Description
N,N-Dimethylsphingosine (119567-63-4) is a synthetic derivative of D-erythro-sphingosine (Cat.# 10-2287). Endogenous sphingolipid.1Inhibits sphingosine kinase (IC50 = 5 μM).2N,N-Dimethylsphingosine induces apoptosis in a variety of cell lines.3
Chemical Properties
Colourless to Light Yellow Oil
Uses
A general modulator of protein kinases.
Uses
N,N-Dimethylsphingosine is an inhibitor of sphingosine kinase (SPHK). It is a natural metabolite of sphingosine in some cancer cell lines and tissues. N,N-Dimethylsphingosine inhibited U937 cell SPHK with a Ki value of 3.1 μM. N,N-Dimethylsphingosine induces apoptosis, but it is not an inhibitor of protein kinase C.
Uses
D-erythro-N,N-Dimethylsphingosine is general modulator of protein kinases . D-erythro-N,N-Dimethylsphingosine is implicated in neuropathic pain.
Definition
ChEBI: N,N-dimethylsphingosine is a sphingoid that is sphingosine in which the two amino hydrogens are replaced by methyl groups. It has a role as a metabolite and an EC 2.7.1.91 (sphingosine kinase) inhibitor. It is an aminodiol, a sphingoid and a tertiary amino compound. It is functionally related to a sphingosine. It is a conjugate base of a N,N-dimethylsphingosine(1+).
General Description
Dimethyl Sphingosine (d18:1), also called as
N,N-Dimethyl-d-
erythro-sphingosine (DMS), is a natural sphingolipid metabolite. It is found in various tissues.
Biochem/physiol Actions
N,N-Dimethylsphingosine (DMS) is an endogenous metabolite of sphingosine produced in various tissues and tumor cell lines. N,N-Dimethylsphingosine is a potent inhbitor of sphingosine kinase. DMS levels are elevated in the spinal cord, and contributes to allodynia, in a transected-nerve model of neuropathic pain.
References
[1] Y IGARASHI. 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.[J]. The Journal of Biological Chemistry, 1990, 265 10: 5385-5389.
[2] YUTAKA YATOMI. N,N-Dimethylsphingosine Inhibition of Sphingosine Kinase and Sphingosine 1-Phosphate Activity in Human Platelets†[J]. Biochemistry Biochemistry, 1996, 35 2: 626-633. DOI:
10.1021/bi9515533[3] DAVID R. GUDE. Apoptosis induces expression of sphingosine kinase 1 to release sphingosine-1-phosphate as a “come-and-get-me” signal[J]. FASEB Journal, 2008, 22 8: 2629-2638. DOI:
10.1096/fj.08-107169
