| Identification | Back Directory | [Name]
15(R)-PROSTAGLANDIN D2 | [CAS]
59894-05-2 | [Synonyms]
15(R)-PROSTAGLANDIN D2
BHMBVRSPMRCCGG-DFVNJMEGSA-N
9ALPHA,15R-DIHYDROXY-11-OXO-PROSTA-5E,13E-DIEN-1-OIC ACID | [Molecular Formula]
C20H32O5 | [MDL Number]
MFCD18432679 | [MOL File]
59894-05-2.mol | [Molecular Weight]
352.47 |
| Chemical Properties | Back Directory | [Boiling point ]
549.6±50.0 °C(Predicted) | [density ]
1.148±0.06 g/cm3(Predicted) | [solubility ]
DMF: 50 mg/ml; DMSO: 50 mg/ml; Ethanol: 50 mg/ml; PBS (pH 7.4): 1 mg/ml | [form ]
Liquid | [pka]
4.76±0.10(Predicted) | [color ]
Colorless to light yellow |
| Hazard Information | Back Directory | [Description]
Many of the effects of prostaglandin D2 (PGD2) are transduced via a traditional 7-transmembrane GPCR, the DP1 receptor.1 However, in certain leukocytes and other immune cells, a second PGD2 receptor referred to as the CRTH2 or DP2 receptor has been cloned and characterized.2,3 15(R)-15-methyl PGD2 is a surprisingly potent agonist at the DP2 receptor, being about 5 times more potent than PGD2 itself.4 15(R)-PGD2 has the potential to be produced endogenously as a natural ligand for DP2, unlike the synthetic 15-methyl analogs. In preliminary reports, 15(R)-PGD2 has also been reported to be a potent and selective DP2 receptor agonist.5,6 | [Uses]
15(R)-Prostaglandin D2 is a potential prostatic hormone DP(2) receptor (Prostaglandin Receptor) agonist with anti-inflammatory activity. 15(R)-Prostaglandin D2 increases actin polymerization in human eosinophils and increases cAMP levels in platelets[1]. | [Definition]
ChEBI: 15R-PGD2 is a prostanoid. | [References]
1. Boie, Y., Sawyer, N., Slipetz, D.M., et al. Molecular cloning and characterization of the human prostanoid DP receptor J. Biol. Chem. 270(32),18910-18916(1995).
2. Abe, H., Takeshita, T., Nagata, K., et al. Molecular cloning, chromosome mapping and characterization of the mouse CRTH2 gene, a putative member of the leukocyte chemoattractant receptor family Gene 227,71-77(1999).
3. Hirai, H., Tanaka, K., Yoshie, O., et al. Prostaglandin D2 selectivity induces chemotaxis in T helper type 2 cells, eosinophils, and basophils via seven-transmembrane receptor CRTH2 J. Exp. Med. 193(2),255-261(2001).
4. Monneret, G., Cossette, C., Gravel, S., et al. 15R-methyl-prostaglandin D2 is a potent and selective CRTH2/DP2 receptor agonist in human eosinophils J. Pharmacol. Exp. Ther. 304(1),349-355(2003).
5. Kim, S., Bellone, S., Maxey, K.M., et al. Synthesis of 15R-PGD2: A potential DP2 receptor agonist Bioorg. Med. Chem. Lett. 15(7),1873-1876(2005).
6. Cossette, C., Walsh, S.E., Kim, S., et al. Agonist and antagonist effects of 15R-prostaglandin (PF) D2 and 11-methylene-PGD2 on human eosinophils and basophils J. Pharmacol. Exp. Ther. 320(1),173-179(2007). |
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