PSYCHOSINE
Synonym(s):D-galactosyl-β1-1′-D-erythro-sphingosine;Galactosyl(β) sphingosine
- CAS NO.:2238-90-6
- Empirical Formula: C24H47NO7
- Molecular Weight: 461.63
- MDL number: MFCD07374280
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-10-30 18:52:02
What is PSYCHOSINE?
Description
Galactosylsphingosine is a bioactive sphingolipid. It potentiates LPS-induced production of inflammatory cytokines, decreases the mitochondrial membrane potential, and induces cell death in mouse astrocytes, effects that can be reversed by the sphingosine-1-phosphate receptor agonist FTY720 phosphate . Galactosylsphingosine (0.1 and 1 μM) induces demyelination of mouse cerebellar slices. It inhibits PDGF-induced translocation of PKC to the cell surface and induces apoptosis in MO3.13 oligodendrocytes. Galactosylsphingosine (10 and 15 μM) inhibits gene transcription mediated by peroxisome proliferator-activated receptor α (PPARα) in reporter assays using C6 glial cells. Levels of galactosylsphingosine are increased in postmortem brain from patients with Krabbe disease, a lysosomal storage disorder characterized by a β-galactosylceramidase deficiency.[Matreya, LLC. Catalog No. 1305]
The Uses of PSYCHOSINE
Psychosine is a cationic lysosphingolipid that displays neuroprotective effects against quisqualate.
What are the applications of Application
Psychosine is a cationic lysosphingolipid that displays neuroprotective effects against quisqualate
Definition
ChEBI: A glycosylsphingoid consisting of sphingosine having a beta-D-galactosyl residue attached at the 1-position.
General Description
Galactosyl(β) Sphingosine (d18:1) is a substrate for the enzyme endoglycoceramidase I (EGCase I). It has sphingosine backbone with galactose attached to it and is a brain glycospingolipid.
Biochem/physiol Actions
Galatosylsphingosine or psychosine is a cytotoxic lipid which accumulates in oligodendrocytes due to dysfunctional lysosomal enzyme galactosylceramidase and is implicated in globoid cell leukodystrophy. Psychosine accumulation induces demyelination, astrocyte dysfunction and pro-inflammatory cytokine release in Krabbe disease.
Enzyme inhibitor
This cationic brain lysosphingolipid (FWfree-base = 461.64 g/mol; CAS 2238- 90-6), also known as 1-O-b-D-galactosylsphingosine, inhibits metabotropic a1-adrenergic receptor signaling-induced phospholipase C activation in rat brain astrocytes. Psychosine also exerts protective effects against quisqualate, suggesting it may be useful in prophylaxis of neurodegenerative disorders arising from over-stimulation of hippocampal Group 1 metabolotropic glutamate receptor, or mGluR. Psychosine is the product of the reaction catalyzed by sphingosine b-galactosyltransferase and is the substrate for psychosine sulfotransferase and galactosylceramidase. Target(s): cerebroside-sulfatase, or arylsulfatase A; cytochrome c oxidase; cytokinesis; electron transport; galactosylgalactosylglucosylceramidase; glucocerebrosidase, lysosome; b-glucosidase; phosphorylase kinase; protein kinase C (11- 14); protein-tyrosine sulfotransferase; and sphingomyelinase.
Properties of PSYCHOSINE
Melting point: | 190 °C (decomp) |
Boiling point: | 664.3±55.0 °C(Predicted) |
Density | 1.14±0.1 g/cm3(Predicted) |
storage temp. | -20°C |
solubility | Chloroform/Methanol/DI water (5:1:0.1): soluble; Ethanol: soluble |
form | lyophilized powder |
pka | 11.74±0.45(Predicted) |
color | White to off-white |
Safety information for PSYCHOSINE
Signal word | Danger |
Pictogram(s) |
Flame Flammables GHS02 Skull and Crossbones Acute Toxicity GHS06 Health Hazard GHS08 |
GHS Hazard Statements |
H225:Flammable liquids H370:Specific target organ toxicity, single exposure |
Precautionary Statement Codes |
P210:Keep away from heat/sparks/open flames/hot surfaces. — No smoking. P260:Do not breathe dust/fume/gas/mist/vapours/spray. P280:Wear protective gloves/protective clothing/eye protection/face protection. P370+P378:In case of fire: Use … for extinction. P403+P233:Store in a well-ventilated place. Keep container tightly closed. |
Computed Descriptors for PSYCHOSINE
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