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860496O

Avanti

Dimethyl Sphingosine (d18:1)

N,N-dimethyl-D-erythro-sphingosine, neat oil

Synonyme(s) :

(2R,3S,E)-2-(dimethylamino)octadec-4-ene-1,3-diol, N,N-DMS, D-erythro-N,N-dimethylsphingosine

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About This Item

Formule empirique (notation de Hill):
C20H41NO2
Numéro CAS:
Poids moléculaire :
327.55
Code UNSPSC :
12352211
Nomenclature NACRES :
NA.25

Forme

liquid

Conditionnement

pkg of 1 × 5 mg (860496O-5mg)

Fabricant/nom de marque

Avanti Research - A Croda Brand 860496O

Type de lipide

sphingolipids

Conditions d'expédition

dry ice

Température de stockage

−20°C

Chaîne 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

Clé InChI

YRXOQXUDKDCXME-YIVRLKKSSA-N

Description générale

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.

Actions biochimiques/physiologiques

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.

Conditionnement

5 mL Clear Glass Sealed Ampule (860496O-5mg)

Informations légales

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Code de la classe de stockage

10 - Combustible liquids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable


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Consulter la Bibliothèque de documents

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)
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)
Juliana Fraga Vasconcelos et al.
Scientific reports, 7(1), 6171-6171 (2017-07-25)
Chagas disease cardiomyopathy is a parasite-driven inflammatory disease to which there are no effective treatments. Here we evaluated the therapeutic potential of N,N-dimethylsphingosine(DMS), which blocks the production of sphingosine-1-phosphate(S1P), a mediator of cellular events during inflammatory responses, in a model
Hyo-Lim Kim et al.
Prostaglandins & other lipid mediators, 86(1-4), 68-72 (2008-05-10)
Previously, we studied N,N-dimethyl-D-erythro-sphingosine (DMS)-induced cell death and signaling in U937 human monocytes; we found that DMS-induced sphingosine kinase- and PKC-independent apoptosis. In the present study, we studied apoptotic responses by three N-methyl derivatives of sphingosine: N-monomethyl-D-erythro-sphingosine (MMS), N,N,N-trimethyl-D-erythro-sphingosine (TMS)

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