Date published: 2025-12-1

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DL-threo-Dihydrosphingosine (CAS 73938-69-9)

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Alternate Names:
DL-threo-1,3-Dihydroxy-2-aminooctadecane
Application:
DL-threo-Dihydrosphingosine is a potent inhibitor of sphingosine kinase activity
CAS Number:
73938-69-9
Purity:
98%
Molecular Weight:
301.51
Molecular Formula:
C18H39NO2
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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DL-threo-Dihydrosphingosine is an inhibitor of Sphk (sphingosine kinase). This inhibitory activity has been employed as a tool for identifying the activity of sphingosine kinase in various processes. A role of sphingosine-1-phosphate generated by sphingosine kinase is suggested in the mobilization of Ca2+ stimulated by local discrete increases in intracellular Ca2+ at m2 and m3 muscarinic acetylcholine receptors. DL-threo-Dihydrosphingosine demonstrates inhibition of Ca2+ mobilization, and modulation of this process is suggested to function as an amplification for Ca2+ signals mediated by sphingosine kinase activity. The extracellular signal-regulated kinase (ERK) pathway is inhibited by DL-threo-Dihydrosphingosine, suggesting participation of sphingosine kinase in this pathway. DL-threo-Dihydrosphingosine was demonstrated to increase the sensitivity of HEK-293 cells to fumonisin B1cytotoxicity, indicating that fumonisin B1 resistance in HEK-293 cells involves rapid formation of sphingosine-1-phosphate by sphingosine kinase which confers survival properties to the cells.


DL-threo-Dihydrosphingosine (CAS 73938-69-9) References

  1. Extracellular sphingomyelinase induces interleukin-6 synthesis in osteoblasts.  |  Tokuda, H., et al. 1999. J Cell Biochem. 72: 262-8. PMID: 10022508
  2. Sphingosine kinase-mediated calcium signaling by muscarinic acetylcholine receptors.  |  van Koppen, CJ., et al. 2001. Life Sci. 68: 2535-40. PMID: 11392623
  3. The roles of sphingosine-1-phosphate in asthma.  |  Jolly, PS., et al. 2002. Mol Immunol. 38: 1239-45. PMID: 12217390
  4. Inhibition of sphingosine kinase in vitro and in platelets. Implications for signal transduction pathways.  |  Buehrer, BM. and Bell, RM. 1992. J Biol Chem. 267: 3154-9. PMID: 1310683
  5. Cycloserine and threo-dihydrosphingosine inhibit TNF-alpha-induced cytotoxicity: evidence for the importance of de novo ceramide synthesis in TNF-alpha signaling.  |  Meyer, SG. and de Groot, H. 2003. Biochim Biophys Acta. 1643: 1-4. PMID: 14654222
  6. Sphingosine kinase activity confers resistance to apoptosis by fumonisin B1 in human embryonic kidney (HEK-293) cells.  |  Sharma, N., et al. 2004. Chem Biol Interact. 151: 33-42. PMID: 15607760
  7. Sphingosine-1-phosphate is a key regulator of proliferation and differentiation in retina photoreceptors.  |  Miranda, GE., et al. 2009. Invest Ophthalmol Vis Sci. 50: 4416-28. PMID: 19357361
  8. Sphingosine-1-phosphate modulates vascular permeability and cell recruitment in acute inflammation in vivo.  |  Roviezzo, F., et al. 2011. J Pharmacol Exp Ther. 337: 830-7. PMID: 21421740
  9. ELOVL6 deficiency aggravates allergic airway inflammation through the ceramide-S1P pathway in mice.  |  Yoshida, K., et al. 2023. J Allergy Clin Immunol. 151: 1067-1080.e9. PMID: 36592705
  10. Sphingosine-mediated phosphatidylinositol metabolism and calcium mobilization.  |  Chao, CP., et al. 1994. J Biol Chem. 269: 5849-56. PMID: 8119927
  11. The identification of DL-threo dihydrosphingosine and sphingosine as novel inhibitors of extracellular signal-regulated kinase signalling in airway smooth muscle.  |  Tolan, D., et al. 1996. Br J Pharmacol. 119: 185-6. PMID: 8886394
  12. Sphingosine kinase-mediated Ca2+ signalling by G-protein-coupled receptors.  |  Meyer zu Heringdorf, D., et al. 1998. EMBO J. 17: 2830-7. PMID: 9582276
  13. Sphingosine modulates interleukin-6 synthesis in osteoblasts.  |  Kozawa, O., et al. 1998. J Cell Biochem. 70: 338-45. PMID: 9706871

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

DL-threo-Dihydrosphingosine, 10 mg

sc-201389
10 mg
$190.00