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Chemical Compound Review

SAFINGOL     2-aminooctadecane-1,3-diol

Synonyms: AG-J-99105, CHEBI:46968, D6783_SIGMA, KB-64478, CTK4C9052, ...
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Disease relevance of Dihydrosphingosine

  • A Bacillus subtilis mutant spnA95 was isolated as resistant at 30 degrees C to the protein kinase C (PKC) inhibitor, sphinganine, and temperature sensitive for growth [1].
  • Priming was not altered by pertussis toxin or intracellular calcium chelation, but the PAF receptor antagonist WEB 2086 and the protein kinase C (PKC) inhibitors sphinganine and staurosporine significantly inhibited the primed response [2].
  • Our previous work has shown that a number of sphingolipid metabolites including sphingosine, sphinganine, and other long-chain bases potently induced apoptosis in human hepatoma cells [3].
  • The results show that the traditional method reduced the total fumonisins in tortillas and reduced the sphinganine elevation (a biomarker closely correlated with fumonisin toxicity) in cells treated with extracts of tortillas compared with cells treated with extracts of contaminated maize [4].
  • Washed cells of Bacteroides melaninogenicus are unable to incorporate the sphingolipid precursor 3-ketodihydrosphingosine (3KDS) or dihydrosphingosine into the complete sphingolipids ceramide phosphorylethanolamine (CPE) and ceramide phosphorylglycerol (CPG), whereas growing cultures are able to do so [5].

High impact information on Dihydrosphingosine


Chemical compound and disease context of Dihydrosphingosine


Biological context of Dihydrosphingosine

  • We now report that another PKC inhibitor, sphinganine, also inhibits the effect of TPA on action potential height and calcium current in cultured bag cell neurons, and that N-acetylsphinganine, an inactive sphinganine analog, fails to inhibit the effects of PKC activators [15].
  • Consistently, reduction of free sphinganine levels stimulates cell polarity development [16].
  • In addition, there was no effect of sphinganine on cell viability in this concentration range [17].
  • They stimulated PMN to increase the availability of PDB binding sites by a sphinganine-sensitive mechanism, but their actions differed from those of ionophores [18].
  • After 24 h, low concentrations of sphinganine (1-5 microM blocked both cell adherence and the inhibition of growth in response to phorbol 12-myristate 13-acetate, as measured by cell number and acid phosphatase activity [19].

Anatomical context of Dihydrosphingosine


Associations of Dihydrosphingosine with other chemical compounds


Gene context of Dihydrosphingosine


Analytical, diagnostic and therapeutic context of Dihydrosphingosine


  1. A mutant cysteinyl-tRNA synthetase affecting timing of chromosomal replication initiation in B. subtilis and conferring resistance to a protein kinase C inhibitor. Séror, S.J., Casarégola, S., Vannier, F., Zouari, N., Dahl, M., Boye, E. EMBO J. (1994) [Pubmed]
  2. Mechanism and regulation of neutrophil priming by platelet-activating factor. Gay, J.C. J. Cell. Physiol. (1993) [Pubmed]
  3. Role of AKT kinase in sphingosine-induced apoptosis in human hepatoma cells. Chang, H.C., Tsai, L.H., Chuang, L.Y., Hung, W.C. J. Cell. Physiol. (2001) [Pubmed]
  4. Total fumonisins are reduced in tortillas using the traditional nixtamalization method of mayan communities. Palencia, E., Torres, O., Hagler, W., Meredith, F.I., Williams, L.D., Riley, R.T. J. Nutr. (2003) [Pubmed]
  5. Energy-dependent incorporation of sphingolipid precursors and fatty acids in Bacteriodes melaninogenicus. Lev, M., Milford, A.F. J. Bacteriol. (1977) [Pubmed]
  6. Alteration of the 4-sphingenine scaffolds of ceramides in keratinocyte-specific Arnt-deficient mice affects skin barrier function. Takagi, S., Tojo, H., Tomita, S., Sano, S., Itami, S., Hara, M., Inoue, S., Horie, K., Kondoh, G., Hosokawa, K., Gonzalez, F.J., Takeda, J. J. Clin. Invest. (2003) [Pubmed]
  7. gamma-Tocopherol or combinations of vitamin E forms induce cell death in human prostate cancer cells by interrupting sphingolipid synthesis. Jiang, Q., Wong, J., Fyrst, H., Saba, J.D., Ames, B.N. Proc. Natl. Acad. Sci. U.S.A. (2004) [Pubmed]
  8. Fumonisins and Alternaria alternata lycopersici toxins: sphinganine analog mycotoxins induce apoptosis in monkey kidney cells. Wang, W., Jones, C., Ciacci-Zanella, J., Holt, T., Gilchrist, D.G., Dickman, M.B. Proc. Natl. Acad. Sci. U.S.A. (1996) [Pubmed]
  9. 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]
  10. Activation of caspase-3-like proteases in apoptosis induced by sphingosine and other long-chain bases in Hep3B hepatoma cells. Hung, W.C., Chang, H.C., Chuang, L.Y. Biochem. J. (1999) [Pubmed]
  11. The effect of repeated gavage doses of fumonisin B1 on the sphinganine and sphingosine levels in vervet monkeys. van der Westhuizen, L., Shephard, G.S., van Schalkwyk, D.J. Toxicon (2001) [Pubmed]
  12. Metabolism and neurite promoting effect of exogenous sphingosylphosphocholine in cultured murine neuroblastoma cells. Sugiyama, E., Uemura, K., Hara, A., Taketomi, T. J. Biochem. (1993) [Pubmed]
  13. Type C Niemann-Pick disease: a murine model of the lysosomal cholesterol lipidosis accumulates sphingosine and sphinganine in liver. Goldin, E., Roff, C.F., Miller, S.P., Rodriguez-Lafrasse, C., Vanier, M.T., Brady, R.O., Pentchev, P.G. Biochim. Biophys. Acta (1992) [Pubmed]
  14. Sphingolipid metabolism in Bacteroideaceae. Stoffel, W., Dittmar, K., Wilmes, R. Hoppe-Seyler's Z. Physiol. Chem. (1975) [Pubmed]
  15. Inhibitors of protein kinase C prevent enhancement of calcium current and action potentials in peptidergic neurons of Aplysia. Conn, P.J., Strong, J.A., Kaczmarek, L.K. J. Neurosci. (1989) [Pubmed]
  16. Polarized membrane traffic and cell polarity development is dependent on dihydroceramide synthase-regulated sphinganine turnover. Van IJzendoorn, S.C., Van Der Wouden, J.M., Liebisch, G., Schmitz, G., Hoekstra, D. Mol. Biol. Cell (2004) [Pubmed]
  17. Sphinganine effects on chemoattractant-induced diacylglycerol generation, calcium fluxes, superoxide production, and on cell viability in the human neutrophil. Delivery of sphinganine with bovine serum albumin minimizes cytotoxicity without affecting inhibition of the respiratory burst. Lambeth, J.D., Burnham, D.N., Tyagi, S.R. J. Biol. Chem. (1988) [Pubmed]
  18. Translocation of protein kinase C in human polymorphonuclear neutrophils. Regulation by cytosolic Ca2(+)-independent and Ca2(+)-dependent mechanisms. O'Flaherty, J.T., Jacobson, D.P., Redman, J.F., Rossi, A.G. J. Biol. Chem. (1990) [Pubmed]
  19. Inhibition of phorbol ester-dependent differentiation of human promyelocytic leukemic (HL-60) cells by sphinganine and other long-chain bases. Merrill, A.H., Sereni, A.M., Stevens, V.L., Hannun, Y.A., Bell, R.M., Kinkade, J.M. J. Biol. Chem. (1986) [Pubmed]
  20. Differential effects of long-chain (sphingoid) bases on the monocytic differentiation of human leukemia (HL-60) cells induced by phorbol esters, 1 alpha, 25-dihydroxyvitamin D3, or ganglioside GM3. Stevens, V.L., Winton, E.F., Smith, E.E., Owens, N.E., Kinkade, J.M., Merrill, A.H. Cancer Res. (1989) [Pubmed]
  21. Nonselective inhibition of neutrophil functions by sphinganine. Pittet, D., Krause, K.H., Wollheim, C.B., Bruzzone, R., Lew, D.P. J. Biol. Chem. (1987) [Pubmed]
  22. Utilization of exogenously supplied sphingosine analogues for sphingolipid biosynthesis in Chinese hamster ovary and mouse LM cell fibroblasts. Ladenson, R.C., Monsey, J.D., Allin, J., Silbert, D.F. J. Biol. Chem. (1993) [Pubmed]
  23. Fumonisin B1 inhibits sphingosine (sphinganine) N-acyltransferase and de novo sphingolipid biosynthesis in cultured neurons in situ. Merrill, A.H., van Echten, G., Wang, E., Sandhoff, K. J. Biol. Chem. (1993) [Pubmed]
  24. Bimodal regulation of ceramidase by interleukin-1beta. Implications for the regulation of cytochrome p450 2C11. Nikolova-Karakashian, M., Morgan, E.T., Alexander, C., Liotta, D.C., Merrill, A.H. J. Biol. Chem. (1997) [Pubmed]
  25. Acylation of naturally occurring and synthetic 1-deoxysphinganines by ceramide synthase. Formation of N-palmitoyl-aminopentol produces a toxic metabolite of hydrolyzed fumonisin, AP1, and a new category of ceramide synthase inhibitor. Humpf, H.U., Schmelz, E.M., Meredith, F.I., Vesper, H., Vales, T.R., Wang, E., Menaldino, D.S., Liotta, D.C., Merrill, A.H. J. Biol. Chem. (1998) [Pubmed]
  26. Role of ceramide in mitogenesis induced by exogenous sphingoid bases. Hauser, J.M., Buehrer, B.M., Bell, R.M. J. Biol. Chem. (1994) [Pubmed]
  27. 1,25-Dihydroxyvitamin D3 regulation of c-myc protooncogene transcription. Possible involvement of protein kinase C. Simpson, R.U., Hsu, T., Wendt, M.D., Taylor, J.M. J. Biol. Chem. (1989) [Pubmed]
  28. Sphingolipids are required for the stable membrane association of glycosylphosphatidylinositol-anchored proteins in yeast. Watanabe, R., Funato, K., Venkataraman, K., Futerman, A.H., Riezman, H. J. Biol. Chem. (2002) [Pubmed]
  29. A snc1 endocytosis mutant: phenotypic analysis and suppression by overproduction of dihydrosphingosine phosphate lyase. Grote, E., Vlacich, G., Pypaert, M., Novick, P.J. Mol. Biol. Cell (2000) [Pubmed]
  30. Cloning and characterization of a Saccharomyces cerevisiae alkaline ceramidase with specificity for dihydroceramide. Mao, C., Xu, R., Bielawska, A., Szulc, Z.M., Obeid, L.M. J. Biol. Chem. (2000) [Pubmed]
  31. Tsc3p is an 80-amino acid protein associated with serine palmitoyltransferase and required for optimal enzyme activity. Gable, K., Slife, H., Bacikova, D., Monaghan, E., Dunn, T.M. J. Biol. Chem. (2000) [Pubmed]
  32. Accumulation of phosphorylated sphingoid long chain bases results in cell growth inhibition in Saccharomyces cerevisiae. Kim, S., Fyrst, H., Saba, J. Genetics (2000) [Pubmed]
  33. Sphinganine causes early activation of JNK and p38 MAPK and inhibition of AKT activation in HT-29 human colon cancer cells. Ahn, E.H., Schroeder, J.J. Anticancer Res. (2006) [Pubmed]
  34. Quantification of sphingosine and sphinganine from crude lipid extracts by HPLC electrospray ionization tandem mass spectrometry. Lieser, B., Liebisch, G., Drobnik, W., Schmitz, G. J. Lipid Res. (2003) [Pubmed]
  35. Quantitative analysis of ceramide molecular species by high performance liquid chromatography. Yano, M., Kishida, E., Muneyuki, Y., Masuzawa, Y. J. Lipid Res. (1998) [Pubmed]
  36. A cross-sectional study of human serum sphingolipids, diet and physiologic parameters. Abnet, C.C., Borkowf, C.B., Qiao, Y.L., Albert, P.S., Wang, E., Merrill, A.H., Mark, S.D., Dong, Z.W., Taylor, P.R., Dawsey, S.M. J. Nutr. (2001) [Pubmed]
  37. SPC-100270, a protein kinase C inhibitor, reduced hypoxic injury due to reperfusion following orthotopic liver transplantation in the rat. Thurman, R.G., Gao, W., Connor, H.D., Mason, R.P., Lemasters, J.J., Bozigian, H., Adams, L.M. Transpl. Int. (1994) [Pubmed]
  38. Tissue sphinganine as a biomarker of fumonisin-induced apoptosis. Delongchamp, R.R., Young, J.F. Food additives and contaminants. (2001) [Pubmed]
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