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Prostaglandin D2

Cat No.:V40583 Purity: ≥98%
Prostaglandin D2 (PGD2) is one of the major prostaglandins actively generated in the brains of a variety of mammals.
Prostaglandin D2
Prostaglandin D2 Chemical Structure CAS No.: 41598-07-6
Product category: New2
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
1mg
Other Sizes

Other Forms of Prostaglandin D2:

  • Prostaglandin D2-d9 (PGD2-d9)
  • Prostaglandin D2-d4 (PGD2-d4)
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Top Publications Citing lnvivochem Products
Product Description
Prostaglandin D2 (PGD2) is one of the major prostaglandins actively generated in the brains of a variety of mammals. Prostaglandin D2 is one of the most potent endogenous sleep promoters. Prostaglandin D2 plays a protective role by suppressing inflammation.
Prostaglandin D2 (CAS#: 41598-07-6) is a major prostaglandin actively produced in the brain of various mammals. It is one of the most potent endogenous sleep-promoting substances. PGD2 plays a protective role by suppressing inflammation. It is the principal cyclooxygenase metabolite of arachidonic acid, released upon activation of mast cells and synthesized by alveolar macrophages. Its molecular formula is C20H32O5 with a molecular weight of 352.47 g/mol.
Biological Activity I Assay Protocols (From Reference)
Targets
Prostaglandin D2 targets multiple receptors including DP1 (PTGDR) and DP2 (CRTH2) receptors. It binds to these G protein-coupled receptors to exert its biological effects. Through DP1 receptor activation, PGD2 induces vasodilation and inhibits platelet aggregation. Through DP2 receptor activation, it promotes chemotaxis of eosinophils, basophils, and Th2 cells. PGD2 plays important roles in sleep regulation, inflammation, and allergic responses.
ln Vitro
In vitro, prostaglandin D2 is a bioactive lipid that plays a significant role in various physiological processes including inflammation, allergic responses, and the regulation of sleep-wake cycles. Its activity is typically evaluated using receptor binding assays and functional assays measuring cAMP accumulation or calcium flux in cells expressing DP1 or DP2 receptors. Its effects on immune cell chemotaxis and cytokine production are also assessed. However, specific potency data are not detailed in the available literature.
ln Vivo
In A2AR KO mice, prostaglandin D2 (PGD2; injected into the lateral ventricle; 5-50 pmol/min; for 6 hours between 20:00 and 2:00) promotes sleep-wake curves [2].
In vivo, prostaglandin D2 is one of the most potent endogenous sleep-promoting substances. It plays a protective role by suppressing inflammation. It is released upon activation of mast cells and is synthesized by alveolar macrophages. PGD2 is involved in the regulation of sleep-wake cycles, allergic responses, and inflammation. Its levels are elevated in various inflammatory conditions. As a natural hormone, it is not administered as a therapeutic agent.
Enzyme Assay
Cell-free assays for prostaglandin D2 involve evaluating its binding affinity to DP1 and DP2 receptors. Radioligand binding assays are performed using membrane preparations from cells expressing recombinant receptors. PGD2 is incubated with membranes and a radiolabeled ligand. Competition binding experiments determine Ki values. Its chemical purity and identity are confirmed by HPLC, NMR, and mass spectrometry. The compound is typically dissolved in ethanol or DMSO for assay preparation.
Cell Assay
In vitro cellular assays for prostaglandin D2 typically involve treating cells expressing DP1 or DP2 receptors with various concentrations of PGD2. Functional assays such as cAMP accumulation (for DP1) or calcium flux (for DP2) are used to measure receptor activation. Immune cell chemotaxis assays are performed to assess DP2-mediated effects. Cytokine production is measured by ELISA. The compound's effects on cell signaling and function are assessed.
Animal Protocol
Animal/Disease Models: Male WT and A2AR KO mice of inbred C57BL/6 strain (body weight 23-27 g, 11-13 weeks old) [1]
Doses: 5, 10, 20 or 50 pmol/min
Route of Administration: Inject into lateral ventricle; last 6 hrs (hrs (hours)) between 20:00 and 2:00.
Experimental Results: Induced sleep-wake curve.
In vivo animal studies for prostaglandin D2 are conducted in models of sleep, inflammation, and allergy. The compound is administered via various routes including intracerebroventricular (for sleep studies) or systemic administration. Sleep-wake patterns are monitored using EEG/EMG recordings. Inflammatory markers are measured in serum and tissues. However, specific dosing regimens and experimental protocols are not extensively documented in the available literature. Prostaglandin D2 is a research tool for studying sleep and inflammation.
ADME/Pharmacokinetics
Pharmacokinetic properties of prostaglandin D2 include a molecular weight of 352.47 g/mol and molecular formula C20H32O5. As a prostaglandin, it has a short half-life in circulation due to rapid metabolism. The compound is typically stored at appropriate conditions as a research reagent. Detailed ADME parameters such as half-life, Cmax, and AUC are not extensively reported in the available literature. It is typically handled as a solution in organic solvents and stored at low temperatures.
Toxicity/Toxicokinetics
The toxicity profile of prostaglandin D2 is related to its physiological role as a hormone. It is generally well-tolerated at physiological concentrations. At supraphysiological levels, it may cause inflammatory and allergic responses. The compound is intended for research use only and not for therapeutic applications. Standard safety precautions should be followed when handling this compound.
References

[1]. Transport of prostaglandin D2 into brain. Brain Res. 1986 Oct 22;385(2):321-8.

[2]. Adenosine A2A receptor deficiency attenuates the somnogenic effect of prostaglandin D2 in mice. Acta Pharmacol Sin. 2017 Apr;38(4):469-476.

[3]. Prostaglandin D2 Attenuates NSC 125066-Induced Lung Inflammation and Pulmonary Fibrosis. PLoS One. 2016 Dec 19;11(12):e0167729.

Additional Infomation
Prostaglandin D2 is a type of prostaglandin D compound with the structure prostaglandin-5,13-diene-1-acid, substituted with hydroxyl groups at positions 9 and 15 and a carbonyl group at position 11 (5Z,9α,13E,15S- stereoisomer). It is a metabolite in both humans and mice. It is the conjugate acid of prostaglandin D2(1-). It is a major metabolite of arachidonic acid cyclooxygenase. Prostaglandin D2 is released upon activation of mast cells, and it can also be synthesized by alveolar macrophages. Prostaglandin D2 has various biological functions, the most important of which are bronchoconstriction, inhibition of platelet-activating factor, and cytotoxicity. Prostaglandin D2 has been reported to be detected in Homo sapiens, Gersemia fruticosa, and Larix sibirica, and relevant data are available for reference. Prostaglandin D2 is an eicosate compound produced by the action of prostaglandin H2 on prostaglandin D2 synthase. Prostaglandin D2 mediates vasodilation, smooth muscle contraction, and circadian rhythms. This prostaglandin may also be associated with male pattern baldness. Arachidonic acid is the main product of arachidonic acid metabolism by cyclooxygenase. It is released upon mast cell activation and can also be synthesized by alveolar macrophages. Among its many biological functions, the most important are its bronchoconstriction, platelet-activating factor inhibition, and cytotoxic effects.
Prostaglandin D2 is a major prostaglandin produced in the brain that acts as a potent endogenous sleep-promoting substance and suppresses inflammation. It is the principal cyclooxygenase metabolite of arachidonic acid. Its molecular formula is C20H32O5 with a molecular weight of 352.47 g/mol. PGD2 is a research tool for studying sleep, inflammation, and allergy. It is not for therapeutic use.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C20H32O5
Molecular Weight
352.46508
Exact Mass
352.224
CAS #
41598-07-6
Related CAS #
Prostaglandin D2-d9;2254642-52-7;Prostaglandin D2-d4;211105-29-2
PubChem CID
448457
Appearance
White to light yellow solid powder
Density
1.1±0.1 g/cm3
Boiling Point
549.6±50.0 °C at 760 mmHg
Melting Point
56 - 57 °C
Flash Point
300.3±26.6 °C
Vapour Pressure
0.0±3.4 mmHg at 25°C
Index of Refraction
1.561
LogP
2.02
Hydrogen Bond Donor Count
3
Hydrogen Bond Acceptor Count
5
Rotatable Bond Count
12
Heavy Atom Count
25
Complexity
469
Defined Atom Stereocenter Count
4
SMILES
CCCCC[C@@H](/C=C/[C@@H]1[C@H]([C@H](CC1=O)O)C/C=C\CCCC(=O)O)O
InChi Key
BHMBVRSPMRCCGG-OUTUXVNYSA-N
InChi Code
InChI=1S/C20H32O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,15-18,21-22H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16+,17+,18-/m0/s1
Chemical Name
(Z)-7-[(1R,2R,5S)-5-hydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]-3-oxocyclopentyl]hept-5-enoic 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

Note: 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)
Solubility Data
Solubility (In Vitro)
Ethanol : ~75 mg/mL (~212.78 mM)
DMSO : ~50 mg/mL (~141.86 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (7.09 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 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL 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: ≥ 2.5 mg/mL (7.09 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 25.0 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 2.8371 mL 14.1856 mL 28.3712 mL
5 mM 0.5674 mL 2.8371 mL 5.6742 mL
10 mM 0.2837 mL 1.4186 mL 2.8371 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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Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
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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.
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