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SML0311

Sigma-Aldrich

N,N-Dimethylsphingosine

≥98% (HPLC)

Sinônimo(s):

N,N-Dimethylsphingosine, (2S,3R,4E)-2-(Dimethylamino)-4-octadecene-1,3-diol, D-Erythro-N,N-Dimethylsphingosine, DMS, Dimethylsphingosine

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About This Item

Fórmula empírica (Notação de Hill):
C20H41NO2
Número CAS:
119567-63-4
Peso molecular:
327.55
Número MDL:
MFCD02259309
Código UNSPSC:
12352211
ID de substância PubChem:
329825316
NACRES:
NA.77

Ensaio

≥98% (HPLC)

forma

film

cor

colorless

temperatura de armazenamento

−20°C

cadeia de caracteres SMILES

OC[C@@](N(C)C)([H])[C@]([H])(O)/C=C/CCCCCCCCCCCCC

InChI

1S/C20H41NO2/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)19(18-22)21(2)3/h16-17,19-20,22-23H,4-15,18H2,1-3H3/b17-16+/t19-,20+/m0/s1

chave InChI

YRXOQXUDKDCXME-YIVRLKKSSA-N

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Aplicação

N,N-Dimethylsphingosine has been used as an internal standard in liquid chromatography with tandem mass spectrometry (LC-MS-MS) for psychosine quantification in fibroblasts from twitcher (TWI) and wild type mice. It has also been used as an inhibitor of sphingosine kinase (SphK) to investigate the role of SphK in enhancing lipopolysaccharide (LPS)-mediated chemokine expression.

Ações bioquímicas/fisiológicas

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.

Características e benefícios

This compound is a featured product for Kinase Phosphatase Biology research. Click here to discover more featured Kinase Phosphatase Biology products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Certificados de análise (COA)

Busque Certificados de análise (COA) digitando o Número do Lote do produto. Os números de lote e remessa podem ser encontrados no rótulo de um produto após a palavra “Lot” ou “Batch”.

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A Muscella et al.
British journal of pharmacology, 153(1), 34-49 (2007-11-21)
We showed previously that a new Pt complex containing an O,O'-chelated acetylacetonate ligand (acac) and a dimethylsulphide in the Pt coordination sphere, [Pt(O,O'-acac)(gamma-acac)(DMS)], induces apoptosis in HeLa cells. The objective of this study was to investigate the hypothesis that [Pt(O,O'-acac)(gamma-acac)(DMS)]
Christopher C Wendler et al.
Developmental biology, 291(2), 264-277 (2006-01-26)
Sphingosine-1-phosphate (S1P) is a biologically active sphingolipid metabolite that exerts important effects on numerous cellular events via cell surface receptors, S1P(1-5). S1P influences differentiation, proliferation, and migration during vascular development. However, the effects of S1P signaling on early cardiac development
Sinead A O'Sullivan et al.
Journal of neurochemistry, 144(6), 736-747 (2018-01-30)
Sphingosine 1-phosphate receptors (S1PR) are G protein-coupled and compose a family with five subtypes, S1P1R-S1P5R. The drug Gilenya® (Novartis, Basel, Switzerland) (Fingolimod; FTY720) targets S1PRs and was the first oral therapy for patients with relapsing-remitting multiple sclerosis (MS). The phosphorylated
S Kimura et al.
Biochemical pharmacology, 44(8), 1585-1595 (1992-10-20)
Neutrophils display three major functions: (i) oxidative burst, (ii) phagokinetic activity, and (iii) trans-endothelial migration. Sphingosine (SPN) is known to inhibit oxidative burst in human neutrophils via inhibition of protein kinase C (PKC). SPN is metabolically converted into N,N-dimethylsphingosine (DMS)
K Endo et al.
Cancer research, 51(6), 1613-1618 (1991-03-15)
Sphingosine (SPN) has been claimed to be a negative modulator of transmembrane signaling through protein kinase C (PK-C) or some yet unidentified mechanism [for review see Y. A. Hannun and R. M. Bell, Science (Washington DC), 243: 500-507, 1989]. N,N-Dimethylsphingosine
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