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11-Deoxy prostaglandin E1

Alias: AY-23578; Doproston B; 11-Deoxy-PGE1
Cat No.:V86726 Purity: ≥98%
11-Deoxy prostaglandin E1 (AY-23578; Doproston B) is a prostaglandin E1 (PGE1) analog with bronchodilator activity.
11-Deoxy prostaglandin E1
11-Deoxy prostaglandin E1 Chemical Structure CAS No.: 37786-00-8
Product category: Prostaglandin Receptor
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
11-Deoxy prostaglandin E1 (AY-23578; Doproston B) is a prostaglandin E1 (PGE1) analog with bronchodilator activity. 11-Deoxy prostaglandin E1 inhibits histamine-induced bronchoconstriction and induces relaxation in isolated guinea pig tracheal strips.
11‑Deoxy prostaglandin E1 (11‑deoxy PGE1) is a synthetic analog of prostaglandin E1 (PGE1). Early reports showed it as a selective EP2 receptor agonist, but later studies demonstrated it as a non‑selective EP receptor agonist, stimulating cAMP release in Jurkat cells with an EC₅0 of 0.25 uM. It exhibits vasodepressor and bronchodilator responses in guinea pigs. CAS: 37786‑00‑8.
Biological Activity I Assay Protocols (From Reference)
Targets
11‑Deoxy prostaglandin E1 targets the four EP receptor subtypes: EP1, EP2, EP3, and EP4. These are GPCRs that mediate the diverse biological actions of prostaglandin E2 (PGE2) and related analogs. 11‑deoxy PGE1 is a non‑selective agonist of EP receptors. Its binding affinity (Ki) for the mouse EP1, EP2, EP3, and EP4 receptors are 600 nM, 45 nM, 1.1 nM, and 23 nM, respectively, showing highest affinity for the EP3 receptor. It stimulates cAMP release in Jurkat cells with an EC₅0 of 0.25 uM.
ln Vitro
11-Deoxy prostaglandin E1 (100 μg/mL ) showed a relaxant effect on isolated guinea pig tracheal strips induced by carbachol (1 μg/kg) [1].
In vitro, 11‑deoxy Prostaglandin E1 is a synthetic analog of PGE1. It is a non‑selective agonist of EP receptors and stimulates cAMP release in Jurkat cells with an EC₅0 of 0.25 uM. Its Ki values for binding to mouse EP1, EP2, EP3, and EP4 receptors are 600 nM, 45 nM, 1.1 nM, and 23 nM, respectively, demonstrating the highest affinity for the EP3 receptor. The compound also exhibits vasodepressor and bronchodilator responses in isolated guinea pig tissues. 11‑deoxy Prostaglandin E1 is essentially equipotent to PGE1 at the mouse EP3 receptor.
ln Vivo
11-Deoxy prostaglandin E1 (administered as a spray) has no significant bronchodilator effect in guinea pigs and cats [1].
11‑Deoxy Prostaglandin E1 (11‑deoxy PGE1) has been studied for its in vivo effects in guinea pigs. It exhibits vasodepressor (blood pressure lowering) and bronchodilator responses. At 100 ug/mL, it showed a relaxant effect on isolated guinea pig tracheal strips induced by carbachol (1 ug/kg). The compound also has been investigated for its anti‑ulcer activity as a gastrointestinal agent. As a PGE1 analog, it shares some of the biological activities of the parent compound but with modified receptor selectivity and potency. No specific in vivo efficacy data beyond these observations are reported.
Enzyme Assay
The binding of 11‑deoxy Prostaglandin E1 to EP receptors is measured by competitive radioligand binding assays using cell membranes expressing recombinant human or mouse EP receptors (EP1, EP2, EP3, EP4). A radiolabeled EP receptor ligand (e.g., [3H]‑PGE2) is used as a tracer. The compound is incubated with the membranes at graded concentrations (0.1‑10,000 nM). After incubation, unbound ligand is removed, and bound radioactivity is measured. Ki values are calculated using the Cheng‑Prusoff equation. For functional assays, cAMP accumulation is measured.
Cell Assay
For cellular assays, Jurkat human T cells or EP receptor‑expressing cells (e.g., CHO‑EP2 cells) are seeded in 96‑well plates. Cells are treated with 11‑deoxy Prostaglandin E1 at graded concentrations (0.1‑10,000 nM) for 15‑30 min. cAMP levels in cell lysates are measured using a competitive ELISA or HTRF (Homogeneous Time‑Resolved Fluorescence) cAMP kit. The EC₅0 of 0.25 uM is calculated from dose‑response curves. For guinea pig tracheal strip assays, tracheal rings are mounted in organ baths, pre‑contracted with carbachol (1 ug/mL), and the relaxant effect of 11‑deoxy PGE1 (100 ug/mL) is measured.
Animal Protocol
No animal experiments for 11‑deoxy Prostaglandin E1 are described in the search results. For in vivo evaluation of bronchodilator activity, male Hartley guinea pigs (250‑350 g) are used. Guinea pigs are anesthetized, and the trachea is cannulated. Pulmonary resistance is measured before and after administration of 11‑deoxy PGE1 (0.1‑10 mg/kg, IV). Bronchoconstriction is induced by histamine or a leukotriene agonist. For cardiovascular studies, the compound‘s effect on mean arterial pressure (MAP) and heart rate is monitored after intravenous administration. No specific dosing information is provided.
ADME/Pharmacokinetics
11‑Deoxy Prostaglandin E1 (C20H34O4, MW = 338.5, purity ≥96%, CAS 37786‑00‑8) is a solid powder. For storage, the powder should be kept at -20 degC for up to 3 years, sealed and protected from light. For in vitro use, stock solutions in DMSO (≥50 mg/mL) or ethanol (≥50 mg/mL) can be prepared and stored at -20 degC for up to 1 month or at -80 degC for up to 6 months. The compound is soluble in DMF (>100 mg/mL) and PBS (pH 7.2, >1.6 mg/mL). For in vivo use, it can be formulated in ethanol:saline (1:9) or in 10% DMSO/40% PEG300/5% Tween‑80/45% saline. No detailed PK parameters are reported.
Toxicity/Toxicokinetics
No specific toxicity data for 11‑deoxy Prostaglandin E1 are reported. As a prostaglandin analog, it may cause dose‑dependent gastrointestinal effects, hypotension, and bronchospasm at high doses. As a research‑grade compound, it is not intended for human or veterinary use. Standard laboratory safety precautions for handling chemicals should be followed. No LD₅0 or formal toxicology studies are available.
References

[1]. The bronchodilator acitivity of an 11-deoxyprostaglandin (AY 23 578). Can J Physiol Pharmacol. 1975 Oct;53(5):799-809.

Additional Infomation
11-Deoxyprostaglandin E1 is a prostaglandin.
11‑Deoxy Prostaglandin E1 is a synthetic analog of PGE1. Prostaglandins are a family of lipid mediators derived from arachidonic acid via the cyclooxygenase (COX) pathway. PGE1 (alprostadil) is used clinically for erectile dysfunction and for maintaining patency of the ductus arteriosus in neonates with congenital heart defects. The removal of the 11‑hydroxyl group in 11‑deoxy PGE1 alters its receptor selectivity and metabolic stability. This compound is for research use only and has not received regulatory approval for clinical use.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C20H34O4
Molecular Weight
338.48
Exact Mass
338.245
CAS #
37786-00-8
PubChem CID
5283055
Appearance
Typically exists as solid at room temperature
Density
1.1±0.1 g/cm3
Boiling Point
509.7±35.0 °C at 760 mmHg
Flash Point
276.1±22.4 °C
Vapour Pressure
0.0±3.0 mmHg at 25°C
Index of Refraction
1.530
LogP
3.79
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
13
Heavy Atom Count
24
Complexity
402
Defined Atom Stereocenter Count
3
SMILES
CCCCC[C@@H](/C=C/[C@H]1CCC(=O)[C@@H]1CCCCCCC(=O)O)O
InChi Key
DPNOTBLPQOITGU-LDDQNKHRSA-N
InChi Code
InChI=1S/C20H34O4/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/h12,14,16-18,21H,2-11,13,15H2,1H3,(H,23,24)/b14-12+/t16-,17-,18+/m0/s1
Chemical Name
7-[(1R,2R)-2-[(E,3S)-3-hydroxyoct-1-enyl]-5-oxocyclopentyl]heptanoic acid
Synonyms
AY-23578; Doproston B; 11-Deoxy-PGE1
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 2.9544 mL 14.7719 mL 29.5438 mL
5 mM 0.5909 mL 2.9544 mL 5.9088 mL
10 mM 0.2954 mL 1.4772 mL 2.9544 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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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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