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6-keto Prostaglandin F1α

Cat No.:V82229 Purity: ≥98%
6-keto Prostaglandin F1α is an endogenously produced metabolite present in cerebrospinal fluid, urine and blood and may be utilized to study meningitis, rheumatoid arthritis and cardiopulmonary resuscitation.
6-keto Prostaglandin F1α
6-keto Prostaglandin F1α Chemical Structure CAS No.: 58962-34-8
Product category: IκB IKK
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
1mg
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Product Description
6-keto Prostaglandin F1α is an endogenously produced metabolite present in cerebrospinal fluid, urine and blood and may be utilized to study meningitis, rheumatoid arthritis and cardiopulmonary resuscitation.
6-keto Prostaglandin F1alpha (CAS#: 58962-34-8) is a physiologically inactive, non-enzymatic hydrolysis product of prostacyclin (PGI2), a potent vasodilator and inhibitor of platelet aggregation. It serves as a stable metabolite marker for in vivo prostacyclin biosynthesis and is found in mammalian tissues, urine, and cerebrospinal fluid.
Biological Activity I Assay Protocols (From Reference)
Targets
Human Endogenous Metabolite
No direct pharmacological receptor target; 6-keto PGF1alpha is the stable inactive hydrolysis product of prostacyclin (PGI2). Its levels are measured as an indirect marker of PGI2 production rather than a direct ligand binding to prostaglandin receptors, though PGI2 itself targets the prostacyclin receptor (IP) to exert vasodilatory and anti-aggregatory effects.
ln Vitro
Endogenous metabolites are those that the Kyoto Encyclopedia of Genes and Genomes has identified as products or substrates of the approximately 1900 metabolic enzymes that are encoded in human genome. Numerous of these metabolites have been shown to have harmful effects, as evidenced by the body of literature [1].
As a stable hydrolysis product of prostacyclin (PGI2), 6-keto PGF1alpha is used as a quantitative biomarker of PGI2 biosynthesis in vitro and in vivo. Elevated levels of 6-keto PGF1alpha are observed in response to bleeding, trauma, endotoxins, and certain disease states such as epidemic hemorrhagic fever, obstructive suppurative cholangitis, and gynecological carcinomas. Conversely, decreased plasma levels are found in patients with arteriosclerosis, diabetes, and hyperlipidemia, reflecting reduced PGI2 production.
ln Vivo
In animal models of circulatory shock (bleeding, injury, endotoxins), plasma levels of 6-keto PGF1alpha increase as a reflection of enhanced PGI2 synthesis. The compound itself has no direct biological activity in vivo, but its levels correlate with PGI2 activity. Changes in the TXA2/PGI2 ratio, reflected by 6-keto PGF1alpha measurement, can indicate platelet aggregation, thrombus formation, and progression of arteriosclerosis and coronary heart disease.
Enzyme Assay
No specific enzyme/receptor binding assay for 6-keto PGF1alpha, as it is an inactive metabolite. Quantification in biological samples (plasma, urine, cell culture media) is performed via enzyme-linked immunosorbent assay (ELISA) using specific antibodies or by liquid chromatography-mass spectrometry (LC-MS). (1) For ELISA: coat plates with anti-6-keto PGF1alpha antibody, add samples and HRP-conjugated tracer, incubate at 4degC overnight, wash, add substrate, measure OD450. (2) For LC-MS: extract samples with solid-phase extraction, separate on a C18 reverse-phase column, and detect using multiple reaction monitoring (MRM).
Cell Assay
No direct cellular activity. However, (1) Seed endothelial cells or vascular smooth muscle cells in culture, stimulate with cytokines (IL-1beta, TNF-alpha) or shear stress to induce PGI2 production, collect culture supernatant. (2) Measure 6-keto PGF1alpha levels in supernatant by ELISA or LC-MS as a readout of PGI2 synthase activity. (3) Quantify 6-keto PGF1alpha concentration in pg/mL or nM using a standard curve, normalize to cell number or protein concentration. (4) Compare stimulated vs. control groups to assess endothelial PGI2 production capacity.
Animal Protocol
(1) Use 6-8 week old male Sprague-Dawley rats or C57BL/6 mice (200-300 g or 20-25 g). (2) Administer compounds or perform interventions (e.g., LPS injection, ischemia-reperfusion, vascular injury). (3) Collect blood from tail vein or cardiac puncture into tubes containing indomethacin (10 uM) and EDTA, centrifuge at 4degC to obtain plasma. (4) Also collect urine via metabolic cages over 24 h. (5) Measure 6-keto PGF1alpha in plasma or urine by ELISA or LC-MS/MS. (6) Normalize urine levels to creatinine concentration. (7) Compare levels between treated and control groups to assess PGI2 biosynthesis.
ADME/Pharmacokinetics
6-keto PGF1alpha is not administered as a drug but is measured as a biomarker. The half-life of prostaglandins in circulation is very short (1-5 minutes), and 6-keto PGF1alpha is the stable end product. Standard formulation for prostaglandin measurement: blood samples are collected into chilled tubes containing 10 uM indomethacin and 5 mM EDTA to prevent ex vivo prostaglandin synthesis and degradation. Plasma is separated by centrifugation at 2000 × g for 15 min at 4degC and stored at -80degC until analysis. 6-keto PGF1alpha is stable in plasma at -80degC for months.
Toxicity/Toxicokinetics
No direct toxicity. As an endogenous metabolite, 6-keto PGF1alpha itself is non-toxic. In vitro cytotoxicity assays (e.g., CCK-8 on HEK293 cells) with synthetic 6-keto PGF1alpha show no cytotoxicity at concentrations up to 100 uM. In vivo, administration of 6-keto PGF1alpha (mg/kg range) in animal models does not cause overt toxicity. The compound is intended for research use only, not for human therapeutic use.
References

[1]. Endogenous toxic metabolites and implications in cancer therapy. Oncogene. 2020 Aug;39(35):5709-5720.

[2]. Eicosanoids in human ventricular cerebrospinal fluid following severe brain injury. Prostaglandins. 1987 Dec;34(6):877-87.

[3]. Plasma levels and urinary excretion of prostaglandins in patients with rheumatoid arthritis. Clin Rheumatol. 1983 Dec;2(4):401-6.

[4]. Concentrations of prolactin and prostaglandins during and after cardiopulmonary resuscitation. Crit Care Med. 1995 Aug;23(8):1347-55.

Additional Infomation
6-O-Prostaglandin F1α is a form of prostaglandin F1α with a ketone substituent at the 6-position. It is a metabolite in both humans and mice. Its function is related to prostaglandin F1α. It is the conjugate acid of 6-O-Prostaglandin F1α(1-). 6-Ketoprostaglandin F1α has been reported to be detected in Homo sapiens, with relevant data available. 6-Ketoprostaglandin F1α is a form of prostaglandin F1α with a ketone group modified at the 6-position. 6-Ketoprostaglandin F1α (6-ketoPGF1α) is a metabolite of prostaglandin I2 (PGI2) and is inactive. The concentration of 6-ketoPGF1α in a sample may be related to the level of PGI2 synthesis. 6-Ketoprostaglandin F1α levels are elevated in certain types of cancer. It is a physiologically active and stable hydrolysis product of prostaglandin and is present in almost all mammalian tissues.
6-keto Prostaglandin F1alpha is a stable, inactive hydrolysis product of prostacyclin (PGI2) and is widely used as a quantitative marker for PGI2 biosynthesis in cardiovascular research, thrombosis studies, and inflammation models. PGI2 has a very short half-life (1-5 min in blood), so direct measurement is impractical; hence, 6-keto PGF1alpha serves as the standard readout. Elevated levels are seen in conditions with increased PGI2 production, while decreased levels indicate endothelial dysfunction. This compound is not FDA-approved and is strictly for research use as a biomarker and internal standard in LC-MS assays.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C20H34O6
Molecular Weight
370.48
Exact Mass
370.235
CAS #
58962-34-8
PubChem CID
5280888
Appearance
White to off-white solid powder
Density
1.2±0.1 g/cm3
Boiling Point
575.3±50.0 °C at 760 mmHg
Flash Point
315.8±26.6 °C
Vapour Pressure
0.0±3.6 mmHg at 25°C
Index of Refraction
1.561
LogP
0.93
Hydrogen Bond Donor Count
4
Hydrogen Bond Acceptor Count
6
Rotatable Bond Count
13
Heavy Atom Count
26
Complexity
461
Defined Atom Stereocenter Count
5
SMILES
CCCCC[C@@H](/C=C/[C@H]1[C@@H](C[C@@H]([C@@H]1CC(=O)CCCCC(=O)O)O)O)O
InChi Key
KFGOFTHODYBSGM-ZUNNJUQCSA-N
InChi Code
InChI=1S/C20H34O6/c1-2-3-4-7-14(21)10-11-16-17(19(24)13-18(16)23)12-15(22)8-5-6-9-20(25)26/h10-11,14,16-19,21,23-24H,2-9,12-13H2,1H3,(H,25,26)/b11-10+/t14-,16+,17+,18+,19-/m0/s1
Chemical Name
7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]cyclopentyl]-6-oxoheptanoic 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)
Solubility Data
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
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
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*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 : PEG300Tween 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).
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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)]
*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.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL 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).
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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders


Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.6992 mL 13.4960 mL 26.9920 mL
5 mM 0.5398 mL 2.6992 mL 5.3984 mL
10 mM 0.2699 mL 1.3496 mL 2.6992 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.

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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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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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