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N,N-Dimethylsphingosine, D-erythro

BML-SL105

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Sphingosine kinase inhibitor

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.

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Product Details

Alternative Name	N,N-Dimethyl-D-erythro-sphingosine
Appearance	White to off-white waxy solid or viscous oil.
CAS	119567-63-4
Couple Target	PKC, Sphingosine kinase
Couple Type	Inhibitor
Formula	C₂₀H₄₁NO₂
MW	327.6
Purity	≥98% (TLC)
Solubility	Soluble in DMSO (25mg/ml) or 100% ethanol (25mg/ml).
Source	Synthetic.
Technical Info / Product Notes	Note: Product is not sterile

Handling & Storage

Use/Stability	As indicated on product label or CoA when stored as recommended. 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.
Long Term Storage	-20°C
Shipping	Ambient Temperature

Regulatory Status	RUO – Research Use Only

Sphingosine and Sphingosine Kinase 1 Involvement in Endocytic Membrane Trafficking: Lima, S., Milstien, S., et al.; J. Biol. Chem. 292, 3074 (2017), Abstract
Metabolomics implicates altered sphingolipids in chronic pain of neuropathic origin: G.J. Patti, et al.; Nat. Chem. Biol. 8, 232 (2012), Abstract
Isoflurane attenuates blood-brain barrier disruption in ipsilateral hemisphere after subarachnoid hemorrhage in mice: Altay, O., Suzuki, H., et al.; Stroke 43, 2513 (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