| Size | Price | Stock | Qty |
|---|---|---|---|
| 5mg |
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| Other Sizes |
| Targets |
Arachidonoyl coenzyme A lithium serves as a substrate for multiple lipid-modifying enzymes rather than targeting a single receptor. It is a substrate for lysophosphatidylcholine acyltransferase 3 (LPCAT3), involved in the Lands cycle for phospholipid remodeling. It is also a substrate for glycine N-acyltransferase-like 2 (GLYATL2) for the long-chain N-acylation of glycines in the presence of cytochrome c, as well as for acyltransferases such as lysophosphatidic acid acyltransferase (CGI-58/ABHD5). It functions as a charged membrane-impermeable analog of arachidonic acid.
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| ln Vitro |
In vitro, arachidonoyl coenzyme A lithium is used as a substrate in enzymatic assays to study the activity of acyltransferases and N-acyltransferases. It is incorporated into phosphatidylcholine by lysophosphatidylcholine acyltransferase 3 (LPCAT3) in membrane preparations. The conversion of arachidonoyl-CoA to arachidonoylated lipids can be quantified by liquid chromatography-mass spectrometry (LC-MS) or by using radiolabeled [14C]-arachidonoyl-CoA. In the presence of cytochrome c, it serves as an acyl donor for the synthesis of arachidonoyl amino acids via glycine N-acyltransferase-like 2 (GLYATL2).
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| ln Vivo |
Different regions have different levels of lithium arachidonic acid-CoA synthetic activity. In male Wistar rats, there are no alterations in status epilepticus; however, the synthesis in homogenates and microsomes is greater than that in the cerebellum and brainstem, while the synthesis in synaptic plasma membrane is lower [1].
In vivo, arachidonoyl coenzyme A lithium is used to study arachidonic acid metabolism in cellular and animal models. Because arachidonoyl-CoA is charged and membrane-impermeable, it cannot enter cells directly and is typically delivered by microinjection or by using liposome-based delivery systems, or its effects are studied in permeabilized cell systems. It serves as an important probe for the metabolic fate of arachidonic acid in the arachidonic acid cascade, which is central to the production of eicosanoids (prostaglandins, leukotrienes, thromboxanes) and endocannabinoids. The compound is used in studies of inflammation, platelet aggregation, and neural signaling. |
| Enzyme Assay |
For non-cell-based enzyme assays, a standard protocol for LPCAT3 activity is used. Membrane preparations (50 ug protein) or recombinant LPCAT3 are incubated with 50 uM arachidonoyl coenzyme A lithium and 50 uM lysophosphatidylcholine (18:0 LPC) in assay buffer (100 mM Tris-HCl, pH 7.4, 1 mM DTT, 0.1% Triton X-100) for 30 minutes at 37degC. The reaction is terminated by the addition of chloroform/methanol (2:1). Lipids are extracted, separated by TLC using a solvent system of chloroform/methanol/water (65:25:4), and visualized with iodine vapor. Phosphatidylcholine spots are scraped and analyzed by LC-MS to quantify the incorporation of arachidonic acid. For GLYATL2 assays, the reaction mixture includes 50 uM arachidonoyl CoA, 1 mM glycine, and cytochrome c.
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| Cell Assay |
For in vitro cell-based assays, arachidonoyl coenzyme A lithium is typically used in membrane fractions or permeabilized cells, as the compound is membrane-impermeable. Cells (e.g., RAW 264.7 macrophages) are permeabilized with digitonin (25 ug/mL) for 5 minutes on ice. The permeabilized cells (1 × 10^6 cells per sample) are incubated with 50-100 uM arachidonoyl coenzyme A lithium in intracellular buffer (20 mM HEPES, pH 7.2, 140 mM KCl, 5 mM MgCl2) for 30-60 minutes at 37degC. Lipids are extracted, and the conversion to arachidonoylated phospholipids or N-acyl amino acids is analyzed by LC-MS/MS. Alternatively, radiolabeled [14C]-arachidonoyl-CoA is used for quantitative assays.
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| Animal Protocol |
For in vivo animal studies, arachidonoyl coenzyme A lithium is not typically administered directly because it is charged and membrane-impermeable. However, studies of arachidonic acid metabolism can be conducted by administering [14C]-arachidonic acid, which is then converted intracellularly to arachidonoyl-CoA. In a typical protocol, mice (6-8 weeks old, C57BL/6) receive an intraperitoneal injection of [14C]-arachidonic acid (2 uCi per mouse) in 200 uL of 2% BSA in saline. After 2-24 hours, tissues (liver, brain, kidney) are harvested, and lipids are extracted. The arachidonoyl-CoA fraction is separated by TLC and quantified by liquid scintillation counting to measure the rate of arachidonate activation.
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| ADME/Pharmacokinetics |
Arachidonoyl coenzyme A lithium has a molecular weight of 1059.92 g/mol and a molecular formula of C41H65LiN7O17P3S. The compound is supplied as a powder and should be stored at -20degC. As a charged coenzyme A ester, it is water-soluble and stable in aqueous solutions at pH 5-6 for short periods, but it is susceptible to hydrolysis at neutral to alkaline pH. For in vitro assays, stock solutions (1-10 mM) are prepared in 1 mM sodium citrate buffer (pH 5.0) or 5% acetonitrile in water. For enzyme assays, the working concentration is typically 10-100 uM. The compound should be kept on ice during use and protected from repeated freeze-thaw cycles.
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| Toxicity/Toxicokinetics |
Arachidonoyl coenzyme A lithium is a research-grade reagent and is not intended for human use. No specific toxicity data is available, but as a coenzyme A ester, it is generally considered non-toxic at the concentrations used in in vitro assays (10-100 uM). The compound is handled as a potential irritant; standard chemical safety precautions (gloves, lab coat, safety glasses) should be followed. Avoid inhalation of powder. In vivo, arachidonic acid derivatives can be pro-inflammatory, and high concentrations of arachidonoyl-CoA may affect cellular lipid homeostasis. However, the compound is not administered therapeutically.
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| References | |
| Additional Infomation |
Arachidonoyl coenzyme A lithium is a research reagent and is not a pharmaceutical drug. It has no clinical approval status. This compound is essential for studying the Lands cycle, which is the primary pathway for remodeling membrane phospholipids with arachidonic acid. Arachidonoyl-CoA is the direct precursor for arachidonoyl-containing phospholipids and for the synthesis of N-acyl amides such as N-arachidonoyl glycine. The compound is also used to study the regulation of arachidonic acid release by cytosolic phospholipase A2 (cPLA2). It is an indispensable tool in lipid metabolism research and is strictly for research use only.
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| Molecular Formula |
C41H65N7O17P3S-.LI+
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|---|---|
| Molecular Weight |
1059.92
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| Exact Mass |
1059.35
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| CAS # |
188174-63-2
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| PubChem CID |
23679053
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| Appearance |
Typically exists as solid at room temperature
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| LogP |
6.944
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| Hydrogen Bond Donor Count |
8
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| Hydrogen Bond Acceptor Count |
22
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| Rotatable Bond Count |
34
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| Heavy Atom Count |
70
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| Complexity |
1890
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| Defined Atom Stereocenter Count |
5
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| SMILES |
[Li+].CCCCC/C=C/C/C=C/C/C=C/C/C=C/CCCC(SCCNC(CCNC([C@@H](C(COP(OP(OC[C@H]1O[C@@H](N2C=NC3=C(N=CN=C23)N)[C@H](O)[C@@H]1OP([O-])(O)=O)(O)=O)(O)=O)(C)C)O)=O)=O)=O
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| InChi Key |
PFJKRDANWCBXHE-VKSULDSYSA-M
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| InChi Code |
InChI=1S/C41H66N7O17P3S.Li/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-32(50)69-25-24-43-31(49)22-23-44-39(53)36(52)41(2,3)27-62-68(59,60)65-67(57,58)61-26-30-35(64-66(54,55)56)34(51)40(63-30)48-29-47-33-37(42)45-28-46-38(33)48;/h8-9,11-12,14-15,17-18,28-30,34-36,40,51-52H,4-7,10,13,16,19-27H2,1-3H3,(H,43,49)(H,44,53)(H,57,58)(H,59,60)(H2,42,45,46)(H2,54,55,56);/q;+1/p-1/b9-8+,12-11+,15-14+,18-17+;/t30-,34-,35-,36+,40-;/m1./s1
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| Chemical Name |
lithium;[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-[[hydroxy-[hydroxy-[(3R)-3-hydroxy-4-[[3-[2-[(5E,8E,11E,14E)-icosa-5,8,11,14-tetraenoyl]sulfanylethylamino]-3-oxopropyl]amino]-2,2-dimethyl-4-oxobutoxy]phosphoryl]oxyphosphoryl]oxymethyl]oxolan-3-yl] hydrogen phosphate
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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 | 0.9435 mL | 4.7173 mL | 9.4347 mL | |
| 5 mM | 0.1887 mL | 0.9435 mL | 1.8869 mL | |
| 10 mM | 0.0943 mL | 0.4717 mL | 0.9435 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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