Replaces Prod. #: ALX-306-009
Potent and specific inhibitor of sphingosine kinase (IC50=5µM) which blocks conversion of sphingosine to sphingosine-1-phosphate (Prod. No. BML-SL140). Inhibitor of protein kinase C (PKC) which also stimulates Src-kinase. May affect expression of cell surface selectins, which in turn mediate leukocyte or tumor cell adhesion to endothelial cells and platelets. Induces apoptosis. Stereospecifically induces EGF receptor autophosphorylation producing EGF-like activity in vitro in the absence of EGF. Produced endogenously via ceramide catabolism. May be a target for neuropathic pain therapy.
Product Details
| Alternative Name: | N,N-Dimethyl-D-erythro-sphingosine |
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| Formula: | C20H41NO2 |
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| MW: | 327.6 |
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| Source: | Synthetic. |
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| CAS: | 119567-63-4 |
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| Purity: | ≥98% (TLC) |
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| Appearance: | White to off-white waxy solid or viscous oil. |
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| Solubility: | Soluble in DMSO (25mg/ml) or 100% ethanol (25mg/ml). |
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| Shipping: | Ambient Temperature |
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| Long Term Storage: | -20°C |
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| Use/Stability: | Stable for at least 1 year after receipt when stored at -20°C. Stock solutions are stable for up to 3 months at -20°C. |
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| Technical Info/Product Notes: | Note: Product is not sterile |
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| Regulatory Status: | RUO - Research Use Only |
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Product Literature References
Metabolomics implicates altered sphingolipids in chronic pain of neuropathic origin: G.J. Patti, et al.; Nat. Chem. Biol.
8, 232 (2012),
Abstract;
D-erythro-N,N-dimethylsphingosine inhibits bFGF-induced proliferation of cerebral, aortic and coronary smooth muscle cells: C.B. Xu, et al.; Atherosclerosis
164, 237 (2002),
Abstract;
N,N-Dimethylsphingosine is a potent competitive inhibitor of sphingosine kinase but not of protein kinase C: modulation of cellular levels of sphingosine 1-phosphate and ceramide: L.C. Edsall, et al.; Biochemistry
37, 12892 (1998),
Abstract;
N,N-dimethylsphingosine inhibition of sphingosine kinase and sphingosine 1-phosphate activity in human platelets: Y. Yatomi, et al.; Biochemistry
35, 626 (1996),
Abstract;
Sphingosine and its methylated derivative N,N-dimethylsphingosine (DMS) induce apoptosis in a variety of human cancer cell lines: E.A. Sweeney, et al.; Int. J. Cancer
66, 358 (1996),
Abstract;
Induction of apoptosis by sphingosine in human leukemic HL-60 cells: a possible endogenous modulator of apoptotic DNA fragmentation occurring during phorbol ester-induced differentiation: H. Ohta, et al.; Cancer Res.
55, 691 (1995),
Abstract;
Effect of sphingosine and its N-methyl derivatives on oxidative burst, phagokinetic activity, and trans-endothelial migration of human neutrophils: S. Kimura, et al.; Biochem. Pharmacol.
44, 1585 (1992),
Abstract;
Downregulation of GMP-140 (CD62 or PADGEM) expression on platelets by N,N-dimethyl and N,N,N-trimethyl derivatives of sphingosine: K. Handa, et al.; Biochemistry
30, 11682 (1991),
Abstract;
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: Y. Igarashi, et al.; J. Biol. Chem.
265, 5385 (1990),
Abstract;
Full Text
Effect of chemically well-defined sphingosine and its N-methyl derivatives on protein kinase C and src kinase activities: Y. Igarashi, et al.; Biochemistry
28, 6796 (1989),
Abstract;
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