2238-90-6

Usage

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

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

Downstream Products

• 35823-61-1 N-Acetylpsychosine 
• 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 
• 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 
• 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 
• 173067-84-0 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 
• 173067-86-2 2,3,6-tri-O-benzoyl-β-D-galactopyranosyl-(1<*>1)-(2S,3R,4E)-3-O-benzoyl-2-dichloroacetamido-4-octadecen-1,3-diol 
• 173067-85-1 2,3-di-O-benzoyl-β-D-galactopyranosyl-(1<*>1)-(2S,3R,4E)-3-O-benzoyl-2-dichloroacetamido-4-octadecen-1,3-diol 
• 173067-83-9 4,6-O-p-methoxybenzylidene-β-D-galactopyranosyl-(1<*>1)-(2S,3R,4E)-2-dichloroacetamido-4-octadecen-1,3-diol 
• 73039-25-5 erythro-N-oleoyl-1-O-β-D-galactosyl-D-sphingosine 
• 41613-16-5 C₃₂H₆₁NO₈ 
• 34324-89-5 (2S,3R,4E)-1-(β-D-galactopyranosyloxy)-2-(hexadecanoylamino)-3-hydroxyoctadec-4-ene 
• 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 

Relevant academic research and scientific papers

3-O-SULFO-GALACTOSYLCERAMIDE ANALOGS AS ACTIVATORS OF TYPE II NKT CELLS AND USES THEREOF

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.

Glycosynthase mediated synthesis of psychosine

Globoid cell leukodystrophy (GCL), or Krabbe disease, is a lysosomal storage disorder characterized by a deficiency in galactosylceramidase (GALC), which hydrolyses galactosylceramide and galactosylsphingosine (psychosine). Early detection of GCL in newborns is essential for timely therapeutic intervention and could be achieved by testing infant blood samples with isotopically labeled lysosmal enzyme substrates and mass spectrometry. While isotopically labeled psychosine would be a useful tool for the early diagnosis of GCL, its synthesis is lengthy and expensive. To obviate this problem we developed a one-step chemoenzymatic synthesis of psychosine using a glycosynthase mutant of the Rhodococcus equi endogalactosylceramidase (EGALC), α-D-galactopyranosyl fluoride and sphingosine.

Synthesis and biological evaluation of antifungal activities of novel 1,2-trans glycosphingolipids

The synthesis and in-vitro biological evaluation of antifungal activities of a series of 1,2-trans glycosphingolipids (GSL) against Candida albicans, Candida parapsilosis, and Candida tropicalis were described. The preliminary study indicated that the sor

Pyridinecarboxamide or trimethoxybenzamide compounds derived from nitrogenous lipids, pharmaceutical compositions containing same which possess anti-convalsive and anti-epileptic properties

Organic amide compounds of the formula STR1 wherein R1 --CO is a residue of a carboxylic acid with the proviso that the carboxylic acid is not a natural fatty acid normally bound to nitrogen of nitrogenous lipids, R2 is a hydrogen atom, a C1-7 alkyl group, or a C4-7 cycloalkyl group, and R3-N is a residue of a nitrogenous lipid. The compounds are useful in increasing or stimulating the in vivo biological activity of in vitro biologically active carboxylic acids.