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N,N-Dimethyl-Sphingosine

N,N-Dimethyl sphingosine inhibits sphingosine kinase 1 (Sphk1) and PKC and exhibits neuromodulatory and anticancer chemotherapeutic activities. This compound activates protein phosphatase 2A (PP2A) activity by suppressing ANP32A inhibition of PP2A in vitro. Additionally, this compound inhibits cell proliferation and tumor growth in cellular and animal models of gastric carcinoma.

References PubMed ID::http://www.ncbi.nlm.nih.gov/pubmed/18947320

Cas No.

119567-63-4

Purity

≥98%

Formula

C20H41NO2

Formula Wt.

327.5

Chemical Name

4-Octadecene-1,3-diol, 2-(dimethylamino)-, (R-(R*,S*-(E)))-

IUPAC Name

(E,2S,3R)-2-(dimethylamino)octadec-4-ene-1,3-diol

Synonym

N,N-Dimethyl-D-erythro-sphingosine

Solubility

Soluble in DMSO or ethanol.

Appearance

White to off white waxy solid or viscous oil

Rosa R, Marciano R, Malapelle U, et al. Sphingosine kinase 1 overexpression contributes to cetuximab resistance in human colorectal cancer models. Clin Cancer Res. 2013 Jan 1;19(1):138-47. PMID: 23166225.

Habrukowich C, Han DK, Le A, et al. Sphingosine interaction with acidic leucine-rich nuclear phosphoprotein-32A (ANP32A) regulates PP2A activity and cyclooxygenase (COX)-2 expression in human endothelial cells. J Biol Chem. 2010 Aug 27;285(35):26825-31. PMID: 20558741.

Endo K, Igarashi Y, Nisar M, et al. Cell membrane signaling as target in cancer therapy: inhibitory effect of N,N-dimethyl and N,N,N-trimethyl sphingosine derivatives on in vitro and in vivo growth of human tumor cells in nude mice. Cancer Res. 1991 Mar 15;51(6):1613-8. PMID: 1998952.

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