| Size | Price | Stock | Qty |
|---|---|---|---|
| 1mg |
|
||
| Other Sizes |
| Targets |
S1PR1 19.3 nM (EC50, human) S1PR3 131.8 nM (EC50, human) S1PR2 313.3 nM (EC50, human)
Targets S1P receptors 1, 2, and 3 (S1PR1, S1PR2, S1PR3) as an agonist, with greatest potency at hS1P1 (EC50=19.3 nM), followed by hS1P3 (131.8 nM) and hS1P2 (313.3 nM). It binds to these GPCRs and activates downstream Gi, Gq, and G12/13 signaling pathways depending on the receptor subtype expressed in the target cell. |
|---|---|
| ln Vitro |
As a potent S1P receptor agonist, L-threo Lysosphingomyelin activates S1P1-mediated Gi signaling pathways, leading to inhibition of adenylate cyclase, activation of ERK1/2, and enhancement of endothelial barrier integrity. At higher concentrations, it also activates S1P2 and S1P3, which mediate Rho activation, cell contraction, and inflammatory responses. It is a valuable tool for studying S1P receptor pharmacology.
|
| ln Vivo |
Detailed in vivo activity data for this specific sphingolipid isomer is limited. As a bioactive endogenous sphingolipid and potent S1P receptor agonist, it is expected to reproduce many of the in vivo effects of S1P, including modulation of lymphocyte trafficking, vascular permeability, and cardiovascular function. However, no published animal efficacy studies with this specific compound are publicly available.
|
| Enzyme Assay |
Cell-free GTPgammaS binding assays are performed using membranes prepared from CHO cells stably expressing human S1P1, S1P2, or S1P3. Membranes (10 microg/well) are incubated in assay buffer (20 mM HEPES, pH 7.4, 100 mM NaCl, 5 mM MgCl2, 0.1% BSA) containing 10 microM GDP, 0.1 nM [3⁵S]GTPgammaS, and increasing concentrations of L-threo Lysosphingomyelin (0.1 nM-10 microM) for 60 min at 30degC. Bound radioactivity is separated by filtration through GF/B filters and quantified by scintillation counting to determine EC50 values for each S1P receptor subtype.
|
| Cell Assay |
CHO-K1 cells stably expressing human S1P1, S1P2, or S1P3 are loaded with Fluo-4 AM calcium indicator (4 microM) in HBSS buffer with 20 mM HEPES for 30 min at 37degC. Cells are washed and stimulated with increasing concentrations of L-threo Lysosphingomyelin (0.1 nM-10 microM). Calcium flux (Ex/Em=494/516 nm) is measured using a FLIPR or fluorescence plate reader to determine functional agonist EC50 values. Human S1P1 activation is most potent (19.3 nM).
|
| Animal Protocol |
No specific animal studies are reported. As an endogenous sphingolipid agonist of S1P receptors, it could be studied in mouse models of inflammation, vascular permeability, and lymphocyte trafficking. Standard in vivo studies would involve intravenous or intraperitoneal administration at doses (0.1-10 mg/kg) based on the potency profile. However, this compound is primarily used for in vitro mechanistic studies of S1P receptor activation.
|
| ADME/Pharmacokinetics |
Detailed PK data for L-threo Lysosphingomyelin is not publicly available. As an endogenous sphingolipid, its metabolism involves phosphorylation, dephosphorylation, and degradation by S1P lyase. In vivo, it would be expected to have a relatively short half-life due to rapid metabolism and clearance. It is typically stored at -20degC as a solid powder and is soluble in DMSO and ethanol. Molecular formula: C23H4₉N2O₅P, MW 464.62.
|
| Toxicity/Toxicokinetics |
No toxicity data is publicly available for L-threo Lysosphingomyelin. As an endogenous bioactive sphingolipid and S1P receptor agonist, it may have potential toxicities at high doses, including cardiovascular effects (bradycardia, hypotension), pulmonary edema due to increased vascular permeability (via S1P1/S1P3 activation), and modulation of lymphocyte trafficking. However, as a research reagent, it is used at relatively low concentrations.
|
| References | |
| Additional Infomation |
L-threo Lysosphingomyelin (d18:1) is a research chemical, not approved for clinical use. It is an endogenous bioactive sphingolipid that serves as an isomer of lysosphingomyelin and a potent agonist of S1P receptors 1-3. It is a useful tool compound for studying S1P signaling pathways, particularly for dissecting the relative contributions of S1P1, S1P2, and S1P3 in various cellular contexts.
|
| Molecular Formula |
C23H49N2O5P
|
|---|---|
| Molecular Weight |
464.62
|
| Exact Mass |
464.337
|
| CAS # |
105615-55-2
|
| PubChem CID |
137700280
|
| Appearance |
White to off-white solid powder
|
| LogP |
2.66
|
| Hydrogen Bond Donor Count |
2
|
| Hydrogen Bond Acceptor Count |
6
|
| Rotatable Bond Count |
21
|
| Heavy Atom Count |
31
|
| Complexity |
489
|
| Defined Atom Stereocenter Count |
2
|
| SMILES |
CCCCCCCCCCCCC/C=C/[C@@H]([C@H](COP(=O)([O-])OCC[N+](C)(C)C)N)O
|
| InChi Key |
JLVSPVFPBBFMBE-ZRPIXQTESA-N
|
| InChi Code |
InChI=1S/C23H49N2O5P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-23(26)22(24)21-30-31(27,28)29-20-19-25(2,3)4/h17-18,22-23,26H,5-16,19-21,24H2,1-4H3/b18-17+/t22-,23-/m0/s1
|
| Chemical Name |
[(E,2S,3S)-2-amino-3-hydroxyoctadec-4-enyl] 2-(trimethylazaniumyl)ethyl phosphate
|
| 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 (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
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 | 2.1523 mL | 10.7615 mL | 21.5230 mL | |
| 5 mM | 0.4305 mL | 2.1523 mL | 4.3046 mL | |
| 10 mM | 0.2152 mL | 1.0761 mL | 2.1523 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.
Products are for research use only; We do not sell to patients
Copyright 2020 InvivoChem LLC | All Rights Reserved
