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| 1mg |
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| 5mg |
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| Targets |
Psychosine has multiple mechanisms of action. It is a protein kinase C (PKC) inhibitor and is a substrate for the enzyme galactosylceramide cerebrosidase (GALC). It inhibits metabotropic alpha 1-adrenergic receptor signaling-induced phospholipase C activation in rat brain astrocytes. Psychosine also potentiates LPS-induced production of inflammatory cytokines, decreases the mitochondrial membrane potential, and induces cell death in mouse astrocytes.
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| ln Vitro |
Psychosine is a GALC enzyme substrate that helps diagnose and treat high-risk newborns identified by newborn baby care (NBS) [1]. Psychosine has pleiotropic effects, which include the malfunctioning of numerous cellular nutrients [2].
In vitro, psychosine acts as a PKC inhibitor and a substrate for GALC. It potentiates LPS-induced production of inflammatory cytokines and decreases the mitochondrial membrane potential, inducing cell death in mouse astrocytes. It has strong cytotoxicity and can induce various types of cell death. Psychosine also displays neuroprotective effects against quisqualate. |
| ln Vivo |
In vivo, psychosine is the toxic metabolite that accumulates in Krabbe disease due to GALC deficiency. It is a potential biomarker for diagnosing and treating high-risk newborns identified by newborn screening. Its accumulation leads to the malfunctioning of numerous cellular processes and is responsible for the pathophysiology of the disease.
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| Enzyme Assay |
Non-cellular enzyme assays for psychosine involve assessing its role as a substrate for galactosylceramide cerebrosidase (GALC). Purified GALC enzyme is incubated with a fluorescent or radiolabeled psychosine substrate in the presence of varying concentrations of the compound. The release of the fluorescent or radiolabeled product is measured, and the kinetic parameters (Km, Vmax) for GALC-mediated hydrolysis are determined.
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| Cell Assay |
Cell Viability Assay [2]
Cell Types: Oligodendrocytes, M03.13 Tested Concentrations: 10, 20 and 40 μM Incubation Duration: 24 hrs (hours) Experimental Results: Cell death occurs, at least in part, by apoptosis. In vitro cellular assays for psychosine involve treating cells, such as oligodendrocytes, astrocytes, or immune cells, with the compound and measuring its effects on cell viability, inflammatory cytokine production, and mitochondrial function. Cell viability is measured using MTT or CellTiter-Glo® assays. Cytokine production is measured by ELISA. Mitochondrial membrane potential is assessed using fluorescent dyes such as JC-1. |
| Animal Protocol |
In vivo animal experiments with psychosine are conducted in the twitcher mouse model of Krabbe disease, where the compound accumulates due to GALC deficiency. The levels of psychosine in the brain and other tissues are measured by LC-MS/MS. The effects of potential therapies on psychosine accumulation and disease progression are evaluated.
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| ADME/Pharmacokinetics |
Psychosine has a molecular weight of 461.63 and a molecular formula of C₂₄H₄₇NO₇. It is a solid powder with a purity of ≥95%. The compound is soluble in DMSO and other organic solvents. It is typically stored at -20°C, protected from light and moisture. The compound is stable under recommended storage conditions.
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| Toxicity/Toxicokinetics |
Psychosine is a research compound for laboratory use only and is not intended for human therapeutic or diagnostic use. It is a highly cytotoxic compound that induces cell death in various cell types. Standard laboratory safety precautions should be followed when handling the compound. It may cause skin, eye, and respiratory irritation. Appropriate personal protective equipment should be used.
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| References | |
| Additional Infomation |
Psychosine are glycosylsphingosine, composed of a sphingosine molecule with a β-D-galactose residue linked at the 1-position. They are a human metabolite functionally related to sphingosine-4-ene and sphingosine. They are the conjugate base of Psychosine (1+). Psychosine have been reported to exist in Homo sapiens, and relevant data exist. They are intermediates in the biosynthesis of cerebrosides. They are generated from the reaction of sphingosine with UDP-galactose, and then react with fatty acid-coenzyme A to form cerebrosides.
Psychosine (Galactosylsphingosine; CAS 2238-90-6) is a cationic lysosphingolipid and a substrate for galactosylceramide cerebrosidase (GALC). It is a PKC inhibitor and a potential biomarker for Krabbe disease. Psychosine is highly cytotoxic and induces cell death. It is a valuable research tool for studying Krabbe disease and sphingolipid metabolism, available from various commercial suppliers. |
| Molecular Formula |
C24H47NO7
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|---|---|
| Molecular Weight |
461.64
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| Exact Mass |
461.335
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| CAS # |
2238-90-6
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| Related CAS # |
Psychosine-d5;2260670-12-8;Psychosine-d7;2315262-31-6
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| PubChem CID |
5280458
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| Appearance |
White to off-white solid powder
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| Density |
1.14 g/cm3
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| Boiling Point |
664.3ºC
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| Flash Point |
355.6ºC
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| Vapour Pressure |
1.77E-20mmHg at 25°C
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| Index of Refraction |
1.535
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| LogP |
2.448
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| Hydrogen Bond Donor Count |
6
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| Hydrogen Bond Acceptor Count |
8
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| Rotatable Bond Count |
18
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| Heavy Atom Count |
32
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| Complexity |
479
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| Defined Atom Stereocenter Count |
7
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| SMILES |
CCCCCCCCCCCCC/C=C/[C@H]([C@H](CO[C@H]1[C@@H]([C@H]([C@H]([C@H](O1)CO)O)O)O)N)O
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| InChi Key |
HHJTWTPUPVQKNA-PIIMIWFASA-N
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| InChi Code |
InChI=1S/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+/m0/s1
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| Chemical Name |
(2R,3R,4S,5R,6R)-2-[(E,2S,3R)-2-amino-3-hydroxyoctadec-4-enoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
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| Synonyms |
Sphingosine galactoside; Galactosylsphingosine; Psychosine
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.1662 mL | 10.8310 mL | 21.6619 mL | |
| 5 mM | 0.4332 mL | 2.1662 mL | 4.3324 mL | |
| 10 mM | 0.2166 mL | 1.0831 mL | 2.1662 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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