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Purity: ≥98%
Lysophosphatidic acid is an endogenous agonist of the lysophospholipid receptors LPA1 and LPA2, a glycerophospholipid signaling ligand molecule and ligand activator for EDG-2, EDG-4, and EDG-7. It inhibits differentiation of neural stem cells (NSCs) into neurons
| Targets |
LPA receptor
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|---|---|
| ln Vitro |
Sodium 1-oleoyl lysophosphatidic acid (0.1-10 μM) can induce and increase the [Ca2+]i potential in rabbit osteoclasts [2]. Sodium 1-oleoyl lysophosphatidic acid (5 μM) induces the contraction of cytoclastic lamellipodia [2].
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| ln Vivo |
The role of lysophosphatidic acid (LPA) in the control of emotional behavior remains to be determined. We analyzed the effects of the central administration of 1-oleoyl-LPA (LPA 18∶1) in rats tested for food consumption and anxiety-like and depression-like behaviors. For this purpose, the elevated plus-maze, open field, Y maze, forced swimming and food intake tests were performed. In addition, c-Fos expression in the dorsal periaqueductal gray matter (DPAG) was also determined. The results revealed that the administration of LPA 18∶1 reduced the time in the open arms of the elevated plus-maze and induced hypolocomotion in the open field, suggesting an anxiogenic-like phenotype. Interestingly, these effects were present following LPA 18∶1 infusion under conditions of novelty but not under habituation conditions. In the forced swimming test, the administration of LPA 18∶1 dose-dependently increased depression-like behavior, as evaluated according to immobility time. LPA treatment induced no effects on feeding. However, the immunohistochemical analysis revealed that LPA 18∶1 increased c-Fos expression in the DPAG. The abundant expression of the LPA1 receptor, one of the main targets for LPA 18∶1, was detected in this brain area, which participates in the control of emotional behavior, using immunocytochemistry. These findings indicate that LPA is a relevant transmitter potentially involved in normal and pathological emotional responses, including anxiety and depression [3].
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| Enzyme Assay |
Real-time RT-PCR Analyses Total RNA was isolated from purified bone marrow-derived osteoclasts using TRIZOL reagent and the RNeasy Mini kit (Qiagen). Primers and probes for murine LPA1 (Edg2, Mm00439145_m1), LPA2 (Edg4, Mm00469562_m1), LPA3 (Edg7, Mm00469694_m1), LPA4 (GPR23, Mm01228533_m1), LPA5 (GPR92, Mm02621109_s1), calcitonin receptor (Calcr, Mm0043227_m1), glyceraldehyde-3-phosphate dehydrogenase (Gapdh, product no. 4308313), and 18 S ribosomal RNA (product no. 4308329) were from Applied Biosystems (Gene Expression Assay). Real-time RT-PCR was performed using TaqMan One-step RT-PCR Master Mix Reagents kit (Applied Biosystems) and the ABI Prism 7900HT Sequence Detector (Applied Biosystems) according to the manufacturer's recommendations. Samples were amplified in triplicate. Dilutions of total RNA obtained from murine bone marrow-derived osteoclasts, small intestine, ovaries, and MC3T3-E1 cells were used to validate relative amplification efficiencies of primer/probe sets. The amounts of mRNA were normalized to levels of 18 S ribosomal RNA in the same samples [2].
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| Cell Assay |
Bone Marrow-derived Osteoclasts [2]
Bone marrow cells from the femurs and tibias of 6–10-week-old male C57Bl/6 mice were used to prepare osteoclasts as described previously (19). After isolation, cells were suspended in α-minimum essential medium supplemented with FBS (10%) and antibiotics (1%) and cultured in T75 tissue culture flasks (15 × 106 cells per flask) with recombinant human macrophage colony-stimulating factor (25 ng/ml). After 24 h, non-adherent cells were removed and resuspended in α-minimum essential medium containing FBS (10%), antibiotics (1%), macrophage colony-stimulating factor (50 ng/ml), and recombinant human RANKL (huRANKL-LZ, a gift from Amgen Inc., 100 ng/ml) and plated at 10 × 104 cells/cm2 in suspension culture dishes (Corning). The resulting cells were cultured for an additional 3 days. Cells were then suspended by incubation for 10 min in Ca2+/Mg2+-free PBS at 4 °C, and osteoclasts were enriched by unit gravity velocity sedimentation through FBS (2 times). RAW-264.7-derived Osteoclast-like Cells[2] The murine leukemic monocyte macrophage cell line RAW 264.7 was obtained from the American Type Culture Collection and maintained in Dulbecco's modified Eagle's medium containing FBS (10%) and antibiotic solution (1%). RAW 264.7 cells were cultured at a density of 1.3 × 104 cells/cm2 and treated with huRANKL-LZ (100 ng/ml) for 4 days to give rise to multinucleated osteoclast-like cells. |
| Animal Protocol |
Given the abundant distribution of the LPA receptors throughout the organism, the i.c.v. administration protocol was used to study the specific role of LPA in the brain, thereby avoiding confounding results derived from potential peripheral effects.[3]
For i.c.v. injections and administration, we used a previously described protocol. Stainless steel guide cannulae aimed at the left or right lateral ventricle were implanted in the rats. The animals were anesthetized with equithesin and placed in a stereotaxic apparatus with the incisor bar set at 5 mm above the interaural line. A guide cannula (7 mm and 23-gauge) was secured to the skull using two stainless steel screws and dental cement, and the opening was closed using 30-gauge obturators. The implantation coordinates were 0.6 mm posterior to bregma, ±2.0 mm lateral, and 3.2 mm below the surface of the skull, according to the rat brain stereotaxic coordinates of Paxinos and Watson. These coordinates placed the cannula 1 mm above the ventricle. After a 7-day postsurgical recovery period, the cannula patency was confirmed through the gravity flow of isotonic saline through an 8-mm long and 30-gauge injector inserted within the guide to 1 mm beyond the tip. This procedure was used to familiarize the animals with the injection technique (sham injection). The obturator was removed from the guide cannula, and an 8 mm injector (30 gauge stainless steel tubing), connected to 70 cm of calibrated polyethylene-10 tubing, was lowered into the ventricle. The tubing was subsequently raised until the flow was initiated, and 5 µL of drug or vehicle solution was infused over a 30–60 s period. The injector remained in the guide cannula for an additional 30 s to facilitate the diffusion of the solution and subsequently was removed. The xstylet was immediately replaced. |
| References |
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| Molecular Formula |
C21H40O7P.NA
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|---|---|
| Molecular Weight |
458.50
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| Exact Mass |
458.24
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| CAS # |
325465-93-8
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| Related CAS # |
1-Oleoyl lysophosphatidic acid; 65528-98-5
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| PubChem CID |
44159357
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| Appearance |
White to off-white solid
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
7
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| Rotatable Bond Count |
21
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| Heavy Atom Count |
30
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| Complexity |
474
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| Defined Atom Stereocenter Count |
1
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| SMILES |
CCCCCCCC/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O)[O-])O.[Na+]
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| InChi Key |
XGRLSUFHELJJAB-JGSYTFBMSA-M
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| InChi Code |
InChI=1S/C21H41O7P.Na/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(23)27-18-20(22)19-28-29(24,25)26;/h9-10,20,22H,2-8,11-19H2,1H3,(H2,24,25,26);/q;+1/p-1/b10-9-;/t20-;/m1./s1
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| Chemical Name |
sodium;[(2R)-2-hydroxy-3-[(Z)-octadec-9-enoyl]oxypropyl] hydrogen phosphate
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| Synonyms |
Lysophosphatidic acid
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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 Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
| 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) |
H2O : ~100 mg/mL (~218.10 mM)
DMSO : ~1.85 mg/mL (~4.03 mM) |
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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 | 2.1810 mL | 10.9051 mL | 21.8103 mL | |
| 5 mM | 0.4362 mL | 2.1810 mL | 4.3621 mL | |
| 10 mM | 0.2181 mL | 1.0905 mL | 2.1810 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.
| NCT Number | Recruitment | interventions | Conditions | Sponsor/Collaborators | Start Date | Phases |
| NCT01766817 | Completed | Drug: BMS-986020 Drug: Placebo matching with BMS-986020 |
Idiopathic Pulmonary Fibrosis | Bristol-Myers Squibb | January 31, 2013 | Phase 2 |
| NCT00986206 | Completed | Diagnostic Test: Biomarker LPA and HE4 |
brca1 Mutation Carrier brca2 Mutation Carrier Ovarian Cancer |
Women and Infants Hospital of Rhode Island |
June 2009 | N/A |
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