D-erythro-SphingosineA potent, highly selective PKC inhibitor

D-erythro-Sphingosine (CAS 123-78-4)

D-erythro-Sphingosine | CAS 123-78-4 is rated 5.0 out of 5 by 2.
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Synonym: trans-4-Sphingenine
Application: A potent, highly selective PKC inhibitor
CAS Number: 123-78-4
Purity: ≥97%
Molecular Weight: 299.49
Molecular Formula: C18H37NO2
* Refer to Certificate of Analysis for lot specific data (including water content).
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D-erythro-Sphingosine is the natural isomer of sphingosine and acts as a potent inhibitor of protein kinase C (IC50=1-3 μM), but does not inhibit protein kinase A or myosin light chain kinase, and activates casein kinase II. This compound has been shown to inhibit calmodulin-dependent enzymes, phosphatidate phosphohydrolase, ATPase, phosphocholine cytidylyltransferase (CTP), and phorbol dibutyrate binding in vitro in human platelets. D-erythro-Sphingosine is active in intact cells and has been identified as an endogenous constituent in HL-60 cells, neutrophils, rat liver, rat brain and mouse tissues.
Other activities of D-erythro-sphingosine include inhibition of phosphatidate phosphohydrolase, Na+,K+-ATPase, CTP:phosphocholine cytidylyltransferase, calmodulin-dependent enzymes, binding of factor VII to tissue factor, binding of thyrotropin releasing hormone to its receptor and activation of EGF receptor kinase, phospholipase D and casein kinase II.


References

1. Hannun, Y.A., et al. 1986. J. Biol. Chem. 261: 12604-12609. PMID: 3462188
2. Merrill, A.H., et al. 1986. J. Biol. Chem. 261: 12610-12615. PMID: 3462189
3. Wilson, E., et al. 1986. J. Biol. Chem. 261: 12616-12623. PMID: 3017982
4. Wilson, E., et al. 1988. J. Biol. Chem. 263: 9304-9309. PMID: 3132460
5. Merrill, A.H., et al. 1989. Biochemistry. 28: 3138-3145. PMID: 2742830
6. Sohal, P.S., et al. 1990. J. Biol. Chem. 265: 11746-11750. PMID: 2164014
7. McDonald, O.B., et al. 1991. J. Biol. Chem. 266: 21773-21776. PMID: 1939200

Physical State :
Solid
Derived From :
Synthetic
Solubility :
Soluble in ethanol (25 mg/m warm), DMSO (25 mg/ml warm), methanol, chloroform, and DMF (10 mg/ml). Insoluble in water.
Storage :
Store at -20° C
Melting Point :
148.76° C (Predicted)
Boiling Point :
~445.9° C at 760 mmHg (Predicted)
Density :
~0.9 g/cm3 (Predicted)
Refractive Index :
n20D 1.49 (Predicted)
IC50 :
PKC: IC50 = 2.8 µM; cAMP-dependent protein kinase alpha-catalytic subunit: IC50 = 98 nM (Rattus norvegicus); Sphingosine kinase 1: IC50 = 3.86 µM (human)
pK Values :
pKa: 11.80 (Predicted), pKb: 7.88 (Predicted)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
PubChem CID :
5280335
Merck Index :
14: 8747
MDL Number :
MFCD00036751
EC Number :
204-651-3
Beilstein Registry :
1727294
SMILES :
CCCCCCCCCCCCC/C=C/[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 Good Quality! This was good quality reagent; chemical worked just fine!
Date published: 2019-04-14
Rated 5 out of 5 by from Xu JD; et al Xu JD; et al. (PubMed ID: 25852136) utilized D-erythro-Sphingosine as a biomarker for andrographolide sodium bisulfite induced nephrotoxicity in rats. -SCBT Publication Review
Date published: 2015-02-18
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