell to external stimuli [16].
  • Down-regulation of PKC by overnight incubation of cells with PMA or inhibition of PKC with the PKC inhibitor sphingosine blocked the stimulation of MAP kinase by epinephrine and, correspondingly, epinephrine-promoted AA release was inhibited under these conditions [17].
  • The capacity of drugs that act on type 1 sphingosine 1-phosphate receptors to suppress organ graft rejection in humans and autoimmunity in animal models without apparent impairment of host defenses against infections suggests that this system is a promising target for new forms of immunotherapy [18].
  • Transfection-mediated upregulation of p27kip1 decreases sphingosine-induced cell death in alpha-catenin-deficient cells [19].
  • Adding TPA (100 nM) before insemination caused a reduction in the frequency of HRs at fertilization, but neither TPA nor sphingosine affected the frequency or size of HRs when they were added after the start of fertilization [20].

Anatomical context of sphingosine


Associations of sphingosine with other chemical compounds


Gene context of sphingosine


Analytical, diagnostic and therapeutic context of sphingosine


  1. The sphingosine kinase-sphingosine-1-phosphate axis is a determinant of mast cell function and anaphylaxis. Olivera, A., Mizugishi, K., Tikhonova, A., Ciaccia, L., Odom, S., Proia, R.L., Rivera, J. Immunity (2007) [Pubmed]
  2. The clinical implication and molecular mechanism of preferential IL-4 production by modified glycolipid-stimulated NKT cells. Oki, S., Chiba, A., Yamamura, T., Miyake, S. J. Clin. Invest. (2004) [Pubmed]
  3. Sorting of sphingolipids in the endocytic pathway of HT29 cells. Kok, J.W., Babia, T., Hoekstra, D. J. Cell Biol. (1991) [Pubmed]
  4. Serum and depolarizing agents cause acute neurotoxicity in cultured cerebellar granule cells: role of the glutamate receptor responsive to N-methyl-D-aspartate. Schramm, M., Eimerl, S., Costa, E. Proc. Natl. Acad. Sci. U.S.A. (1990) [Pubmed]
  5. Gaucher disease types 1, 2, and 3: differential mutations of the acid beta-glucosidase active site identified with conduritol B epoxide derivatives and sphingosine. Grabowski, G.A., Dinur, T., Osiecki, K.M., Kruse, J.R., Legler, G., Gatt, S. Am. J. Hum. Genet. (1985) [Pubmed]
  6. Decreased levels of sphingosine, a natural antimicrobial agent, may be associated with vulnerability of the stratum corneum from patients with atopic dermatitis to colonization by Staphylococcus aureus. Arikawa, J., Ishibashi, M., Kawashima, M., Takagi, Y., Ichikawa, Y., Imokawa, G. J. Invest. Dermatol. (2002) [Pubmed]
  7. Calcium mobilization via sphingosine kinase in signalling by the Fc epsilon RI antigen receptor. Choi, O.H., Kim, J.H., Kinet, J.P. Nature (1996) [Pubmed]
  8. Functions of sphingolipids and sphingolipid breakdown products in cellular regulation. Hannun, Y.A., Bell, R.M. Science (1989) [Pubmed]
  9. A vital stain for the Golgi apparatus. Lipsky, N.G., Pagano, R.E. Science (1985) [Pubmed]
  10. Knockout of Arabidopsis accelerated-cell-death11 encoding a sphingosine transfer protein causes activation of programmed cell death and defense. Brodersen, P., Petersen, M., Pike, H.M., Olszak, B., Skov, S., Odum, N., Jørgensen, L.B., Brown, R.E., Mundy, J. Genes Dev. (2002) [Pubmed]
  11. Sphingosine enhances apoptosis of radiation-resistant prostate cancer cells. Nava, V.E., Cuvillier, O., Edsall, L.C., Kimura, K., Milstien, S., Gelmann, E.P., Spiegel, S. Cancer Res. (2000) [Pubmed]
  12. Sphingosine-induced apoptosis in rhabdomyosarcoma cell lines is dependent on pre-mitochondrial Bax activation and post-mitochondrial caspases. Phillips, D.C., Martin, S., Doyle, B.T., Houghton, J.A. Cancer Res. (2007) [Pubmed]
  13. Clostridium perfringens alpha-toxin activates the sphingomyelin metabolism system in sheep erythrocytes. Ochi, S., Oda, M., Matsuda, H., Ikari, S., Sakurai, J. J. Biol. Chem. (2004) [Pubmed]
  14. Sphingosine kinase 2 is required for modulation of lymphocyte traffic by FTY720. Kharel, Y., Lee, S., Snyder, A.H., Sheasley-O'neill, S.L., Morris, M.A., Setiady, Y., Zhu, R., Zigler, M.A., Burcin, T.L., Ley, K., Tung, K.S., Engelhard, V.H., Macdonald, T.L., Pearson-White, S., Lynch, K.R. J. Biol. Chem. (2005) [Pubmed]
  15. A specific enhancing effect of N,N-dimethylsphingosine on epidermal growth factor receptor autophosphorylation. Demonstration of its endogenous occurrence (and the virtual absence of unsubstituted sphingosine) in human epidermoid carcinoma A431 cells. Igarashi, Y., Kitamura, K., Toyokuni, T., Dean, B., Fenderson, B., Ogawass, T., Hakomori, S. J. Biol. Chem. (1990) [Pubmed]
  16. Sphingosine synergistically stimulates tumor necrosis factor alpha-induced prostaglandin E2 production in human fibroblasts. Candela, M., Barker, S.C., Ballou, L.R. J. Exp. Med. (1991) [Pubmed]
  17. Protein kinase C-dependent activation of cytosolic phospholipase A2 and mitogen-activated protein kinase by alpha 1-adrenergic receptors in Madin-Darby canine kidney cells. Xing, M., Insel, P.A. J. Clin. Invest. (1996) [Pubmed]
  18. Regulation of immunity by lysosphingolipids and their G protein-coupled receptors. Goetzl, E.J., Rosen, H. J. Clin. Invest. (2004) [Pubmed]
  19. Expression of alpha-catenin in alpha-catenin-deficient cells increases resistance to sphingosine-induced apoptosis. Matsubara, S., Ozawa, M. J. Cell Biol. (2001) [Pubmed]
  20. Evidence for an inhibitory effect of protein kinase C on G-protein-mediated repetitive calcium transients in hamster eggs. Swann, K., Igusa, Y., Miyazaki, S. EMBO J. (1989) [Pubmed]
  21. Division of labor: specialization of sphingosine kinases in mast cells. Beaven, M.A. Immunity (2007) [Pubmed]
  22. Sphingosine 1-phosphate type 1 receptor agonism inhibits transendothelial migration of medullary T cells to lymphatic sinuses. Wei, S.H., Rosen, H., Matheu, M.P., Sanna, M.G., Wang, S.K., Jo, E., Wong, C.H., Parker, I., Cahalan, M.D. Nat. Immunol. (2005) [Pubmed]
  23. Sphingosine 1-phosphate promotes endothelial cell barrier integrity by Edg-dependent cytoskeletal rearrangement. Garcia, J.G., Liu, F., Verin, A.D., Birukova, A., Dechert, M.A., Gerthoffer, W.T., Bamberg, J.R., English, D. J. Clin. Invest. (2001) [Pubmed]
  24. Protein kinase C is involved in laminin stimulation of neurite outgrowth. Bixby, J.L. Neuron (1989) [Pubmed]
  25. Another activation switch for endothelial nitric oxide synthase: why does it have to be so complicated? Marletta, M.A. Trends Biochem. Sci. (2001) [Pubmed]
  26. FTY720: targeting G-protein-coupled receptors for sphingosine 1-phosphate in transplantation and autoimmunity. Brinkmann, V., Lynch, K.R. Curr. Opin. Immunol. (2002) [Pubmed]
  27. Phosphorylation-dependent translocation of sphingosine kinase to the plasma membrane drives its oncogenic signalling. Pitson, S.M., Xia, P., Leclercq, T.M., Moretti, P.A., Zebol, J.R., Lynn, H.E., Wattenberg, B.W., Vadas, M.A. J. Exp. Med. (2005) [Pubmed]
  28. Sphingosine blocks human polymorphonuclear leukocyte phagocytosis through inhibition of mitogen-activated protein kinase activation. Raeder, E.M., Mansfield, P.J., Hinkovska-Galcheva, V., Kjeldsen, L., Shayman, J.A., Boxer, L.A. Blood (1999) [Pubmed]
  29. Mice deficient in sphingosine kinase 1 are rendered lymphopenic by FTY720. Allende, M.L., Sasaki, T., Kawai, H., Olivera, A., Mi, Y., van Echten-Deckert, G., Hajdu, R., Rosenbach, M., Keohane, C.A., Mandala, S., Spiegel, S., Proia, R.L. J. Biol. Chem. (2004) [Pubmed]
  30. Differential phospholipase D activation by bradykinin and sphingosine 1-phosphate in NIH 3T3 fibroblasts overexpressing gelsolin. Banno, Y., Fujita, H., Ono, Y., Nakashima, S., Ito, Y., Kuzumaki, N., Nozawa, Y. J. Biol. Chem. (1999) [Pubmed]
  31. Involvement of sphingosine kinase in TNF-alpha-stimulated tetrahydrobiopterin biosynthesis in C6 glioma cells. Vann, L.R., Payne, S.G., Edsall, L.C., Twitty, S., Spiegel, S., Milstien, S. J. Biol. Chem. (2002) [Pubmed]
  32. Sphingosine-1-phosphate rapidly induces Rho-dependent neurite retraction: action through a specific cell surface receptor. Postma, F.R., Jalink, K., Hengeveld, T., Moolenaar, W.H. EMBO J. (1996) [Pubmed]
  33. The subcellular organization of Madin-Darby canine kidney cells during the formation of a polarized epithelium. Bacallao, R., Antony, C., Dotti, C., Karsenti, E., Stelzer, E.H., Simons, K. J. Cell Biol. (1989) [Pubmed]
  34. Ceramide stimulates epidermal growth factor receptor phosphorylation in A431 human epidermoid carcinoma cells. Evidence that ceramide may mediate sphingosine action. Goldkorn, T., Dressler, K.A., Muindi, J., Radin, N.S., Mendelsohn, J., Menaldino, D., Liotta, D., Kolesnick, R.N. J. Biol. Chem. (1991) [Pubmed]
  35. Retinoblastoma protein dephosphorylation induced by D-erythro-sphingosine. Chao, R., Khan, W., Hannun, Y.A. J. Biol. Chem. (1992) [Pubmed]
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