| Size | Price | Stock | Qty |
|---|---|---|---|
| 1mg |
|
||
| 5mg |
|
||
| Other Sizes |
| Targets |
Phenylacetylglutamine-D5 does not have a specific pharmacological target itself, as it is an isotope-labeled internal standard used for analytical quantitation. The non-labeled parent compound, Phenylacetylglutamine, is a colonic microbial metabolite that has been associated with overall mortality and cardiovascular disease in patients with CKD. It is formed by the conjugation of phenylacetate (a product of amino acid fermentation by gut microbiota) with glutamine. As a labeled standard, Phenylacetylglutamine-D5 is used to accurately measure endogenous phenylacetylglutamine levels in biological fluids by mass spectrometry.
|
|---|---|
| ln Vitro |
In vitro, stable heavy isotopes of hydrogen, carbon, and other elements have been incorporated into drug molecules, largely as tracers for quantitation during the drug development process. Phenylacetylglutamine-D5 serves this purpose as a deuterated internal standard for LC-MS/MS method development and sample analysis. Deuteration has gained attention because of its potential to affect the pharmacokinetic and metabolic profiles of drugs. However, for Phenylacetylglutamine-D5, the primary use is as an analytical standard rather than for assessing biological activity. The compound does not have direct in vitro pharmacological activity.
|
| ln Vivo |
Phenylacetylglutamine-D5 is used as a stable isotope-labeled internal standard for in vivo pharmacokinetic studies of phenylacetylglutamine. The deuterated form is added to biological samples (plasma, urine, tissue homogenates) prior to LC-MS/MS analysis to correct for matrix effects, extraction efficiency, and instrument variability. While the labeled compound itself is not administered in vivo, it is essential for the accurate quantitation of endogenous phenylacetylglutamine levels in disease states. The non-labeled Phenylacetylglutamine has been studied clinically, with elevated levels associated with increased cardiovascular risk and mortality in chronic kidney disease patients.
|
| Enzyme Assay |
For LC-MS/MS method development using Phenylacetylglutamine-D5 as internal standard, prepare calibration standards and quality control samples by spiking known amounts of unlabeled phenylacetylglutamine into blank matrix (e.g., human plasma, urine, serum). For plasma analysis, add Phenylacetylglutamine-D5 (50-100 ng/mL final concentration) to each sample (100-200 microL). Perform protein precipitation by adding 3-4 volumes of acetonitrile or methanol containing the internal standard. After vortexing and centrifugation, collect supernatant, evaporate to dryness under nitrogen, reconstitute in mobile phase (e.g., 0.1% formic acid in water:acetonitrile, 90:10), and inject onto LC-MS/MS system. Separate on C18 column (2.1 x 50 mm, 1.7 microm) with gradient elution at 0.3-0.5 mL/min. Monitor MRM transitions: m/z 265→130 for phenylacetylglutamine, m/z 270→135 for D5-labeled internal standard. Validate method for linearity, accuracy, precision, recovery, and matrix effect.
|
| Cell Assay |
For in vitro applications, use cell lysates, culture media, or hepatocyte incubations to study phenylacetylglutamine metabolism or production. For cellular uptake or metabolism studies, treat primary hepatocytes, Caco-2 cells, or kidney cells with phenylacetate (100 microM-1 mM) for 6-24 h to stimulate phenylacetylglutamine synthesis. Lysate samples are processed with Phenylacetylglutamine-D5 internal standard (10-50 ng/mL) before LC-MS/MS analysis. For permeability studies, use Caco-2 cell monolayers grown on Transwell inserts for 21 days. Add phenylacetylglutamine (1-100 microM) to apical compartment, sample basolateral compartment at various times, add internal standard, and quantify by LC-MS/MS. For plasma protein binding, incubate phenylacetylglutamine (1-50 microM) with human plasma at 37degC for 4 h, then ultrafilter, add internal standard to filtrate, and analyze.
|
| Animal Protocol |
For in vivo pharmacokinetic studies of phenylacetylglutamine, use Sprague-Dawley rats (200-300 g) or C57BL/6 mice (20-25 g). Administer phenylacetylglutamine intravenously (1-10 mg/kg) or orally (10-50 mg/kg) formulated in saline or PBS. Collect blood via tail vein at 0, 0.25, 0.5, 1, 2, 4, 6, 8, 12, 24 h post-dose into EDTA-coated tubes. Centrifuge to obtain plasma. For each sample, add Phenylacetylglutamine-D5 internal standard (50 ng/mL final), process by protein precipitation, and analyze by LC-MS/MS. Calculate PK parameters using non-compartmental analysis. For tissue distribution studies, collect brain, liver, kidney, heart, lung, and intestine at 0.5, 1, 2, 4, 8 h post-dose, homogenize, add internal standard, extract, and quantify.
|
| ADME/Pharmacokinetics |
The compound has molecular formula C13H11D₅N2O4 and molecular weight 269.31 g/mol (non-labeled: 264.28). As a deuterated internal standard, it is chemically identical to the analyte except for the five deuterium atoms. Solubility: soluble in DMSO, methanol, and water. For LC-MS/MS, stock solutions are typically prepared in methanol or acetonitrile at 1 mg/mL and stored at -20degC. Working solutions should be prepared fresh daily. The compound should be stored as a powder at -20degC, protected from light and moisture. Solutions in organic solvents can be stored at -80degC for up to 6 months.
|
| Toxicity/Toxicokinetics |
Phenylacetylglutamine-D5 is a stable isotope-labeled compound with minimal toxicity at concentrations used for analytical purposes (typically ng/mL range). Standard laboratory precautions for handling fine chemicals should be followed: use personal protective equipment (gloves, lab coat, safety glasses), avoid inhalation and ingestion. The compound is not classified as hazardous at typical research quantities. As with all deuterated standards, it is intended for research use only and not for human consumption. Consult the safety data sheet before handling. Dispose of waste in accordance with local regulations for chemical and biological waste.
|
| References | |
| Additional Infomation |
Phenylacetylglutamine is a uremic toxin and microbial metabolite derived from phenylalanine fermentation by gut bacteria. Elevated levels are associated with cardiovascular events and mortality in chronic kidney disease (CKD) patients. Phenylacetylglutamine-D5 serves as an essential internal standard for the accurate quantification of this metabolite in biological fluids by LC-MS/MS, enabling clinical research on gut microbiota-derived metabolites and their role in cardiovascular and kidney diseases. The compound has no direct therapeutic use and is not approved for clinical treatment. It is exclusively a research reagent for analytical method development and biomarker quantification.
|
| Molecular Formula |
C₁₃H₁₁D₅N₂O₄
|
|---|---|
| Molecular Weight |
269.31
|
| Exact Mass |
269.142
|
| CAS # |
1331909-01-3
|
| Related CAS # |
Phenylacetylglutamine;28047-15-6
|
| PubChem CID |
13728880
|
| Appearance |
White to off-white solid powder
|
| LogP |
2.054
|
| Hydrogen Bond Donor Count |
3
|
| Hydrogen Bond Acceptor Count |
4
|
| Rotatable Bond Count |
7
|
| Heavy Atom Count |
19
|
| Complexity |
338
|
| Defined Atom Stereocenter Count |
1
|
| SMILES |
[2H]C1=C(C(=C(C(=C1[2H])[2H])CC(=O)N[C@@H](CCC(=O)N)C(=O)O)[2H])[2H]
|
| InChi Key |
JFLIEFSWGNOPJJ-CJMNRESHSA-N
|
| InChi Code |
InChI=1S/C13H16N2O4/c14-11(16)7-6-10(13(18)19)15-12(17)8-9-4-2-1-3-5-9/h1-5,10H,6-8H2,(H2,14,16)(H,15,17)(H,18,19)/t10-/m0/s1/i1D,2D,3D,4D,5D
|
| Chemical Name |
(2S)-5-amino-5-oxo-2-[[2-(2,3,4,5,6-pentadeuteriophenyl)acetyl]amino]pentanoic acid
|
| Synonyms |
PhenylacetylglutamineD5; Phenylacetylglutamine D5
|
| 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) |
DMSO : ≥ 50 mg/mL (~185.66 mM)
|
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 1.25 mg/mL (4.64 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 12.5 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 1.25 mg/mL (4.64 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 12.5 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 1.25 mg/mL (4.64 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.7132 mL | 18.5660 mL | 37.1319 mL | |
| 5 mM | 0.7426 mL | 3.7132 mL | 7.4264 mL | |
| 10 mM | 0.3713 mL | 1.8566 mL | 3.7132 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
