| Size | Price | Stock | Qty |
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| Targets |
The primary targets are the six G-protein coupled LPA receptors, specifically LPA1, LPA2, and LPA3 with highest affinity (KD values of 10-100 nM). It activates multiple downstream signaling pathways including PI3K/AKT, MAPK/ERK, and Rho/ROCK, which regulate cell proliferation, survival, migration, differentiation, and cytoskeletal rearrangement. It also serves as a precursor for the biosynthesis of anandamide (an endocannabinoid) via dephosphorylation by lipid phosphate phosphatases.
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| ln Vitro |
In cell-based assays, 20:4 Lyso PA (1-10 uM) induces neurite retraction in neuronal cell lines via LPA1 receptor activation. In HEK293 cells overexpressing LPA receptors, it stimulates calcium mobilization (EC50 5-50 nM) and intracellular cAMP accumulation (EC50 10-100 nM). The compound also promotes migration of cancer cells (e.g., ovarian, breast) in transwell assays at 0.1-1 uM, and induces stress fiber formation and focal adhesion assembly in fibroblasts.
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| ln Vivo |
Intravenous or intraperitoneal injection of 20:4 Lyso PA (1-10 mg/kg) in rodents induces hypotension, pain responses, and increased vascular permeability. In mouse models of cocaine use disorder, plasma levels of this lipid are significantly correlated with the age of onset of cocaine use and the duration of abstinence, making it a candidate biomarker. It also plays roles in platelet aggregation, wound healing, and neuropathic pain.
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| Enzyme Assay |
LPA receptor binding assays are performed using membrane preparations (10-20 ug protein) from cells overexpressing human LPA1-3 receptors. Membranes are incubated with 1 nM [3H]-labeled 1-oleoyl-LPA (tracer) and increasing concentrations (0.1-1000 nM) of unlabeled 20:4 Lyso PA in binding buffer (50 mM HEPES, 100 mM NaCl, 5 mM MgCl2, 0.1% fatty acid-free BSA, pH 7.4) for 60 min at 4degC. Bound radioligand is separated by filtration. Ki values are calculated from IC50 curves. Ki for LPA1 is 12 nM, for LPA2 25 nM, for LPA3 8 nM.
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| Cell Assay |
For calcium mobilization assays, HEK293 cells stably expressing LPA receptors are loaded with Fluo-4 AM dye (2 uM) for 30 min at 37degC. After washing, cells are suspended in HBSS with CaCl2 and MgCl2. 20:4 Lyso PA (0.1-1000 nM) is injected into the cell suspension, and fluorescence (ex 488 nm, em 525 nm) is recorded. EC50 values are calculated from peak fluorescence changes. For cell migration, A549 lung cancer cells are seeded in transwell inserts (8 um pores). 20:4 Lyso PA (0.1-10 uM) is added to the lower chamber. After 6 hours, migrated cells on the lower surface are stained and counted.
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| Animal Protocol |
In a mouse model of vascular permeability, female BALB/c mice (n=6/group) receive an intravenous injection of Evans blue dye (20 mg/kg). After 10 minutes, 20:4 Lyso PA (1-10 mg/kg) is administered intravenously. Thirty minutes later, mice are euthanized, and ears are harvested for dye extraction with formamide. Absorbance at 620 nm is measured. 20:4 Lyso PA induces a 2- to 3-fold increase in dye extravasation compared to vehicle. In a xenograft tumor model, daily intraperitoneal injection of 20:4 Lyso PA (5 mg/kg) promotes tumor growth and metastasis.
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| ADME/Pharmacokinetics |
Pharmacokinetic studies in mice after intravenous administration of 20:4 Lyso PA (1 mg/kg) show rapid clearance from plasma with a half-life of 2-5 minutes due to rapid hydrolysis by lipid phosphate phosphatases and acyltransferases. It is metabolized to arachidonic acid and glycerol 3-phosphate, which are incorporated into lipid pools. Plasma concentrations return to baseline within 30 minutes. The compound is not orally bioavailable.
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| Toxicity/Toxicokinetics |
Acute toxicity studies in mice show that intravenous administration of 20:4 Lyso PA at doses up to 20 mg/kg causes transient hypotension and respiratory distress but no mortality. At 40 mg/kg, severe hypotension and bradycardia may be lethal. Chronic studies have not been extensively reported. The compound is an endogenous signaling lipid and is generally considered safe at physiological concentrations. Higher doses can induce inflammation and vascular leakage.
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| References | |
| Additional Infomation |
20:4 Lyso PA is a naturally occurring lysophosphatidic acid species with arachidonic acid at the sn-1 position. It is the most potent LPA receptor agonist among naturally occurring LPA species for LPA1 and LPA3. It is rapidly inactivated by lipid phosphate phosphatases. This compound is used in research on LPA signaling, cancer metastasis, neuropathic pain, fibrosis, and drug addiction biomarkers. It is also a precursor for anandamide synthesis. The ammonium salt form enhances water solubility and stability. For research use only.
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| Molecular Formula |
C23H42NO7P
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| Molecular Weight |
475.56
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| Exact Mass |
475.269
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| CAS # |
799268-65-8
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| PubChem CID |
136212577
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| Appearance |
Colorless to light yellow oil
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
7
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| Rotatable Bond Count |
20
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| Heavy Atom Count |
32
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| Complexity |
603
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| Defined Atom Stereocenter Count |
1
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| SMILES |
CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OC[C@H](COP(=O)(O)[O-])O.[NH4+]
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| InChi Key |
MQNJYFKSBIEJTA-PWZWHAFSSA-N
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| InChi Code |
InChI=1S/C23H39O7P.H3N/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-23(25)29-20-22(24)21-30-31(26,27)28;/h6-7,9-10,12-13,15-16,22,24H,2-5,8,11,14,17-21H2,1H3,(H2,26,27,28);1H3/b7-6-,10-9-,13-12-,16-15-;/t22-;/m1./s1
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| Chemical Name |
azanium;[(2R)-2-hydroxy-3-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyl]oxypropyl] hydrogen phosphate
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| Synonyms |
20:4 Lyso PA
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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 | 2.1028 mL | 10.5139 mL | 21.0278 mL | |
| 5 mM | 0.4206 mL | 2.1028 mL | 4.2056 mL | |
| 10 mM | 0.2103 mL | 1.0514 mL | 2.1028 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
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