PSYCHOSINE
PSYCHOSINE Basic information
- Product Name:
- PSYCHOSINE
- Synonyms:
-
- SPHINGOSYL-BETA-D-GALACTOPYRANOSIDE
- SPHINGOSINE, 1-BETA-D-GALACTOSYL
- PSYCHOSIN
- b-D-Galactosylsphingosine - Synthetic
- PSYCHOSINE
- 1-BETA-D-GALACTOSYLSPHINGOSINE
- 1-B-D-GALACTOSYLSPHINOGOSINE
- LYSO-CERAMIDEGALACTOSIDE
- CAS:
- 2238-90-6
- MF:
- C24H47NO7
- MW:
- 461.63
- Product Categories:
-
- Miscellaneous Natural Products
- Mol File:
- 2238-90-6.mol
PSYCHOSINE Chemical Properties
- 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
PSYCHOSINE Usage And Synthesis
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]
Uses
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.
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PSYCHOSINE(2238-90-6)Related Product Information
- PSYCHOSINE
- PSYCHOSINE
- N-ACETYL-PSYCHOSINE, C2-CEREBROSIDE,N-ACETYL-PSYCHOSINE
- D-ERYTHRO-SPHINGOSINE
- N-STEAROYL-D35-PSYCHOSINE
- N-Pentadecanoyl-psychosine?
- N-STEAROYL-PSYCHOSINE
- BODIPY(R) FL C12-GALACTOCEREBROSIDE
- GALACTOSYL CERAMIDE, [GALACTOSE-6-3H]
- PSYCHOSINE, [GALACTOSE-6-3H]
- psychosine-3'-sulfate ester
- Psychosine from bovine brain
- 2,3,4,6-TETRA-O-ACETYL-BETA-D-GALACTOPYRANOSY(1-4)-2,3,6-TRI-O-ACETYL-BETA-D-GLUCOPYRANOSYL CERAMIDE
- TNPAL-GALACTOCEREBROSIDE
- C6 NBD GALACTOSYL CERAMIDE
- C24:0-SULFATIDE
- N-STEAROYL-D35-PSYCHOSINE, PERDEUTERATED
- PSYCHOSINE, N-ACETYL