PROSTAGLANDIN D2 Chemical Properties

Melting point:

68°C

Boiling point:

406.07°C (rough estimate)

alpha 

+7.5°(D/21℃)(c=1,THF)

Density 

1.0601 (rough estimate)

refractive index 

1.6120 (estimate)

storage temp. 

-20°C

solubility 

Chloroform (Slightly), Ethanol (Slightly), Methanol (Slightly), THF (Slightly)

pka

4.76±0.10(Predicted)

form 

White solid

color 

White to Light Orange

biological source

synthetic

BRN 

2170623

Stability:

Light Sensitive

Safety Information

Hazard Codes 

T

Risk Statements 

60-22

Safety Statements 

53-22-26-36

WGK Germany 

3

RTECS 

UK7930000

F 

10

MSDS

• Language:English Provider:SigmaAldrich

PROSTAGLANDIN D2 Usage And Synthesis

Description

Prostaglandin D₂ (PGD₂) is the major eicosanoid product of mast cells and is released in large quantities during allergic and asthmatic anaphylaxis. Mastocytosis patients produce excessive amounts of PGD₂, which causes vasodilation, flushing, hypotension, and syncopal episodes. PGD₂ is also produced in the brain via an alternative pathway involving a soluble, secreted PGD-synthase also known as β-trace. In the brain, PGD₂ produces normal physiological sleep and lowering of body temperature. Further pharmacological actions include inhibition of platelet aggregation and relaxation of vascular smooth muscle. PGD₂ inhibits human ovarian tumor cell proliferation with an IC₅₀ of 6.8 μM.

Uses

Prostaglandin D2 is a fatty acid compound present in the human body. Elevated levels of localized Prostaglandin D2 has been linked to hair loss and growth inhibition. It has also been seen to contribute to the activity of allergic asthma.

Definition

ChEBI: A member of the class of prostaglandins D that is prosta-5,13-dien-1-oic acid substituted by hydroxy groups at positions 9 and 15 and an oxo group at position 11 (the 5Z,9alpha,13E,15S- s ereoisomer).

Biochem/physiol Actions

Primary prostaglandin in brain; induces inflammation; stimulates adenylyl cyclase.

in vivo

IC 50

DP; Human Endogenous Metabolite

References

[1] L.JACKSON ROBERTS II  Brian J S. Metabolic fate of endogenously synthesized prostaglandin D2 in a human female with mastocytosis[J]. Prostaglandins, 1985, 30 3: Pages 383-400. DOI: 10.1016/0090-6980(85)90114-5
[2] HAYAISHI O. Sleep-wake regulation by prostaglandins D2 and E2.[J]. The Journal of Biological Chemistry, 1988, 263 29: 14593-14596.
[3] H ONOE. Prostaglandin D2, a cerebral sleep-inducing substance in monkeys.[J]. Proceedings of the National Academy of Sciences of the United States of America, 1988, 85 11: 4082-4086. DOI: 10.1073/pnas.85.11.4082
[4] Y KIKUCHI. Preclinical studies of antitumor prostaglandins by using human ovarian cancer cells.[J]. Cancer and Metastasis Reviews, 1994, 13 3-4: 309-315. DOI: 10.1007/bf00666101
[5] BRENDAN J. WHITTLE . Binding and activity of the prostacyclin receptor (IP) agonists, treprostinil and iloprost, at human prostanoid receptors: Treprostinil is a potent DP1 and EP2 agonist[J]. Biochemical pharmacology, 2012, 84 1: Pages 68-75. DOI: 10.1016/j.bcp.2012.03.012
[6] OYEBOLA O OYESOLA. The Prostaglandin D2 Receptor CRTH2 Promotes IL-33-Induced ILC2 Accumulation in the Lung.[J]. Journal of immunology, 2020, 204 4: 1001-1011. DOI: 10.4049/jimmunol.1900745
[7] AKIKO SUGANAMI. Human DP and EP2 prostanoid receptors take on distinct forms depending on the diverse binding of different ligands[J]. The FEBS journal, 2016, 283 21: 3931-3940. DOI: 10.1111/febs.13899
[8] D F WOODWARD. Pharmacological characterization of a novel antiglaucoma agent, Bimatoprost (AGN 192024).[J]. Journal of Pharmacology and Experimental Therapeutics, 2003, 305 2: 772-785. DOI: 10.1124/jpet.102.047837
[9] P. WAFFO-TéGUO. Potential Cancer-Chemopreventive Activities of Wine Stilbenoids and Flavans Extracted From Grape (Vitis vinifera) Cell Cultures[J]. Nutrition and Cancer-An International Journal, 2001, 40 1: 173-179. DOI: 10.1207/s15327914nc402_14

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