2238-90-6

Basic information

• Product Name: PSYCHOSINE
• Synonyms: SPHINGOSYL-BETA-D-GALACTOPYRANOSIDE;SPHINGOSINE, 1-BETA-D-GALACTOSYL;PSYCHOSIN;PSYCHOSINE;LYSO-CERAMIDEGALACTOSIDE;LYSO-CEREBROSIDE;D-GALACTOSYL-B1-1'-D-ERYTHRO-SPHINGOSINE;D-GALACTOSYL-B1-1' SPHINGOSINE
• CAS NO: 2238-90-6
• Molecular Formula: C₂₄H₄₇NO₇
• Molecular Weight: 461.63
• Product Categories: Miscellaneous Natural Products
• Mol File: 2238-90-6.mol
• Article Data: 4

Chemical Properties

• Melting Point: 190 °C (decomp)
• Boiling Point: 664.3ºC
• Flash Point: 355.6 ºC
• Appearance: White powder
• Density: 1.14 g/cm³
• Vapor Pressure: 1.77E-20mmHg at 25°C
• Refractive Index: 1.535
• Storage Temp.: −20°C
• PKA: 11.74±0.45(Predicted)
• CAS DataBase Reference: PSYCHOSINE(CAS DataBase Reference)
• NIST Chemistry Reference: PSYCHOSINE(2238-90-6)
• EPA Substance Registry System: PSYCHOSINE(2238-90-6)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36
• WGK Germany: 3
• Hazardous Substances Data: 2238-90-6(Hazardous Substances Data)

Usage

Description

Psychosine, also known as Galactosylsphingosine, is a cationic lysosphingolipid and a bioactive sphingolipid with a sphingosine backbone and galactose attached to it. It is a brain glycosphingolipid and a substrate for the enzyme endoglycoceramidase I (EGCase I). Psychosine displays neuroprotective effects against quisqualate and has been found to have various biological activities, including potentiating LPS-induced production of inflammatory cytokines, decreasing mitochondrial membrane potential, and inducing cell death in mouse astrocytes.

Uses

Used in Neuroprotection:
Psychosine is used as a neuroprotective agent for its ability to protect against excitotoxic neuronal injury caused by quisqualate. Its neuroprotective effects make it a potential candidate for the treatment of neurodegenerative diseases.
Used in Research on Krabbe Disease:
Psychosine is used in research for studying Krabbe disease, a lysosomal storage disorder characterized by a β-galactosylceramidase deficiency. Increased levels of psychosine have been found in postmortem brain samples from patients with Krabbe disease, making it a potential biomarker for the condition.
Used in Cellular and Molecular Research:
Psychosine is used as a research tool to investigate its effects on various cellular processes, such as demyelination of mouse cerebellar slices, inhibition of PDGF-induced translocation of PKC to the cell surface, and induction of apoptosis in MO3.13 oligodendrocytes. Additionally, it is used to study its inhibitory effects on gene transcription mediated by peroxisome proliferator-activated receptor α (PPARα) in reporter assays using C6 glial cells.
Used in Drug Development:
Psychosine's biological activities and potential therapeutic effects make it a candidate for drug development, particularly in the areas of neuroprotection and treatment of lysosomal storage disorders. Its ability to modulate various cellular processes and signaling pathways could lead to the development of novel therapeutic agents targeting neurodegenerative diseases and other conditions.

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.

InChI:InChI=1/C24H47NO7/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19(27)18(25)17-31-24-23(30)22(29)21(28)20(16-26)32-24/h14-15,18-24,26-30H,2-13,16-17,25H2,1H3/b15-14+/t18?,19?,20-,21+,22+,23-,24-/m1/s1

Upstream product

• 2021-84-3 α-galactosyl fluoride 
• 123-78-4 (2S,3R,4E)-2-amino-4-octadecene-1,3-diol 
• 118605-55-3 (2,3,4,6-tetra-O-pivaloyl-α-D-galactopyranoside)-1-trichloroacetimidate 
• 118711-45-8 (2S,3R,4E)-2-azido-1-(galactopyranosyloxy)octadec-4-en-3-ol 
• 916159-70-1 (2S,3R)-(E)-2-azido-1-(tert-butyldiphenylsilyloxy)octadec-4-en-3-ol 
• 103348-50-1 (2S,3R,4E)-2-azido-3-benzoyloxy-4-octadecen-1-ol 

Downstream Products

• 36271-49-5 (2S,3R,4E)-1-(β-D-galactopyranosyloxy)-2-(octadecanoylamino)-3-hydroxyoctadec-4-ene 
• 17283-91-9 (2S,3R,4E)-1-(β-D-galactopyranosyloxy)-2-(15(Z)-tetracosenoylamino)-3-hydroxyoctadec-4-ene 
• 34324-89-5 (2S,3R,4E)-1-(β-D-galactopyranosyloxy)-2-(hexadecanoylamino)-3-hydroxyoctadec-4-ene 
• 35823-61-1 N-Acetylpsychosine 
• 41613-16-5 C₃₂H₆₁NO₈ 
• 73039-25-5 erythro-N-oleoyl-1-O-β-D-galactosyl-D-sphingosine 
• 173067-83-9 4,6-O-p-methoxybenzylidene-β-D-galactopyranosyl-(1<*>1)-(2S,3R,4E)-2-dichloroacetamido-4-octadecen-1,3-diol 
• 173067-85-1 2,3-di-O-benzoyl-β-D-galactopyranosyl-(1<*>1)-(2S,3R,4E)-3-O-benzoyl-2-dichloroacetamido-4-octadecen-1,3-diol 
• 173067-86-2 2,3,6-tri-O-benzoyl-β-D-galactopyranosyl-(1<*>1)-(2S,3R,4E)-3-O-benzoyl-2-dichloroacetamido-4-octadecen-1,3-diol 
• 173067-84-0 2,3-di-O-benzoyl-4,6-O-p-methoxybenzylidene-β-D-galactopyranosyl-(1<*>1)-(2S,3R,4E)-3-O-benzoyl-2-dichloroacetamido-4-octadecen-1,3-diol 
• 173067-87-3 2,3,6-tri-O-benzoyl-4-O-trifluoromethylsulfonyl-β-D-galactopyranosyl-(1<*>1)-(2S,3R,4E)-3-O-benzoyl-2-dichloroacetamido-4-octadecen-1,3-diol 
• 173067-88-4 S-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1<*>4)-2,3,6-tri-O-benzoyl-4-thio-β-D-glucopyranosyl-(1<*>1)-(2S,3R,4E)-3-O-benzoyl-2-dichloroacetamido-4-octadecen-1,3-diol 
• 88035-98-7 2-Hydroxy-N-[(E)-2-hydroxy-1-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl)-heptadec-3-enyl]-malonamic acid tetradecyl ester 

Relevant articles and documents

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Disclosed is a compound of the formula (I) or (II): wherein a f are as described herein. The compounds are useful in the activation of Type II NKT cells and in treating cancer.

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