Molecular structure of D-erythro-N,N-Dimethylsphingosine, CAS Number: 119567-63-4
D-erythro-N,N-Dimethylsphingosine (CAS 119567-63-4)
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Alternate Names:
DMS, SK Inhibitor III, Sphingosine Kinase Inhibitor III
Application:
D-erythro-N,N-Dimethylsphingosine is a sphingosine kinase inhibitor
CAS Number:
119567-63-4
Purity:
≥98%
Molecular Weight:
327.5
Molecular Formula:
C20H41NO2
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.
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SDS & Certificate of Analysis
D-erythro-N,N-Dimethylsphingosine inhibits SphK (sphingosine kinase), blocking the conversion of sphingosine to sphingosine-1 phosphate. It is an endogenous compound produced via ceramide catabolism. D-erythro-N,N-Dimethylsphingosine is capable of producing EGF-like activity in vitro without the presence of any EFG-2 by stereospecifically inducing EGF receptor autophosphorylation. D-erythro-N,N-Dimethylsphingosine may act to inhibit PKC (protein kinase C), enhance src-kinase activity, and induce apoptosis.
D-erythro-N,N-Dimethylsphingosine (CAS 119567-63-4) References
- D-erythro-N,N-dimethylsphingosine inhibits bFGF-induced proliferation of cerebral, aortic and coronary smooth muscle cells. | Xu, CB., et al. 2002. Atherosclerosis. 164: 237-43. PMID: 12204793
- Suppression of osteoclastogenesis by N,N-dimethyl-D-erythro-sphingosine: a sphingosine kinase inhibition-independent action. | Kim, HJ., et al. 2007. Mol Pharmacol. 72: 418-28. PMID: 17504945
- N, N-dimethyl-D-erythro-sphingosine increases intracellular Ca2+ concentration via Na+-Ca2+-exchanger in HCT116 human colon cancer cells. | Kim, HL. and Im, DS. 2008. Arch Pharm Res. 31: 54-9. PMID: 18277608
- N-(4-Hydroxyphenyl)retinamide increases dihydroceramide and synergizes with dimethylsphingosine to enhance cancer cell killing. | Wang, H., et al. 2008. Mol Cancer Ther. 7: 2967-76. PMID: 18790777
- The sphingosine kinase inhibitor N,N-dimethylsphingosine inhibits neointimal hyperplasia. | McDonald, RA., et al. 2010. Br J Pharmacol. 159: 543-53. PMID: 20015089
- Inhibition of MAP kinase by sphingosine and its methylated derivative, N,N-dimethylsphingosine. | Sakakura, C., et al. 1997. Int J Oncol. 11: 31-9. PMID: 21528177
- A ceramide analogue inhibits T cell proliferative response through inhibition of glycosphingolipid synthesis and enhancement of N,N-dimethylsphingosine synthesis. | Felding-Habermann, B., et al. 1990. Biochemistry. 29: 6314-22. PMID: 2207076
- 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., et al. 1990. J Biol Chem. 265: 5385-9. PMID: 2318819
- Effect of chemically well-defined sphingosine and its N-methyl derivatives on protein kinase C and src kinase activities. | Igarashi, Y., et al. 1989. Biochemistry. 28: 6796-800. PMID: 2479412
- N,N-dimethylsphingosine attenuates myocardial ischemia-reperfusion injury by recruiting regulatory T cells through PI3K/Akt pathway in mice. | Fang, J., et al. 2016. Basic Res Cardiol. 111: 32. PMID: 27048490
- Sphingoid Bases Regulate the Sigma-1 Receptor-Sphingosine and N,N'-Dimethylsphingosine Are Endogenous Agonists. | Li, J., et al. 2023. Int J Mol Sci. 24: PMID: 36834510
- Determination of the pKa of membrane-bound N,N-dimethylsphingosine using deuterium NMR spectroscopy. | Lau, B. and Macdonald, PM. 1995. Biochim Biophys Acta. 1237: 37-42. PMID: 7619840
- In vitro and in vivo induction of apoptosis by sphingosine and N, N-dimethylsphingosine in human epidermoid carcinoma KB-3-1 and its multidrug-resistant cells. | Shirahama, T., et al. 1997. Clin Cancer Res. 3: 257-64. PMID: 9815681
Inhibitor of:
PKC, Ser/Thr Protein Kinase, SK1, SphK, and SphK2.Activator of:
GD3 Synthase.Ordering Information
| Product Name | Catalog # | UNIT | Price | Qty | FAVORITES | |
D-erythro-N,N-Dimethylsphingosine, 5 mg | sc-201373 | 5 mg | $81.00 | |||
D-erythro-N,N-Dimethylsphingosine, 25 mg | sc-201373A | 25 mg | $316.00 |