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Human Endogenous Metabolite
Not fully defined. PGA2 is a prostaglandin that exerts its effects through multiple pathways. It is an endogenous inhibitor of NF-kappaB activation, blocking the nuclear translocation of the p65 subunit. It also activates heat shock factor 1 (HSF1) and induces the expression of heat shock proteins, which contribute to its cytoprotective and anti-inflammatory effects. PGA2 can also covalently modify proteins via its reactive cyclopentenone ring. |
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| ln Vitro |
PGA2 has demonstrated antiviral activity against a range of RNA and DNA viruses, including herpes simplex virus, vesicular stomatitis virus, and encephalomyocarditis virus. It also exhibits pro-apoptotic activity in cancer cells by inhibiting NF-kappaB and activating heat shock protein expression. At low micromolar concentrations (1-10 uM), PGA2 inhibits viral replication and induces apoptosis in tumor cell lines.
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| ln Vivo |
In animal models, PGA2 and its analogs (e.g., delta12-PGJ2) have shown anti-inflammatory and anti-tumor activity. However, in vivo use of PGA2 is limited due to its rapid metabolism and clearance. It can be administered intraperitoneally (i.p.) to mice at doses of 1-10 mg/kg to study its anti-inflammatory effects, but its short half-life reduces its utility as a therapeutic agent. The structurally related delta12-PGJ2 has been more extensively studied in vivo.
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| Enzyme Assay |
PGA2 is an endogenous prostaglandin. For cell-free studies, the NF-kappaB DNA-binding assay can be performed using nuclear extracts from treated cells. Alternatively, purified NF-kappaB p50/p65 proteins are incubated with PGA2 (1-100 uM) for 30 minutes at room temperature, and then incubated with a biotinylated NF-kappaB consensus oligonucleotide. The complex is detected by EMSA (electrophoretic mobility shift assay). For direct binding, surface plasmon resonance (SPR) can be used to measure the interaction between PGA2 and purified proteins (e.g., HSP90 or other potential targets). The cyclopentenone ring of PGA2 can form covalent adducts with protein thiols, which can be detected by mass spectrometry.
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| Cell Assay |
For in vitro cellular studies, human cancer cell lines (e.g., HeLa, A549, MCF-7) are seeded in 6- or 96-well plates (5×103 cells/well). Cells are treated with PGA2 (0.1-50 uM) for 24-48 hours. Cell viability is assessed by MTT or CellTiter-Glo. Apoptosis is measured by Annexin V/PI flow cytometry and caspase-3/7 activity. To study NF-kappaB inhibition, cells are pretreated with PGA2 (1-10 uM) for 2 hours and then stimulated with TNF-alpha (10 ng/mL) for 30 minutes. NF-kappaB p65 nuclear translocation is assessed by immunofluorescence, and IkappaBalpha degradation is measured by Western blot. For antiviral studies, virus-infected cells (e.g., Vero cells infected with HSV-1) are treated with PGA2 (1-10 uM), and viral titers are determined by plaque assay or by quantifying viral DNA by qPCR.
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| Animal Protocol |
For in vivo antiviral or anti-inflammatory studies, 6-8 week old female BALB/c mice are used. PGA2 (1-10 mg/kg) is administered intraperitoneally (i.p.) in a vehicle containing 10% DMSO or ethanol in PBS, either prophylactically (1-24 hours before challenge) or therapeutically (1-2 hours after challenge). For inflammatory models (e.g., LPS-induced endotoxemia), mice are injected with LPS (1 mg/kg, i.p.), and PGA2 is co-administered. Blood and tissues are collected 6-24 hours later for cytokine measurement (TNF-alpha, IL-6, IL-1beta) and NF-kappaB activity. For antiviral studies, mice are infected with a lethal dose of a virus (e.g., encephalomyocarditis virus), and survival and viral titers in target organs are measured. Due to the rapid metabolism of PGA2, repeated dosing (every 4-6 hours) may be required.
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| ADME/Pharmacokinetics |
PGA2 has a very short half-life in vivo, typically less than 1 minute in plasma due to rapid metabolism and degradation. It is rapidly taken up by cells and metabolized by 15-hydroxyprostaglandin dehydrogenase (15-PGDH) to inactive 15-keto-PGA2. It is not orally bioavailable and requires injection for in vivo studies. The rapid metabolism limits its utility as a therapeutic agent. The biologically stable analog delta12-PGJ2 is often used for in vivo studies instead.
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| Toxicity/Toxicokinetics |
PGA2 is an endogenous prostaglandin and is generally well-tolerated at low concentrations. At high concentrations (≥50 uM in vitro, >10 mg/kg in vivo), it can cause cellular toxicity and may induce apoptosis in non-target cells. It is produced endogenously during inflammation and may contribute to the resolution of inflammation. No significant genotoxicity or carcinogenicity has been reported for this endogenous compound.
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| References |
[1]. Lee SB, et al. Induction of p53-Dependent Apoptosis by Prostaglandin A2. Biomolecules. 2020 Mar 24;10(3):492.
[2]. Gorospe M, et al. Protective role of p21(Waf1/Cip1) against prostaglandin A2-mediated apoptosis of human colorectal carcinoma cells. Mol Cell Biol. 1996 Dec;16(12):6654-60. [3]. O'Brien WJ, et al. Assessment of antiviral activity, efficacy, and toxicity of prostaglandin A2 in a rabbit model of herpetic keratitis. Antimicrob Agents Chemother. 1996 Oct;40(10):2327-31. |
| Additional Infomation |
Prostaglandin A2 is a type of prostaglandin A. It functions as a metabolite in the human body. It is the conjugate acid of prostaglandin A2(1-). Prostaglandin A2 has been reported in Homo sapiens, Japanese deer, and other organisms with relevant data.
Prostaglandin A2 (PGA2) is also known as Medullin. It is derived from arachidonic acid via the cyclooxygenase (COX) pathway. PGA2 contains a cyclopentenone ring, which is reactive with thiol groups in proteins and enables the compound to exert its effects through covalent modification of target proteins. This property is distinct from other prostaglandins. The molecular formula of PGA2 is C20H30O4, and its molecular weight is 334.45. It is supplied as a solution in organic solvents and is stored at -80degC to prevent degradation. It is not approved for clinical use but is a valuable research tool for studying inflammation, apoptosis, and antiviral responses. |
| Molecular Formula |
C20H30O4
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| Molecular Weight |
334.45
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| Exact Mass |
334.214
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| CAS # |
13345-50-1
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| Related CAS # |
Prostaglandin A2-d4;201608-18-6
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| PubChem CID |
5280880
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| Appearance |
Colorless to light yellow liquid
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| Density |
1.1±0.1 g/cm3
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| Boiling Point |
515.3±50.0 °C at 760 mmHg
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| Flash Point |
279.6±26.6 °C
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| Vapour Pressure |
0.0±3.0 mmHg at 25°C
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| Index of Refraction |
1.555
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| LogP |
3.25
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
12
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| Heavy Atom Count |
24
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| Complexity |
476
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| Defined Atom Stereocenter Count |
3
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| SMILES |
CCCCC[C@@H](/C=C/C1C=CC(=O)C1C/C=C/CCCC(=O)O)O
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| InChi Key |
MYHXHCUNDDAEOZ-FOSBLDSVSA-N
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| InChi Code |
InChI=1S/C20H30O4/c1-2-3-6-9-17(21)14-12-16-13-15-19(22)18(16)10-7-4-5-8-11-20(23)24/h4,7,12-18,21H,2-3,5-6,8-11H2,1H3,(H,23,24)/b7-4-,14-12+/t16-,17-,18+/m0/s1
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| Chemical Name |
(Z)-7-[(1R,2S)-2-[(E,3S)-3-hydroxyoct-1-enyl]-5-oxocyclopent-3-en-1-yl]hept-5-enoic acid
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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 Note: (1). This product requires protection from light (avoid light exposure) during transportation and storage. (2). Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture. |
| 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 | 2.9900 mL | 14.9499 mL | 29.8998 mL | |
| 5 mM | 0.5980 mL | 2.9900 mL | 5.9800 mL | |
| 10 mM | 0.2990 mL | 1.4950 mL | 2.9900 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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