D-Sphingosine

Sphingosine is formed primarily from the breakdown of ceramide. Sphingosine inhibits protein kinase C and phosphatidic acid phosphohydrolase. D-sphingosine, a lipid possessing the same hydrophobic base as ceramide but without a carbohydrate residue, efficiently blocked this glycolipid antigen presentation both in vitro and in spinal cords of EAE mice, and significantly decreased IL-17 and ameliorated the pathological symptoms.

Product information

CAS Number: 123-78-4

Molecular Weight: 299.49

Formula: C18H37NO2

Synonym:

(−)-Sphingosine

Sphingosine (d18:1)

erythro-Sphingosine C-18

Chemical Name: 2S-amino-4E-octadecene-1,3R-diol

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

InChiKey: WWUZIQQURGPMPG-KRWOKUGFSA-N

InChi: InChI=1S/C18H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h14-15,17-18,20-21H,2-13,16,19H2,1H3/b15-14+/t17-,18+/m0/s1

Technical Data

Appearance: Solid Power.

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: Soluble in DMSO

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥12 months if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined.

HS Tariff Code: 382200

How to use

In Vitro:

A p32-sphingosine-activated protein kinase responds to low concentrations of D-erythro-Sphingosine with an initial activation observed at 2.5 μM and a peak activity at 10-20 μM. This kinase shows a modest specificity for D-erythro-Sphingosine over other sphingosine tereoisomers, and a preference for sphingosines over ihydrosphingosines. D-erythro-Sphingosine inhibits protein kinase C in vitro. D-erythro-Sphingosine has been shown to inhibit protein kinase C, which affects cell regulation and several signal transduction pathways, and exhibits antitumor promoter activities in various mammalian cells.

References:

1. Resuello DL, Lirio SB, Porto AE, Macabeo APG, Huang HY, Corpuz MJT, Villaflores OB. β-secretase 1 inhibitory activity and AMP-activated protein kinase activation of Callyspongia samarensis extracts. Nat Prod Res. 2020 Feb;34(4):525-529. doi: 10.1080/14786419.2018.1488699. Epub 2018 Nov 14. PMID: 30427208.
2. Cleary JM, Lipsky ZW, Kim M, Marques CNH, German GK. Heterogeneous ceramide distributions alter spatially resolved growth of Staphylococcus aureus on human stratum corneum. J R Soc Interface. 2018 Apr;15(141):20170848. doi: 10.1098/rsif.2017.0848. PMID: 29669890; PMCID: PMC5938579.
3. Pavlova NV, Li SC, Li YT. Degradation of glycosphingolipids in oyster: ceramide glycanase and ceramidase in the hepatopancreas of oyster, Crassostrea virginica. Glycoconj J. 2018 Feb;35(1):77-86. doi: 10.1007/s10719-017-9802-7. Epub 2017 Oct 16. PMID: 29039121.

Products are for research use only. Not for human use.