2. Immunology/Inflammation Apoptosis
  3. SphK Apoptosis
  4. N,N-Dimethylsphingosine

N,N-Dimethylsphingosine is a sphingosine kinase inhibitor. N,N-Dimethylsphingosine binds competitively to sphingosine kinase and blocks the conversion of sphingosine to sphingosine-1-phosphate. N,N-Dimethylsphingosine inhibits sphingosine-1-phosphate release and aggregation of platelets, and also exerts pro-apoptotic effects by resetting ceramide/sphingosine-1-phosphate homeostasis. N,N-Dimethylsphingosine can be used in cancer-related research.

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N,N-Dimethylsphingosine

N,N-Dimethylsphingosine Chemical Structure

CAS No. : 119567-63-4

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Solvent
5 mg (76.32 mM * 200 μL in Ethanol) In-stock
Solvent
10 mg (76.32 mM * 400 μL in Ethanol) In-stock

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Based on 1 publication(s) in Google Scholar

Other Forms of N,N-Dimethylsphingosine:

N,N-Dimethylsphingosine Related Antibodies

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1 Publications Citing Use of MCE N,N-Dimethylsphingosine

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Description

N,N-Dimethylsphingosine is a sphingosine kinase inhibitor. N,N-Dimethylsphingosine binds competitively to sphingosine kinase and blocks the conversion of sphingosine to sphingosine-1-phosphate. N,N-Dimethylsphingosine inhibits sphingosine-1-phosphate release and aggregation of platelets, and also exerts pro-apoptotic effects by resetting ceramide/sphingosine-1-phosphate homeostasis. N,N-Dimethylsphingosine can be used in cancer-related research[1][2][3].

Cellular Effect
Cell Line Type Value Description References
CHO IC50
5.7 μM
Compound: DMS
Inhibition of EGFP-fused human SPHK1 expressed in CHO cells
Inhibition of EGFP-fused human SPHK1 expressed in CHO cells
[PMID: 19469544]
FL5.12 IC50
0.8 μM
Compound: 8
Cytotoxicity against mouse FL5.12A cells after 48 hrs by DAPI staining-based flow cytometric analysis
Cytotoxicity against mouse FL5.12A cells after 48 hrs by DAPI staining-based flow cytometric analysis
[PMID: 27475534]
RAW264.7 IC50
2.3 μM
Compound: N,N-Dimethylsphingosine
Protection against Bacillus anthracis lethal toxin-mediated cytotoxicity in mouse RAW264.7 cells assessed as change in viability after 24 hrs by WST1 dye reduction assay
Protection against Bacillus anthracis lethal toxin-mediated cytotoxicity in mouse RAW264.7 cells assessed as change in viability after 24 hrs by WST1 dye reduction assay
[PMID: 17485504]
In Vitro

N,N-Dimethylsphingosine (0.2-50 µM; 5 min) inhibits sphingosine kinase activity in human platelets, with an IC50 of approximately 10 µM[1].
N,N-Dimethylsphingosine (0.2-50 µM; 1 h) inhibits sphingosine kinase activity in cell-free cytosolic fractions of human platelets, with an IC50 of approximately 5 µM[1].
N,N-Dimethylsphingosine (25 µM; 1 min pretreatment) inhibits TPA (HY-18739)-induced sphingosine-1-phosphate release in human platelets[1].
N,N-Dimethylsphingosine (5-50 µM; 30 min) is a potent competitive inhibitor of sphingosine kinase, with Ki values of 3.1 µM, 2.3 µM, and 6.8 µM in cytoplasmic extracts of U937, Swiss 3T3, and PC12 cells, respectively[2].
N,N-Dimethylsphingosine (10-20 μM; 4-6 h) induces apoptosis in human leukemia cell lines CMK-7, HL60 and U937[3].
N,N-Dimethylsphingosine (5-20 μM; 6-12 h) induces apoptosis in human cancer cell lines A431, MKN74, HT29, HRT18 and COLO205[3].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

N,N-Dimethylsphingosine Related Antibodies

Apoptosis Analysis[3]

Cell Line: CMK-7, HL60, U937 human leukemic cell lines
Concentration: 10 μM, 20 μM
Incubation Time: 4 h, 6 h
Result: Induced apoptosis in 65% of CMK-7 cells, 85% of HL60 cells, and 50% of U937 cells after treatment with 20 μM for 6 h.
Revealed condensed/fragmented nuclei, apoptotic bodies, and membrane blebbing in cells treated with 20 μM for 4 h.
Demonstrated clear internucleosomal ladder formation in all three cell lines treated with 10 μM or 20 μM for 4 h or 6 h, with nearly complete DNA fragmentation observed by 6 h.
Molecular Weight

327.55

Formula

C20H41NO2
CAS No.
Appearance

Liquid

Color

Colorless to light yellow

SMILES

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

Room temperature in continental US; may vary elsewhere.
Storage

Solution, -20°C, 2 years
Purity & Documentation

Purity: 99.93%

SDS (570 KB)

COA (239 KB) HNMR (251 KB) LCMS (90 KB)

Handling Instructions (2659 KB)
References
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N,N-Dimethylsphingosine Related Classifications

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Help & FAQs
  • Do most proteins show cross-species activity?

    Species cross-reactivity must be investigated individually for each product. Many human cytokines will produce a nice response in mouse cell lines, and many mouse proteins will show activity on human cells. Other proteins may have a lower specific activity when used in the opposite species.

Keywords:

N,N-Dimethylsphingosine119567-63-4SphKApoptosisSphingosine kinasesphingosineU937 cellshuman plateletssphingosine kinasePC12 cellsA431 cellsSwiss 3T3 cellsceramidesphingosine 1-phosphateHL60 cellsInhibitorinhibitorinhibit

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