| Size | Price | Stock | Qty |
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| 1mg |
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| 5mg |
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| Other Sizes |
| Targets |
13,14‑Dihydro‑15‑keto‑prostaglandin A2 targets prostaglandin receptors, primarily the EP and DP receptor subtypes, with reduced affinity compared to its precursor PGA2. The compound also modulates intracellular signaling pathways through interaction with peroxisome proliferator‑activated receptors (PPARs), particularly PPARgamma, and may induce cell cycle arrest and apoptosis in cancer cells. Its primary role is as a metabolite marker rather than a potent receptor agonist.
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| ln Vitro |
In vitro, 13,14‑dihydro‑15‑keto‑prostaglandin A2 exhibits antiproliferative activity against various cancer cell lines, including human leukemia HL‑60 cells and breast cancer MCF‑7 cells, with IC₅0 values typically in the micromolar range. The compound induces apoptosis through activation of caspase‑3 and upregulation of pro‑apoptotic proteins such as Bax, while downregulating anti‑apoptotic proteins such as Bcl‑2. It also inhibits the nuclear factor kappa‑B (NF‑kappaB) pathway, reducing the production of pro‑inflammatory cytokines in activated macrophages.
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| ln Vivo |
No in vivo studies have been specifically reported for 13,14‑dihydro‑15‑keto‑prostaglandin A2 itself; however, it is a metabolite of PGA2 formed in the liver and plasma. In animal models of inflammation, PGA2 and its metabolites (including the 13,14‑dihydro‑15‑keto derivative) exhibit anti‑inflammatory activity when administered intraperitoneally at doses of 0.1-10 mg/kg in mice. The compound is rapidly cleared from circulation with a half‑life of less than 5 minutes in plasma due to rapid oxidation and reduction by prostaglandin dehydrogenases.
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| Enzyme Assay |
The prostaglandin receptor binding affinity of this compound can be assessed using a radioligand competition binding assay. Cell membranes expressing a specific prostaglandin receptor subtype (e.g., EP2) are incubated with [3H]‑PGE2 (for EP receptors) at its Kd concentration in the presence of increasing concentrations of 13,14‑dihydro‑15‑keto‑PGA2 (0.01-100 uM) for 60 minutes at 25degC. Non‑specific binding is determined using 10 uM unlabeled PGE2. Bound radioactivity is measured by filtration through glass fiber filters and scintillation counting to calculate the inhibitory concentration (IC₅0) and equilibrium dissociation constant (Ki).
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| Cell Assay |
Cell viability can be assessed using the MTT assay. Cancer cells (e.g., HL‑60 or MCF‑7) are seeded in 96‑well plates at a density of 5×103-1×10⁴ cells per well and treated with 13,14‑dihydro‑15‑keto‑prostaglandin A2 at concentrations ranging from 0.1-100 uM for 24-72 hours. After treatment, MTT reagent (0.5 mg/mL) is added and incubated for 4 hours at 37degC, followed by solubilization with DMSO (100 uL/well). Absorbance is measured at 570 nm using a microplate reader. The half‑maximal inhibitory concentration (IC₅0) is calculated from the dose‑response curve.
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| Animal Protocol |
Apoptosis can be assessed by flow cytometry using annexin V‑FITC/propidium iodide double staining. Cells treated with the compound for 24-48 hours are harvested, washed with cold PBS, and resuspended in binding buffer. Annexin V‑FITC (5 uL) and propidium iodide (5 uL) are added, and the mixture is incubated for 15 minutes at room temperature in the dark. Stained cells are analyzed by flow cytometry within 1 hour. Early apoptotic cells (annexin V+/PI-) and late apoptotic cells (annexin V+/PI+) are quantified.
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| ADME/Pharmacokinetics |
Caspase‑3 activation can be assessed using a colorimetric assay kit. Treated cells are lysed in ice‑cold lysis buffer (50 mM HEPES, pH 7.4, 5 mM CHAPS, 5 mM DTT). Cell lysates are cleared by centrifugation at 10,000×g for 10 minutes. The supernatant is incubated with the caspase‑3 substrate Ac‑DEVD‑pNA (200 uM) at 37degC for 2 hours. The release of p‑nitroaniline is measured at 405 nm using a microplate reader. Caspase‑3 activity is expressed as fold‑change relative to untreated controls.
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| Toxicity/Toxicokinetics |
No specific pharmacokinetic data are available for 13,14‑dihydro‑15‑keto‑prostaglandin A2. As a prostaglandin metabolite, it is rapidly formed from PGA2 by the action of 15‑hydroxyprostaglandin dehydrogenase (15‑PGDH) and ∆13‑14 reductase. The compound is further metabolized by beta‑oxidation and omega‑oxidation pathways and is eliminated primarily in the urine. The half‑life of prostaglandin metabolites in human plasma is typically less than 5-10 minutes due to rapid clearance by the liver and lungs.
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| References | |
| Additional Infomation |
15-Keto-13,14-Dihydroprostaglandin A2 is a prostaglandin.
No toxicity data (LD₅0) are available for 13,14‑dihydro‑15‑keto‑prostaglandin A2 in the literature. Prostaglandin metabolites are generally considered to have low acute toxicity, as they are endogenous compounds that are rapidly cleared. However, higher doses may cause gastrointestinal disturbances, hypotension, and uterine contractions due to residual prostaglandin‑like activity. The compound should be handled as a potentially hazardous chemical with appropriate personal protective equipment (lab coat, gloves, safety goggles). |
| Molecular Formula |
C20H30O4
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|---|---|
| Molecular Weight |
334.45
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| Exact Mass |
334.214
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| CAS # |
74872-89-2
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| PubChem CID |
5283042
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| Appearance |
Typically exists as solid at room temperature
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| Density |
1.0±0.1 g/cm3
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| Boiling Point |
510.5±33.0 °C at 760 mmHg
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| Flash Point |
276.6±21.9 °C
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| Vapour Pressure |
0.0±2.8 mmHg at 25°C
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| Index of Refraction |
1.499
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| LogP |
3.1
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
13
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| Heavy Atom Count |
24
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| Complexity |
476
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| Defined Atom Stereocenter Count |
2
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| SMILES |
CCCCCC(=O)CC[C@H]1C=CC(=O)[C@@H]1C/C=C\CCCC(=O)O
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| InChi Key |
FMKLAIBZMCURLI-BFVRRIQPSA-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/h4,7,13,15-16,18H,2-3,5-6,8-12,14H2,1H3,(H,23,24)/b7-4-/t16-,18+/m0/s1
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| Chemical Name |
(Z)-7-[(1R,5S)-2-oxo-5-(3-oxooctyl)cyclopent-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 |
| 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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