| Size | Price | |
|---|---|---|
| 500mg | ||
| 1g | ||
| Other Sizes |
| Targets |
Oleoyl-CoA targets a wide range of proteins, including transcriptional regulators, metabolic enzymes, and transporters. In mycobacteria, it serves as a specific ligand for the transcriptional regulator RaaS (Rv1219c), binding to its C-terminal ligand-binding domain (Kd ≈ 3.65 μM) to regulate DNA binding and thereby control the expression of ATP-dependent efflux pumps. Additionally, Oleoyl-CoA is a substrate for acyl-CoA:cholesterol acyltransferase (ACAT) and microsomal oleoyl-CoA desaturase (Km = 25 μM), while also inhibiting neutral lipase activity. In plants, it mediates the translocation of transcription factor RAP2.12 from the plasma membrane to the nucleus, regulating hypoxic responses.
|
|---|---|
| ln Vitro |
In cell-free systems, Oleoyl-CoA functions as a substrate or modulator for various enzymes. Studies show that it is a specific substrate for microsomal oleoyl-CoA desaturase, with over 40% of radioactive fatty acids converted to linoleic acid when Oleoyl-CoA is used as the substrate, exhibiting an apparent Km of 25 μM. In ACAT activity assays, [1-¹⁴C]-labeled Oleoyl-CoA serves as the acyl donor for assessing cholesterol esterification activity. Furthermore, Oleoyl-CoA inhibits the DNA-binding activity of the transcriptional regulator RaaS, with concentrations ≥15 μM completely abolishing the RaaS-mediated band shift in electrophoretic mobility shift assays (EMSA).
|
| ln Vivo |
In vivo activity is primarily studied via precursor administration or genetic modulation models. In mycobacterial infection models, exogenously added oleic acid (the precursor of Oleoyl-CoA) influences RaaS-mediated bacterial survival by regulating efflux pump gene expression, thereby affecting mycobacterial persistence under non-growing conditions. In plants (Arabidopsis), changes in Oleoyl-CoA levels under hypoxic conditions activate the translocation of transcription factor RAP2.12 from the plasma membrane to the nucleus, regulating the expression of hypoxia-responsive genes. In mammals such as mice, Oleoyl-CoA acts as an endogenous metabolite involved in lipid metabolism regulation in the liver and adipose tissue.
|
| Enzyme Assay |
Binding between Oleoyl-CoA and proteins is typically measured using isothermal titration calorimetry (ITC) or electrophoretic mobility shift assays (EMSA). A typical protocol (using RaaS protein): Purified recombinant RaaS protein is incubated with increasing concentrations of Oleoyl-CoA (0-100 μM) in binding buffer at room temperature. For ITC measurements, Oleoyl-CoA is titrated into the RaaS solution to directly determine binding affinity (Kd = 3.65 ± 0.28 μM) and thermodynamic parameters. For EMSA, constant amounts of RaaS protein are incubated with fluorescently labeled DNA probes and varying concentrations of Oleoyl-CoA, followed by separation on native polyacrylamide gels to observe the disappearance of the protein-DNA complex band.
|
| Cell Assay |
Due to its high polarity and membrane impermeability, cellular assays with Oleoyl-CoA typically utilize permeabilized cell models or indirect studies using its precursor oleic acid. A typical protocol (ACAT activity assay): Microsomes isolated from the livers of cholesterol-fed rats are incubated with [1-¹⁴C]Oleoyl-CoA (as the acyl donor) and cholesterol, and cholesterol ester formation is assessed by radioactivity detection. In mycobacterial studies, bacteria are co-cultured with oleic acid, which is intracellularly converted to Oleoyl-CoA, followed by EMSA or Western Blot analysis of downstream gene expression regulated by RaaS.
|
| Animal Protocol |
Oleoyl-CoA itself is rarely administered directly to animals; studies typically use its precursor oleic acid or genetic knockout models. In a mycobacterial mouse infection model, mycobacteria co-cultured with oleic acid are used to infect mice, followed by assessment of bacterial survival in the lungs and spleen and detection of RaaS-regulated efflux pump gene expression. In metabolic studies, labeled oleic acid can be administered via tail vein injection or gavage, with tissue samples collected at various time points for LC-MS/MS analysis of Oleoyl-CoA and its metabolites. Knockout mouse models (e.g., long-chain acyl-CoA synthetase knockout) can also be used to study the physiological impact of Oleoyl-CoA metabolic dysregulation.
|
| ADME/Pharmacokinetics |
Direct pharmacokinetic parameters for Oleoyl-CoA are limited in the literature as it is an endogenous intracellular metabolite. As a highly polar molecule (polar surface area of 418 Ų) carrying strong negative charges at physiological pH (LogD pH 7.4 ≈ -4.46), it cannot passively diffuse across cell membranes and is primarily synthesized intracellularly and utilized within organelles such as mitochondria and the endoplasmic reticulum. It is unstable in plasma and susceptible to hydrolysis by esterases. Tissue concentrations of Oleoyl-CoA are tightly regulated by fatty acid metabolic status and can change significantly under conditions such as starvation or diabetes. Exogenous Oleoyl-CoA cannot readily enter cells and typically requires delivery systems or the use of its precursor oleic acid for in vivo studies.
|
| Toxicity/Toxicokinetics |
Oleoyl coenzyme A is generally considered safe at normal physiological concentrations as an endogenous metabolite. According to available Material Safety Data Sheets, no detailed toxicological data has been reported for this compound. Suppliers warn that this product is for research use only and not for human or veterinary use. Standard laboratory practices should be followed when handling, avoiding inhalation, ingestion, and skin contact. At high concentrations, it may cause long-lasting harmful effects to aquatic life. Under conditions of metabolic dysregulation (e.g., obesity, diabetes), abnormal accumulation of Oleoyl-CoA may contribute to lipotoxic pathological processes.
|
| References |
| Molecular Formula |
C39H67N7NAO17P3S
|
|---|---|
| Molecular Weight |
1053.96
|
| Exact Mass |
1055.358120
|
| Related CAS # |
Oleoyl coenzyme A lithium; 9(Z)-Octadecenoyl coenzyme A potassium; Oleoyl coenzyme A-13C18 lithium; Oleoyl coenzyme A; Oleoyl Coenzyme A triammonium; 799812-89-8
|
| Appearance |
Typically exists as solids at room temperature
|
| Hydrogen Bond Donor Count |
9
|
| Hydrogen Bond Acceptor Count |
23
|
| Rotatable Bond Count |
35
|
| Heavy Atom Count |
68
|
| Complexity |
1700
|
| Defined Atom Stereocenter Count |
5
|
| SMILES |
[H-].CCCCCCCC/C=C\\CCCCCCCC(=O)SCCNC(=O)CCNC(=O)[C@@H](C(C)(C)COP(=O)(O)OP(=O)(O)OC[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=NC3=C(N=CN=C32)N)O)OP(=O)(O)O)O.[Na+]
|
| InChi Key |
RPBMWHKXOGHJTM-KRDRJGSWSA-N
|
| InChi Code |
InChI=1S/C39H68N7O17P3S.Na.H/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-30(48)67-23-22-41-29(47)20-21-42-37(51)34(50)39(2,3)25-60-66(57,58)63-65(55,56)59-24-28-33(62-64(52,53)54)32(49)38(61-28)46-27-45-31-35(40)43-26-44-36(31)46;;/h11-12,26-28,32-34,38,49-50H,4-10,13-25H2,1-3H3,(H,41,47)(H,42,51)(H,55,56)(H,57,58)(H2,40,43,44)(H2,52,53,54);;/q;+1;-1/b12-11-;;/t28-,32-,33-,34+,38-;;/m1../s1
|
| Chemical Name |
sodium;S-[2-[3-[[(2R)-4-[[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-2-hydroxy-3,3-dimethylbutanoyl]amino]propanoylamino]ethyl] (Z)-octadec-9-enethioate;hydride
|
| Synonyms |
oleoyl-CoA sodium salt); Oleoyl-CoA sodium
|
| 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 | 0.9488 mL | 4.7440 mL | 9.4880 mL | |
| 5 mM | 0.1898 mL | 0.9488 mL | 1.8976 mL | |
| 10 mM | 0.0949 mL | 0.4744 mL | 0.9488 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
