Physicochemical Properties
| Molecular Formula | C10H11NO3 |
| Molecular Weight | 193.20 |
| Exact Mass | 193.073 |
| CAS # | 500-98-1 |
| Related CAS # | N-(Phenylacetyl-d5)glycine;1189920-31-7 |
| PubChem CID | 68144 |
| Appearance | White to off-white solid |
| Density | 1.2±0.1 g/cm3 |
| Boiling Point | 476.5±38.0 °C at 760 mmHg |
| Melting Point | 144ºC |
| Flash Point | 242.0±26.8 °C |
| Vapour Pressure | 0.0±1.3 mmHg at 25°C |
| Index of Refraction | 1.558 |
| LogP | 0.18 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 4 |
| Heavy Atom Count | 14 |
| Complexity | 209 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | O=C(C([H])([H])C1C([H])=C([H])C([H])=C([H])C=1[H])N([H])C([H])([H])C(=O)O[H] |
| InChi Key | UTYVDVLMYQPLQB-UHFFFAOYSA-N |
| InChi Code | InChI=1S/C10H11NO3/c12-9(11-7-10(13)14)6-8-4-2-1-3-5-8/h1-5H,6-7H2,(H,11,12)(H,13,14) |
| Chemical Name | 2-(2-phenylacetamido)acetic acid |
| 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) |
Biological Activity
| Targets | β2 adrenoceptor Microbial Metabolite Human Endogenous Metabolite. Myocardial ischemia/reperfusion (I/R) injury is closely related to cardiomyocyte apoptosis. Stimulating β2 adrenergic receptor (β2AR) can effectively combat cardiomyocyte apoptosis. Previous studies demonstrate that the gut microbial metabolite phenylacetylglycine (PAGly) can stimulate β2AR. However, the effect of PAGly on myocardial I/R injury remains unknown. |
| ln Vitro | In neonatal mouse cardiomyocytes (NMCM), phenylacetylglycine (10-100 μM; 30 minutes prior to H/R injury) decreases deoxygenated (H/R) injury-induced apoptosis and activates Gαi and Gαs signaling [1]. |
| ln Vivo | PAGly significantly suppressed H/R injury-induced apoptosis in NMCMs and inhibited apoptosis in myocardial I/R injured mice in vivo. We verified that PAGly activated the anti-apoptotic Gαi/PI3K/AKT signaling cascade in NMCMs via stimulating β2AR signaling. Continuous administration of PAGly at an appropriate dose could inhibit apoptosis and reduce the infarct size resulting from I/R injury in mice. However, high-dose PAGly treatment was associated with a higher mortality rate. Moreover, we demonstrated that Aspirin reduced the infarct size and the high mortality caused by high doses of PAGly in I/R injured mice [1]. |
| Enzyme Assay | The hypoxia/reoxygenation (H/R) model was established using the neonatal mouse cardiomyocytes (NMCMs). Different doses of PAGly were used to treat NMCMs, and apoptosis was detected by terminal deoxynucleotidyl transferase-mediated nick end labeling (TUNEL) staining. Additionally, the level of cyclic adenosine monophosphate (cAMP) was examined by using a cAMP detection kit [1]. |
| Cell Assay |
Apoptosis Analysis[1] Cell Types: Neonatal mouse cardiomyocytes (NMCMs) Tested Concentrations: 10, 33 and 100 μM Incubation Duration: Half an hour before H/R injury Experimental Results: Inhibited disreoxygenation injury apoptosis. Western Blot Analysis[1] Cell Types: Neonatal induced mouse cardiomyocytes (NMCMs) Tested Concentrations: 10, 33 and 100 μM Incubation Duration: Half an hour before H/R injury Experimental Results: Dramatically diminished the ratio of Bax/Bcl2 and cleaved-caspase 3 expression. Enhanced p-PI3K protein expression. cAMP levels were increased in the early stage and then gradually diminished. |
| Animal Protocol | Mouse model of myocardial I/R injury was established in C57BL/6 mice, and different doses of phenylacetic acid were administrated intraperitoneally. Apoptosis of myocardial cells was detected by TUNEL and α-actin staining. The area at risk and the infarct areas were identified by 2,3,5-triphenyltetrazolium chloride (TTC) and Evans blue staining. Western blotting was used to measure the protein expression levels of phosphorylated phosphatidylinositol 3-kinase (p-PI3K), total Akt (t-Akt), phosphorylated Akt (p-AKT), Bcl-2-associated X protein (Bax), B-cell lymphoma-2 (Bcl-2), cleaved caspase-3 [1]. |
| References |
[1]. The gut microbial metabolite phenylacetylglycine protects against cardiac injury caused by ischemia/reperfusion through activating β2AR. Arch Biochem Biophys. 2021 Jan 15;697:108720. |
| Additional Infomation |
Phenylacetylglycine is a N-acylglycine that is glycine substituted on nitrogen with a phenylacetyl group. It has a role as a mouse metabolite and a human metabolite. It is a monocarboxylic acid amide, a monocarboxylic acid and a N-acylglycine. It is a conjugate acid of a phenylacetylglycine(1-). Phenylacetylglycine has been reported in Homo sapiens, Trypanosoma brucei, and other organisms with data available. N-Phenylacetylglycine is a metabolite found in or produced by Saccharomyces cerevisiae. |
Solubility Data
| Solubility (In Vitro) | DMSO : 100 mg/mL (517.60 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 0.83 mg/mL (4.30 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 8.3 mg/mL clear DMSO stock solution to 400 μL of PEG300 and mix evenly; then add 50 μL of Tween-80 to the above solution and mix evenly; then add 450 μL of 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: ≥ 0.83 mg/mL (4.30 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 8.3 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. Solubility in Formulation 3: ≥ 0.83 mg/mL (4.30 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (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 8.3 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 5.1760 mL | 25.8799 mL | 51.7598 mL | |
| 5 mM | 1.0352 mL | 5.1760 mL | 10.3520 mL | |
| 10 mM | 0.5176 mL | 2.5880 mL | 5.1760 mL |