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2238-90-6,MFCD00057505
Catalog No.:AA00BC1O

2238-90-6 | PSYCHOSINE

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  • Technical Information
  • Properties
  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA00BC1O
Chemical Name:
PSYCHOSINE
CAS Number:
2238-90-6
Molecular Formula:
C24H47NO7
Molecular Weight:
461.6325
MDL Number:
MFCD00057505
SMILES:
CCCCCCCCCCCCC/C=C/[C@H]([C@H](CO[C@@H]1O[C@H](CO)[C@@H]([C@@H]([C@H]1O)O)O)N)O
Properties
Properties
 
Form:
Solid  
MP:
190℃ (dec.)  
Storage:
-20 ℃;  

Computed Properties
 
Complexity:
479  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
7  
Defined Bond Stereocenter Count:
1  
Heavy Atom Count:
32  
Hydrogen Bond Acceptor Count:
8  
Hydrogen Bond Donor Count:
6  
Rotatable Bond Count:
18  
XLogP3:
3.7  

Literature

Title: Bone marrow transplantation increases efficacy of central nervous system-directed enzyme replacement therapy in the murine model of globoid cell leukodystrophy.

Journal: Molecular genetics and metabolism 20120901

Title: Detection of the neurotoxin psychosine in samples of peripheral blood: application in diagnostics and follow-up of Krabbe disease.

Journal: Archives of pathology & laboratory medicine 20120701

Title: Psychosine induces the dephosphorylation of neurofilaments by deregulation of PP1 and PP2A phosphatases.

Journal: Neurobiology of disease 20120501

Title: Genome-wide association study of N370S homozygous Gaucher disease reveals the candidacy of CLN8 gene as a genetic modifier contributing to extreme phenotypic variation.

Journal: American journal of hematology 20120401

Title: Ex vivo and in vivo effects of isofagomine on acid β-glucosidase variants and substrate levels in Gaucher disease.

Journal: The Journal of biological chemistry 20120203

Title: Systemic delivery of a glucosylceramide synthase inhibitor reduces CNS substrates and increases lifespan in a mouse model of type 2 Gaucher disease.

Journal: PloS one 20120101

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

Journal: Archiv der Pharmazie 20111201

Title: Effect of functionalization of carbon nanotubes with psychosine on complement activation and protein adsorption.

Journal: Journal of biomedical nanotechnology 20111201

Title: Effect of psychosine on inducible nitric-oxide synthase expression under different culture conditions: implications for Krabbe disease.

Journal: European review for medical and pharmacological sciences 20111101

Title: Elevated plasma glucosylsphingosine in Gaucher disease: relation to phenotype, storage cell markers, and therapeutic response.

Journal: Blood 20111020

Title: Selective extraction and effective separation of galactosylsphingosine (psychosine) and glucosylsphingosine from other glycosphingolipids in pathological tissue samples.

Journal: Neurochemical research 20110901

Title: Bone marrow transplantation augments the effect of brain- and spinal cord-directed adeno-associated virus 2/5 gene therapy by altering inflammation in the murine model of globoid-cell leukodystrophy.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20110706

Title: Axonopathy is a compounding factor in the pathogenesis of Krabbe disease.

Journal: Acta neuropathologica 20110701

Title: Accumulation and distribution of α-synuclein and ubiquitin in the CNS of Gaucher disease mouse models.

Journal: Molecular genetics and metabolism 20110401

Title: Persistence of psychosine in brain lipid rafts is a limiting factor in the therapeutic recovery of a mouse model for Krabbe disease.

Journal: Journal of neuroscience research 20110301

Title: Sphingosylphosphorylcholine and lysosulfatide have inverse regulatory functions in monocytic cell differentiation into macrophages.

Journal: Archives of biochemistry and biophysics 20110201

Title: Accumulation of lysosulfatide in the brain of arylsulfatase A-deficient mice.

Journal: Lipids in health and disease 20110101

Title: Peripheral neuropathy in the Twitcher mouse involves the activation of axonal caspase 3.

Journal: ASN neuro 20110101

Title: How well does urinary lyso-Gb3 function as a biomarker in Fabry disease?

Journal: Clinica chimica acta; international journal of clinical chemistry 20101214

Title: Triglyceride-mediated pathways and coronary heart disease.

Journal: Lancet (London, England) 20100918

Title: A galactose-free diet enriched in soy isoflavones and antioxidants results in delayed onset of symptoms of Krabbe disease in twitcher mice.

Journal: Molecular genetics and metabolism 20100701

Title: Synthesis and properties of a photoactivatable analogue of psychosine (beta-Galactosylsphingosine).

Journal: ChemMedChem 20100503

Title: Neuronopathic Gaucher disease in the mouse: viable combined selective saposin C deficiency and mutant glucocerebrosidase (V394L) mice with glucosylsphingosine and glucosylceramide accumulation and progressive neurological deficits.

Journal: Human molecular genetics 20100315

Title: Factors that affect postnatal bone growth retardation in the twitcher murine model of Krabbe disease.

Journal: Biochimica et biophysica acta 20100101

Title: A possible mechanism underlying the ceramide deficiency in atopic dermatitis: expression of a deacylase enzyme that cleaves the N-acyl linkage of sphingomyelin and glucosylceramide.

Journal: Journal of dermatological science 20090701

Title: Psychosine accumulates in membrane microdomains in the brain of krabbe patients, disrupting the raft architecture.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20090513

Title: Lysosulfatide regulates the motility of a neural precursor cell line via calcium-mediated process collapse.

Journal: Neurochemical research 20090301

Title: Direct quantitation of psychosine from alkaline-treated lipid extracts with a semi-synthetic internal standard.

Journal: Journal of lipid research 20090101

Title: Psychosine-induced alterations in peroxisomes of twitcher mouse liver.

Journal: Archives of biochemistry and biophysics 20080915

Title: The role of AMPK in psychosine mediated effects on oligodendrocytes and astrocytes: implication for Krabbe disease.

Journal: Journal of neurochemistry 20080601

Title: Wheat germ agglutinin stains dispersed post-golgi vesicles after treatment with the cytokinesis inhibitor psychosine.

Journal: Journal of cellular physiology 20080501

Title: Autonomic denervation of lymphoid organs leads to epigenetic immune atrophy in a mouse model of Krabbe disease.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20071212

Title: Psychosine-induced apoptosis and cytokine activation in immune peripheral cells of Krabbe patients.

Journal: Journal of cellular physiology 20070901

Title: Increased TNF-alpha production by peripheral blood mononuclear cells in patients with Krabbe's disease: effect of psychosine.

Journal: European journal of clinical investigation 20070901

Title: The role of lysosphingolipids in the regulation of biological processes.

Journal: Biochemistry. Biokhimiia 20070501

Title: Establishment of a quantitative, qualitative, and high-throughput analysis of sulfatides from small amounts of sera by matrix-assisted laser desorption ionization-time of flight mass spectrometry.

Journal: Analytical biochemistry 20070301

Title: Krabbe disease: psychosine-mediated activation of phospholipase A2 in oligodendrocyte cell death.

Journal: Journal of lipid research 20060701

Title: Intrinsic resistance of neural stem cells to toxic metabolites may make them well suited for cell non-autonomous disorders: evidence from a mouse model of Krabbe leukodystrophy.

Journal: Journal of neurochemistry 20060601

Title: Dysfunction of peroxisomes in twitcher mice brain: a possible mechanism of psychosine-induced disease.

Journal: Biochemical and biophysical research communications 20060428

Title: Proton-sensing and lysolipid-sensitive G-protein-coupled receptors: a novel type of multi-functional receptors.

Journal: Cellular signalling 20051201

Title: Two ligands for a GPCR, proton vs lysolipid.

Journal: Acta pharmacologica Sinica 20051201

Title: Insulin-like growth factor-1 provides protection against psychosine-induced apoptosis in cultured mouse oligodendrocyte progenitor cells using primarily the PI3K/Akt pathway.

Journal: Molecular and cellular neurosciences 20051101

Title: Sphingosylphosphorylcholine antagonizes proton-sensing ovarian cancer G-protein-coupled receptor 1 (OGR1)-mediated inositol phosphate production and cAMP accumulation.

Journal: Journal of pharmacological sciences 20051001

Title: Enzyme replacement therapy results in substantial improvements in early clinical phenotype in a mouse model of globoid cell leukodystrophy.

Journal: FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20050901

Title: Reversal of non-hydroxy:alpha-hydroxy galactosylceramide ratio and unstable myelin in transgenic mice overexpressing UDP-galactose:ceramide galactosyltransferase.

Journal: Journal of neurochemistry 20050701

Title: Hematopoietic cell transplantation ameliorates clinical phenotype and progression of the CNS pathology in the mouse model of late onset Krabbe disease.

Journal: Journal of neuropathology and experimental neurology 20050701

Title: Peroxisomal participation in psychosine-mediated toxicity: implications for Krabbe's disease.

Journal: Journal of neuroscience research 20050615

Title: Early use of drastic therapy.

Journal: The New England journal of medicine 20050519

Title: AAV-mediated expression of galactocerebrosidase in brain results in attenuated symptoms and extended life span in murine models of globoid cell leukodystrophy.

Journal: Molecular therapy : the journal of the American Society of Gene Therapy 20050501

Title: The glucocorticoid-induced gene tdag8 encodes a pro-apoptotic G protein-coupled receptor whose activation promotes glucocorticoid-induced apoptosis.

Journal: The Journal of biological chemistry 20041217

Title: Glycolipid transfer protein mediated transfer of glycosphingolipids between membranes: a model for action based on kinetic and thermodynamic analyses.

Journal: Biochemistry 20041102

Title: TDAG8 is a proton-sensing and psychosine-sensitive G-protein-coupled receptor.

Journal: The Journal of biological chemistry 20041029

Title: Quantitative and qualitative differences in the in vivo response of NKT cells to distinct alpha- and beta-anomeric glycolipids.

Journal: Journal of immunology (Baltimore, Md. : 1950) 20040915

Title: Psychosine-induced apoptosis in a mouse oligodendrocyte progenitor cell line is mediated by caspase activation.

Journal: Neuroscience letters 20040401

Title: Sphingolipids as bioactive regulators of thrombin generation.

Journal: The Journal of biological chemistry 20040326

Title: Toxicity of glucosylsphingosine (glucopsychosine) to cultured neuronal cells: a model system for assessing neuronal damage in Gaucher disease type 2 and 3.

Journal: Neurobiology of disease 20031201

Title: Lyso-glycosphingolipids mobilize calcium from brain microsomes via multiple mechanisms.

Journal: The Biochemical journal 20031101

Title: Molecular mechanism of psychosine-induced cell death in human oligodendrocyte cell line.

Journal: Journal of neurochemistry 20030901

Title: Substrate reduction intervention by L-cycloserine in twitcher mice (globoid cell leukodystrophy) on a B6;CAST/Ei background.

Journal: Neuroscience letters 20030814

Title: Simultaneous quantification of lyso-neutral glycosphingolipids and neutral glycosphingolipids by N-acetylation with [3H]acetic anhydride.

Journal: Journal of lipid research 20030701

Title: Internal residue loss produced by rearrangement of a novel cationic glycosphingolipid, glyceroplasmalopsychosine, in collision-induced dissociation.

Journal: Journal of mass spectrometry : JMS 20030701

Title: Sphingolipid profile in the CNS of the twitcher (globoid cell leukodystrophy) mouse: a lipidomics approach.

Journal: Cellular and molecular biology (Noisy-le-Grand, France) 20030701

Title: Glucosylceramide and glucosylsphingosine modulate calcium mobilization from brain microsomes via different mechanisms.

Journal: The Journal of biological chemistry 20030627

Title: [Cytokinesis inhibition by glycosphingolipid, psychosine].

Journal: Tanpakushitsu kakusan koso. Protein, nucleic acid, enzyme 20030601

Title: Gaucher disease with parkinsonian manifestations: does glucocerebrosidase deficiency contribute to a vulnerability to parkinsonism?

Journal: Molecular genetics and metabolism 20030601

Title: Control of head morphogenesis in an invertebrate asexually produced larva-like bud ( Cassiopea andromeda; Cnidaria: Scyphozoa).

Journal: Development genes and evolution 20030401

Title: Myoclonic epilepsy in Gaucher disease: genotype-phenotype insights from a rare patient subgroup.

Journal: Pediatric research 20030301

Title: An endogenous peptide is involved in internal control of metamorphosis in the marine invertebrate Cassiopea xamachana (Cnidaria: Scyphozoa).

Journal: Development genes and evolution 20030301

Title: Abnormal expression of the novel epidermal enzyme, glucosylceramide deacylase, and the accumulation of its enzymatic reaction product, glucosylsphingosine, in the skin of patients with atopic dermatitis.

Journal: Laboratory investigation; a journal of technical methods and pathology 20030301

Title: Sphingosylphosphorylcholine is upregulated in the stratum corneum of patients with atopic dermatitis.

Journal: Journal of lipid research 20030101

Title: Glucosylceramide modulates membrane traffic along the endocytic pathway.

Journal: Journal of lipid research 20021101

Title: Conformational studies of a novel cationic glycolipid, glyceroplasmalopsychosine, from bovine brain by NMR spectroscopy.

Journal: Carbohydrate research 20021011

Title: Apoptotic positive cells in Krabbe brain and induction of apoptosis in rat C6 glial cells by psychosine.

Journal: Neuroscience letters 20020920

Title: Glucosylsphingosine accumulation in tissues from patients with Gaucher disease: correlation with phenotype and genotype.

Journal: Molecular genetics and metabolism 20020801

Title: Delayed clinical and pathological signs in twitcher (globoid cell leukodystrophy) mice on a C57BL/6 x CAST/Ei background.

Journal: Neurobiology of disease 20020801

Title: Establishment and characterization of spontaneously immortalized Schwann cells from murine model of globoid cell leukodystrophy (twitcher).

Journal: Journal of neuroscience research 20020601

Title: Galactosylsphingosine (psychosine)-induced expression of cytokine-mediated inducible nitric oxide synthases via AP-1 and C/EBP: implications for Krabbe disease.

Journal: FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20020501

Title: Versatile synthesis of phenoxydiazirine-based fatty acid analogues and photoreactive galactosylceramide.

Journal: Bioorganic & medicinal chemistry letters 20020107

Title: Quantification of galactosylsphingosine in the twitcher mouse using electrospray ionization-tandem mass spectrometry.

Journal: Journal of lipid research 20011201

Title: Saposins (sap) A and C activate the degradation of galactosylsphingosine.

Journal: FEBS letters 20011109

Title: Dramatic phenotypic improvement during pregnancy in a genetic leukodystrophy: estrogen appears to be a critical factor.

Journal: Human molecular genetics 20011101

Title: Suppression of endothelial cell apoptosis by high density lipoproteins (HDL) and HDL-associated lysosphingolipids.

Journal: The Journal of biological chemistry 20010914

Title: Apoptosis of Neuro2a cells induced by lysosphingolipids with naturally occurring stereochemical configurations.

Journal: Journal of lipid research 20010801

Title: Generation of a mouse with low galactocerebrosidase activity by gene targeting: a new model of globoid cell leukodystrophy (Krabbe disease).

Journal: Molecular genetics and metabolism 20010701

Title: Intraventricular administration of recombinant adenovirus to neonatal twitcher mouse leads to clinicopathological improvements.

Journal: Gene therapy 20010701

Title: A one pot synthesis of mono- and di-lactosyl sphingosines.

Journal: Glycoconjugate journal 20010701

Title: A novel plasmal conjugate to glycerol and psychosine ('glyceroplasmalopsychosine'): isolation and characterization from bovine brain white matter.

Journal: The Journal of biological chemistry 20010622

Title: Psychosine is as potent an inducer of cell death as C6-ceramide in cultured fibroblasts and in MOCH-1 cells.

Journal: Neurochemical research 20010601

Title: A mutation in the saposin A domain of the sphingolipid activator protein (prosaposin) gene results in a late-onset, chronic form of globoid cell leukodystrophy in the mouse.

Journal: Human molecular genetics 20010515

Title: Lysosphingolipid receptor-mediated diuresis and natriuresis in anaesthetized rats.

Journal: British journal of pharmacology 20010401

Title: Sphingolipid derivatives modulate intracellular Ca2+ in rat synaptosomes.

Journal: Acta neurobiologiae experimentalis 20010101

Title: Specificity and cross-reactivity of anti-galactocerebroside antibodies.

Journal: Immunological investigations 19950501

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Tags:2238-90-6 Molecular Formula|2238-90-6 MDL|2238-90-6 SMILES|2238-90-6 PSYCHOSINE