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经验公式（希尔记法）:
C20H41NO2
化学文摘社编号:
分子量:
327.55
MDL number:
UNSPSC Code:
12352211
NACRES:
NA.25
产品名称
Dimethyl Sphingosine (d18:1), N,N-dimethyl-D-erythro-sphingosine, neat oil
SMILES string
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
InChI key
YRXOQXUDKDCXME-YIVRLKKSSA-N
assay
>99% (TLC)
form
liquid
packaging
pkg of 1 × 5 mg (860496O-5mg)
manufacturer/tradename
Avanti Research™ - A Croda Brand 860496O
lipid type
sphingolipids
shipped in
dry ice
storage temp.
−20°C
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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.
Application
Dimethyl Sphingosine (d18:1) may be used:
- to investigate D-erythro-N,N-dimethylsphingosine (DMS)-induced cell death in U937 cells to understand its molecular mechanism
- to study its effects on intracellular Ca2+ concentration, pH and glutamate uptake in human 1321N1 astrocytes
- in substrate specificity studies of sphingosine methyltransferase activity in rat kidney homogenate
Dimethyl sphingosine (d18:1) has been used as an inhibitor of sphingosine kinase.
Biochem/physiol Actions
D-erythro-N,N-dimethylsphingosine (DMS) prevents the activity of sphingosine kinase and protein kinase C. It modulates cellular activities. DMS exhibits anti-cancer and apoptotic properties. It is involved in the augmentation of epidermal growth factor receptor (EGFR) and inhibition of src kinase. DMS functions as a potential therapeutic for Chagas disease cardiomyopathy through its anti-parasitic and immunomodulatory properties.
D-erythro-N,N-dimethylsphingosine (DMS) has an ability to inhibit the activity of sphingosine kinase. It also helps to study the role of sphingosine 1-phosphate (SPP) as an intracellular second messenger. DMS exhibits anti-parasitic and immunomodulatory activities. It acts as a potential therapeutic for chronic Chagas disease cardiomyopathy.
Packaging
5 mL Clear Glass Sealed Ampule (860496O-5mg)
Legal Information
Avanti Research is a trademark of Avanti Polar Lipids, LLC
存储类别
10 - Combustible liquids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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
Edsall L, et al.
Biochemistry, 37(37), 12892-12898 (1998)
Hongtao Wang et al.
Molecular cancer therapeutics, 7(9), 2967-2976 (2008-09-16)
Fenretinide [N-(4-hydroxyphenyl)retinamide (4-HPR)] is cytotoxic in many cancer cell types. Studies have shown that elevation of ceramide species plays a role in 4-HPR cytotoxicity. To determine 4-HPR activity in a multidrug-resistant cancer cell line as well as to study ceramide
High-throughput screening assay for sphingosine kinase inhibitors in whole blood using RapidFire mass spectrometry
Highkin MK, et al.
Journal of Biomolecular Screening, 16(2), 272-277 (2011)
N-(4-Hydroxyphenyl) retinamide increases dihydroceramide and synergizes with dimethylsphingosine to enhance cancer cell killing
Wang H, et al.
Molecular Cancer Therapeutics, 7(9), 2967-2976 (2008)
Therapeutic effects of sphingosine kinase inhibitor N, N-dimethylsphingosine (DMS) in experimental chronic Chagas disease cardiomyopathy
Vasconcelos JF, et al.
Scientific reports, 7(1), 6171-6171 (2017)
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