DL-threo-DihydrosphingosineA potent inhibitor of sphingosine kinase activity

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

DL-threo-Dihydrosphingosine | CAS 73938-69-9 is rated 5.0 out of 5 by 1.
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Synonym: DL-threo-1,3-Dihydroxy-2-aminooctadecane
Application: A potent inhibitor of sphingosine kinase activity
CAS Number: 73938-69-9
Purity: 98%
Molecular Weight: 301.51
Molecular Formula: C18H39NO2
* Refer to Certificate of Analysis for lot specific data (including water content).
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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.


References

1. Tolan, D., et al. 1996. Br. J. Pharmacol. 119: 185-186. PMID: 8886394
2. Meyer zu Heringdorf, D., et al. 1998. EMBO J. 17: 2830-2837. PMID: 9582276
3. van Koppen, C.J., et al. 2001. Life Sci. 68: 2535-2540. PMID: 11392623
4. Sharma, N., et al. 2004. Chem. Biol. Interact. 151: 33-42. PMID: 15607760

Physical State :
Solid
Solubility :
Soluble in ethanol (10 mg/ml) at 37° C, DMSO (5 mg/ml, warm), and chloroform.
Storage :
Store at -20° C
Melting Point :
149.06° C (Predicted)
Boiling Point :
~446.2° C at 760 mmHg (Predicted)
Density :
~0.9 g/cm3 (Predicted)
Refractive Index :
n20D 1.48
pK Values :
pKa: 12.57
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
PubChem CID :
3058739
MDL Number :
MFCD00069638
SMILES :
CCCCCCCCCCCCCCC[C@@H]([C@H](CO)N)O

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Certificate of Analysis

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Rated 5 out of 5 by from Sharma et al Sharma et al. (PubMed ID 15607760) found that DL-threo-Dihydrosphingosine increased HEK-293 cell sensitivity to fumonisin B1 via sphingosine kinase inhibition. -SCBT Publication Review
Date published: 2015-06-06
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