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N,N-Dimethylsphingosine, D-erythro

Sphingosine kinase inhibitor
 
BML-SL105-0005 5 mg 72.00 USD
 
BML-SL105-0025 25 mg 287.00 USD
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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 Specification

Alternative Name:N,N-Dimethyl-D-erythro-sphingosine
 
Formula:C20H41NO2
 
MW:327.6
 
Source:Synthetic.
 
CAS:119567-63-4
 
Purity:≥98% (TLC)
 
Appearance:White to off-white waxy solid or viscous oil.
 
Solubility:Soluble in DMSO (25mg/ml) or 100% ethanol (25mg/ml).
 
Shipping:Ambient
 
Long Term Storage:-20°C
 
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.
 
Technical Info/Product Notes:Note: Product is not sterile
 
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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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