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Psychosine-d7

Psychosine-d7 is the deuterium labelled form of Psychosine.
Psychosine-d7
Psychosine-d7 Chemical Structure CAS No.: 2315262-31-6
Product category: New3
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
1mg
Other Sizes

Other Forms of Psychosine-d7:

  • Psychosine
Official Supplier of:
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Top Publications Citing lnvivochem Products
Product Description
Psychosine-d7 is the deuterium labelled form of Psychosine. Psychosine is a substrate of the galactocerebrosidase (GALC) enzyme and a potential biomarker for Krabbe's disease. Psychosine is a highly cytotoxic lipid that induces cell death in a variety of cell types, in part through apoptosis. Psychosine is also a PKC inhibitor.
Psychosine-d7 (galactosylsphingosine-d7) is the deuterium-labeled form of psychosine (galactosylsphingosine), a glycosphingolipid consisting of galactose β-linked to sphingosine, with seven deuterium atoms on the sphingosine backbone. Psychosine is the deacylated form of galactosylceramide and is a substrate of galactocerebrosidase (GALC); in Krabbe disease (globoid cell leukodystrophy), GALC deficiency causes psychosine accumulation, which is highly cytotoxic to oligodendrocytes and Schwann cells and is a validated biomarker for disease progression and treatment monitoring. The d7 form is a dedicated isotope-dilution internal standard for psychosine quantification by LC-MS/MS.
Biological Activity I Assay Protocols (From Reference)
Targets
Isotope-labeled galactosylsphingosine; no intrinsic receptor or enzyme agonist activity. Endogenous psychosine is a cytotoxic lipid whose accumulation in Krabbe disease is thought to mediate oligodendrocyte death and demyelination; it is also a substrate for GALC. The deuterated standard is used as an analytical surrogate and does not modulate GALC activity or psychosine-mediated cytotoxicity.
ln Vitro
Drug compounds have included stable heavy isotopes of carbon, hydrogen, and other elements, mostly as quantitative tracers while the drugs were being developed. Because deuteration may have an effect on a drug's pharmacokinetics and metabolic properties, it is a matter for concern [3].
The d7-psychosine standard shows no intrinsic bioactivity and is not used for potency screening. Endogenous psychosine is a low-abundance cytotoxic lipid that requires a structurally matched internal standard for accurate quantification; the d7 form co-elutes with the analyte and corrects for extraction recovery, ionization efficiency, and matrix effects in dried blood spots, plasma, and tissue.
ln Vivo
No intrinsic in vivo pharmacological activity has been reported for the deuterated standard. Endogenous psychosine accumulates in the central and peripheral nervous systems of patients and animal models with Krabbe disease and is a pharmacodynamic biomarker for GALC enzyme replacement and gene therapy. The d7 standard supports in vivo quantification of psychosine in blood and tissue and enables monitoring of treatment response.
Enzyme Assay
LC-MS/MS psychosine quantification: add Psychosine-d7 to the sample (e.g., dried blood spot, plasma, or tissue homogenate) before protein precipitation or lipid extraction; extract with methanol or methanol/water; separate on a reversed-phase C18 column or a HILIC column; monitor the specific m/z transition of the d7 standard (e.g., m/z 467.4→289.3) and the corresponding unlabeled psychosine transition (e.g., m/z 460.4→282.3). Quantification is by isotope-dilution calibration using peak-area ratios.
Cell Assay
Cell-based psychosine cytotoxicity assay: culture oligodendrocyte-lineage cells or Schwann cells, treat with serially diluted psychosine in the presence or absence of GALC, and measure cell viability by MTT or LDH release; quantify psychosine levels in cells and medium by LC-MS/MS using the d7 standard. The assay is used to study psychosine-mediated cytotoxicity and the protective effect of GALC.
Animal Protocol
In vivo biomarker analysis in Krabbe disease models: collect dried blood spots or tissue (brain, sciatic nerve) from GALC-deficient mice or patients, add Psychosine-d7 as internal standard, extract psychosine, and quantify by LC-MS/MS. The data are used to correlate psychosine levels with disease severity and to monitor the pharmacodynamic effect of enzyme replacement or gene therapy.
References

[1]. Psychosine, a marker of Krabbe phenotype and treatment effect. Mol Genet Metab. 2017 Jul;121(3):271-278.

[2]. Psychosine, the cytotoxic sphingolipid that accumulates in globoid cell leukodystrophy, alters membrane architecture. J Lipid Res.2013 Dec;54(12):3303-11.

[3]. Impact of Deuterium Substitution on the Pharmacokinetics of Pharmaceuticals. Ann Pharmacother. 2019;53(2):211-223.

These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C24H40D7NO7
Molecular Weight
468.68
Exact Mass
468.379
CAS #
2315262-31-6
Related CAS #
Psychosine;2238-90-6
PubChem CID
164516806
Appearance
White to off-white solid
LogP
3.7
Hydrogen Bond Donor Count
6
Hydrogen Bond Acceptor Count
8
Rotatable Bond Count
18
Heavy Atom Count
32
Complexity
479
Defined Atom Stereocenter Count
7
SMILES
[2H]C([2H])([2H])C([2H])([2H])C([2H])([2H])CCCCCCCCCC/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
InChi Key
HHJTWTPUPVQKNA-RMWPRCMXSA-N
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/i1D3,2D2,3D2
Chemical Name
(2R,3R,4S,5R,6R)-2-[(E,2S,3R)-2-amino-16,16,17,17,18,18,18-heptadeuterio-3-hydroxyoctadec-4-enoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
HS Tariff Code
2934.99.9001
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)
Solubility Data
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
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
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)
*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).
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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)]
*Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300:Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL 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).
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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders


Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.1337 mL 10.6683 mL 21.3365 mL
5 mM 0.4267 mL 2.1337 mL 4.2673 mL
10 mM 0.2134 mL 1.0668 mL 2.1337 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.

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What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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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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