prostaglandin D2

プロスタグランジンD2 PGD2

WordNet

1. the 4th letter of the Roman alphabet (同)d
2. a potent substance that acts like a hormone and is found in many bodily tissues (and especially in semen); produced in response to trauma and may affect blood pressure and metabolism and smooth muscle activity

PrepTutorEJDIC

1. deuteriumの化学記号

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/03/10 16:00:57」(JST)

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Prostaglandin D2

Names
IUPAC name 9α,15S-dihydroxy-11-oxo-prosta-5Z,13E-dien-1-oic acid
Identifiers
CAS Registry Number	41598-07-6 Y
ChEBI	CHEBI:15555 N
ChemSpider	395250 N
InChI 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 N Key: BHMBVRSPMRCCGG-OUTUXVNYSA-N N InChI=1/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 Key: BHMBVRSPMRCCGG-OUTUXVNYBP
IUPHAR ligand	1891
Jmol-3D images	Image
KEGG	C00696 N
MeSH	Prostaglandin+D2
PubChem	448457
SMILES CCCCC[C@@H](/C=C/[C@@H]1[C@H]([C@H](CC1=O)O)C/C=C\CCCC(=O)O)O
Properties
Molecular formula	C20H32O5
Molar mass	352.465 g/mol
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
N verify (what is: Y/N?)
Infobox references

Prostaglandin D₂ (or PGD₂) is a prostaglandin that binds to the receptor PTGDR, as well as CRTH2. It is a major prostaglandin produced by mast cells – recruits Th2 cells, eosinophils, and basophils. In mammalian organs, large amounts of PGD₂ are found only in the brain and in mast cells. It is critical to development of allergic diseases such as asthma.

Research carried out in 1989 found PGD₂ is the primary mediator of vasodilation (the "niacin flush") after ingestion of niacin (nicotinic acid).

A 2012 research paper indicates a causal link between elevated levels of localized PGD₂ and hair growth inhibition. Applied topically, the researchers found PGD₂ prevents hair growth, and mice that were genetically inclined to produce higher levels of PGD₂ had inhibited hair growth. The researchers also found PGD₂ levels were much higher in balding scalp tissue than nonbalding scalp tissue, through increased levels of prostaglandin D2 synthase. The paper suggested that inhibition of hair growth involved binding of PGD₂ to a receptor called GPR44, and that GPR44 therefore would be a therapeutic target for androgenic alopecia in both men and women with hair loss and thinning. Because PGD₂'s relation to asthma has been known for several years, several drugs that seek to reduce the effect of PGD₂ through blocking the GPR44 are already in clinical trials.

§Production

• Cellular synthesis occurs through the arachidonic acid cascade with the final conversion from PGH₂ done by PGD₂ synthase (PTGDS).
• In the brain, production occurs via an alternative pathway through the soluble, secreted enzyme β-trace

§Effects

• PGD₂ causes a contraction of the bronchial airways. Its concentration in asthma patients is 10 times higher than in control patients, especially after it is brought into contact with allergens.
• It is involved in the regulation of reducing body temperature in sleep, and acts opposite to PGE₂.
• It causes vasodilation.
• Elevated levels of PGD₂ and PGD₂ synthase in scalp hair follicles may be partially responsible for male pattern baldness.
• PGD₂ also plays a part in male sexual development. It forms a feedforward loop with Sox9, which is activated by the SRY of the Y chromosome. PGD2, in a different feedforward loop than FGF9, helps keep the level of SOX9 high enough to activate other genes, such as Fgf9 and Sf1, which are necessary for the development of the male reproductive system

§Latest Research

In August 2012, Scientists at the University of Pennsylvania announced that they had discovered PGD₂ was present on the scalp of balding men at far higher levels than normal, preventing hair follicles from maturing and therefore stopping them from working and growing hair. Dr. George Cotsarelis and his dermatological team at the University say that they are in talks with several pharmaceutical companies about developing treatments which could be available in two years.

§See also

• PGD₂ synthase

§References

UpToDate Contents

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English Journal

• Interleukin-6 potentiates FcεRI-induced PGD2 biosynthesis and induces VEGF from human in situ-matured skin mast cells.

• McHale C1, Mohammed Z2, Deppen J3, Gomez G4.
• Biochimica et biophysica acta.Biochim Biophys Acta.2018 May;1862(5):1069-1078. doi: 10.1016/j.bbagen.2018.01.020. Epub 2018 Feb 2.
• PMID 29410184

• DP1 receptor signaling prevents the onset of intrinsic apoptosis in eosinophils and functions as a transcriptional modulator.

• Peinhaupt M1, Roula D1, Theiler A1, Sedej M1, Schicho R1,2, Marsche G1,2, Sturm EM1, Sabroe I3, Rothenberg ME4, Heinemann A1,2.
• Journal of leukocyte biology.J Leukoc Biol.2018 Apr 1. doi: 10.1002/JLB.3MA1017-404R. [Epub ahead of print]
• PMID 29607536

• Arachidonic Acid Induces ARE/Nrf2-Dependent Heme Oxygenase-1 Transcription in Rat Brain Astrocytes.

• Lin CC1, Yang CC2,3, Chen YW3, Hsiao LD1, Yang CM4,5,6,7.
• Molecular neurobiology.Mol Neurobiol.2018 Apr;55(4):3328-3343. doi: 10.1007/s12035-017-0590-7. Epub 2017 May 11.
• PMID 28497199

Japanese Journal

• Niacin ameliorates ulcerative colitis via prostaglandin D2‐mediated D prostanoid receptor 1 activation

• EMBO molecular medicine 9(5), 571-588, 2017-05
• NAID 120006224674

• Generation and characterization of an antagonistic monoclonal antibody against an extracellular domain of mouse DP2 (CRTH2/GPR44) receptors for prostaglandin D2

• PLOS ONE 12(4), e0175452, 2017-04
• NAID 120006224662

• Prostaglandin D2 Attenuates Bleomycin-Induced Lung Inflammation and Pulmonary Fibrosis

• PLOS ONE 11(12), e0167729, 2016-12
• NAID 120006023321

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