| Size | Price | |
|---|---|---|
| 500mg | ||
| 1g | ||
| Other Sizes |
| Targets |
Acceptor oxidoreductase; The primary targets of Phenylacetyl CoA include choline acetyltransferase (ChAT) and pyruvate carboxylase (PC). It acts as an inhibitor of choline acetyltransferase via competitive binding with acetyl-CoA. In metabolic regulation, it serves as a substrate for phenylacetyl-CoA: L-glutamine N-acetyltransferase, which catalyzes the synthesis of phenylacetylglutamine, providing an alternative pathway for nitrogen excretion. Additionally, in bacteria, it is a substrate for phenylacetyl-CoA: acceptor oxidoreductase, a membrane-bound molybdenum-iron-sulfur enzyme.
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|---|---|
| ln Vitro |
Phenylacetic acids are common intermediates in the microbial metabolism of various aromatic substrates including phenylalanine. In the denitrifying bacterium Thauera aromatica phenylacetate is oxidized, under anoxic conditions, to the common intermediate benzoyl-CoA via the intermediates phenylacetyl-CoA and phenylglyoxylate (benzoylformate). The enzyme that catalyzes the four-electron oxidation of phenylacetyl-CoA has been purified from this bacterium and studied. The enzyme preparation catalyzes the reaction phenylacetyl-CoA + 2 quinone + 2 H2O --> phenylglyoxylate + 2 quinone H2 + CoASH. Phenylacetyl-CoA:acceptor oxidoreductase is a membrane-bound molybdenum-iron-sulfur protein. The purest preparations contained three subunits of 93, 27, and 26 kDa. Ubiquinone is most likely to act as the electron acceptor, and the oxygen atom introduced into the product is derived from water. The protein preparations contained 0.66 mol Mo, 30 mol Fe, and 25 mol acid-labile sulfur per mol of native enzyme, assuming a native molecular mass of 280 kDa. Phenylglyoxylyl-CoA, but not mandelyl-CoA, was observed as a free intermediate. All enzyme preparations also catalyzed the subsequent hydrolytic release of coenzyme A from phenylglyoxylyl-CoA but not from phenylacetyl-CoA. The enzyme is reversibly inactivated by a low concentration of cyanide, but is remarkably stable with respect to oxygen. This new member of the molybdoproteins represents the first example of an enzyme which catalyzes the alpha-oxidation of a CoA-activated carboxylic acid without utilizing molecular oxygen [1].
In cell-free systems, Phenylacetyl CoA serves as an acyl donor for acyltransferase activity assays. In vitro studies demonstrate that Phenylacetyl CoA is a potent inhibitor of choline acetyltransferase (ChAT), exhibiting competitive inhibition with respect to acetyl-CoA with a Ki of 3.1 × 10⁻⁷ M; in contrast, millimolar concentrations of its precursor phenylacetic acid are required to inhibit the enzyme. Furthermore, Phenylacetyl CoA concentration-dependently inhibits purified pyruvate carboxylase activity, thereby suppressing gluconeogenesis. |
| ln Vivo |
In vivo studies demonstrate that phenylacetic acid (the precursor of Phenylacetyl CoA) suppresses gluconeogenesis. In both normal and streptozocin-induced diabetic rats, intravenous administration of phenylpropionic acid (a phenylacetic acid analog) significantly decreased blood glucose levels (normal rats: 110 ± 12 to 66 ± 11 mg/dL; diabetic rats: 295 ± 14 to 225 ± 12 mg/dL). This glucose-lowering effect is attributed to the inhibition of pyruvate carboxylase by Phenylacetyl CoA in the liver, thereby reducing de novo glucose synthesis. In clinical applications, phenylacetic acid is converted to Phenylacetyl CoA, which subsequently conjugates with glutamine to form phenylacetylglutamine, serving as an ammonia scavenger for patients with urea cycle disorders.
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| Enzyme Assay |
Phenylacetyl CoA can be used as a substrate in radiometric acyltransferase assays. A typical protocol (using penicillin acyltransferase) involves incubating ¹⁴C-labeled Phenylacetyl CoA, the substrate 6-aminopenicillanic acid (6-APA), and the purified enzyme in Tris-HCl buffer (pH 7.5) at 37°C. The product [¹⁴C]-benzylpenicillin is extracted using organic solvents, and radioactivity is quantified by liquid scintillation counting to determine enzyme activity. Alternatively, RP-HPLC with detection at 260 nm is used to monitor the conversion of Phenylacetyl CoA to products such as oxepin-CoA.
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| Cell Assay |
In cellular assays, Phenylacetyl CoA is used to study gluconeogenesis regulation. A typical protocol involves isolating rat hepatocytes and suspending them in Krebs-Henseleit buffer. Cells are incubated with phenylacetic acid (4 mM), which is naturally converted to Phenylacetyl CoA intracellularly. Gluconeogenic activity is assessed by measuring the incorporation of [¹⁴C]-bicarbonate into glucose or the rate of pyruvate carboxylation. Studies show that phenylacetic acid (mediated by Phenylacetyl CoA) inhibits gluconeogenesis from 10 mM lactate/1 mM pyruvate by 39% (P < 0.05).
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| Animal Protocol |
In animal models, Phenylacetyl CoA is typically studied indirectly by administering its precursor, phenylacetic acid or phenylbutyrate. A typical protocol (rat gluconeogenesis suppression model): Male Sprague-Dawley rats (200-250 g) are fasted overnight to deplete liver glycogen. Phenylpropionic acid (a phenylacetic acid analog) is administered via jugular vein catheter as a 20 mg bolus followed by continuous infusion at 1 mg/min. Blood samples are collected from the tail vein at various time points, and glucose levels are measured by glucose oxidase method. At the endpoint, animals are euthanized, and liver tissues are collected for glycogen content and pyruvate carboxylase activity assays.
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| ADME/Pharmacokinetics |
Direct pharmacokinetic parameters for Phenylacetyl CoA itself as an intracellular transient intermediate are limited in the literature. However, pharmacokinetic data for its precursor, phenylacetic acid, have been reported: the time to reach maximum plasma concentration (Tmax) is approximately 3.7 hours, maximum plasma concentration (Cmax) is 205.8 μM, plasma protein binding is approximately 51%, and elimination half-life (t½) is 1.15 hours. Phenylacetyl CoA is generated in vivo from phenylacetic acid via acyl-CoA synthetase and is rapidly metabolized, primarily conjugating with glutamine to form phenylacetylglutamine for renal excretion.
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| Toxicity/Toxicokinetics |
Phenylacetyl CoA is non-toxic at normal physiological concentrations as an endogenous metabolite, but its precursor phenylacetic acid exhibits neurotoxicity at high concentrations. Studies suggest that the neurotoxicity of phenylacetate may be mediated by its metabolite Phenylacetyl CoA: Phenylacetyl CoA reduces acetylcholine synthesis by inhibiting choline acetyltransferase (ChAT, Ki = 3.1 × 10⁻⁷ M), which may represent a mechanism underlying the neurological damage in phenylketonuria (PKU) patients. In clinical use, when phenylacetic acid is used as an ammonia scavenger, blood concentrations must be monitored to avoid toxicity. When used as a chemical reagent, standard laboratory practices should be followed.
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| References | |
| Additional Infomation |
Phenylacetyl-CoA is an acyl-CoA enzyme formed by the condensation of the sulfhydryl group of CoA and the carboxyl group of phenylacetic acid. It is a metabolite, found in both E. coli and mice. Its function is related to phenylacetic acid and acetyl-CoA. It is the conjugate acid of phenylacetyl-CoA (4-). Phenylacetyl-CoA is a metabolite found or produced in E. coli (K12 strain, MG1655 strain). There are reports of the presence of phenylacetyl-CoA in humans, and relevant data are available.
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| Molecular Formula |
C29H42N7O17P3S
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|---|---|
| Molecular Weight |
885.6668
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| Exact Mass |
885.157
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| CAS # |
7532-39-0
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| Related CAS # |
108321-26-2
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| PubChem CID |
165620
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| Appearance |
Typically exists as solid at room temperature
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| LogP |
1.27
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| Hydrogen Bond Donor Count |
9
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| Hydrogen Bond Acceptor Count |
22
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| Rotatable Bond Count |
22
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| Heavy Atom Count |
57
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| Complexity |
1530
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| Defined Atom Stereocenter Count |
5
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| SMILES |
S(C(C([H])([H])C1C([H])=C([H])C([H])=C([H])C=1[H])=O)C([H])([H])C([H])([H])N([H])C(C([H])([H])C([H])([H])N([H])C([C@@]([H])(C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])OP(=O)(O[H])OP(=O)(O[H])OC([H])([H])[C@]1([H])[C@]([H])([C@]([H])([C@]([H])(N2C([H])=NC3=C(N([H])[H])N=C([H])N=C23)O1)O[H])OP(=O)(O[H])O[H])O[H])=O)=O
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| InChi Key |
ZIGIFDRJFZYEEQ-CECATXLMSA-N
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| InChi Code |
InChI=1S/C29H42N7O17P3S/c1-29(2,24(40)27(41)32-9-8-19(37)31-10-11-57-20(38)12-17-6-4-3-5-7-17)14-50-56(47,48)53-55(45,46)49-13-18-23(52-54(42,43)44)22(39)28(51-18)36-16-35-21-25(30)33-15-34-26(21)36/h3-7,15-16,18,22-24,28,39-40H,8-14H2,1-2H3,(H,31,37)(H,32,41)(H,45,46)(H,47,48)(H2,30,33,34)(H2,42,43,44)/t18-,22-,23-,24+,28-/m1/s1
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| Chemical Name |
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] 2-phenylethanethioate
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| Synonyms |
phenylacetyl-CoA; Phenylacetyl CoA; 7532-39-0; Phenylacetyl coenzyme A; Phenylacetyl-coenzyme A; Coenzyme A, S-(benzeneacetate); CNJ7ZS9RVB; 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] 2-phenylethanethioate;
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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 | 1.1291 mL | 5.6454 mL | 11.2909 mL | |
| 5 mM | 0.2258 mL | 1.1291 mL | 2.2582 mL | |
| 10 mM | 0.1129 mL | 0.5645 mL | 1.1291 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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