CRTH2/DP2 agonist
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13,14-dihydro-15-keto Prostaglandin D2

Item No. 12610

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
9α-hydroxy-11,15-dioxo-prost-5Z-en-1-oic acid
CAS Number
59894-07-4
Synonyms
  • 13,14-dihydro-15-keto PGD2
Molecular Formula
C20H32O5
Formula Weight
352.5
Purity
≥95%
Formulation (Request formulation change)
A 10 mg/ml solution in methyl acetate
Solubility(Learn about Variance in Solubility)
DMF: 50 mg/mlDMSO: 30 mg/mlEthanol: 50 mg/mlPBS pH 7.2: 2.5 mg/ml
SMILES
O[C@@H](C1)[C@H](C/C=C\CCCC(O)=O)[C@@H](CCC(CCCCC)=O)C1=O
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/h4,7,16-18,22H,2-3,5-6,8-14H2,1H3,(H,24,25)/b7-4-/t16-,17-,18+/m1/s1
InChi Key
VSRXYLYXIXYEST-KZTWKYQFSA-N
Shipping & Storage Information
Storage
-80°C
Shipping
Dry ice in continental US; may vary elsewhere
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    1 mg

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    Product Description

    13,14-dihydro-15-keto Prostaglandin D2 (13,14-dihydro-15-keto PGD2) is a metabolite of PGD2 (Item No. 12010) which is formed through the 15-hydroxy PGDH pathway. 13,14-dihydro-15-keto PGD2 was recently identified as a selective agonist for the CRTH2/DP2 receptor.1 It also inhibits ion flux in a canine colonic mucosa preparation.2 In humans, 13,14-dihydro-15-keto PGD2 is further metabolized to give 11β-hydroxy compounds which have also undergone β-oxidation of one or both side chains. Virtually no 13,14-dihydro-15-keto PGD2 survives intact in the urine.3,4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Rangachari, P.K., and Betti, P.A. Biological activity of metabolites of PGD2 on canine proximal colon. Am. J. Physiol. 264(5 Pt 1), G886-G894 (1993).

    2. 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).

    3. Liston, T.E., and Roberts, L.J., II Metabolic fate of radiolabeled prostaglandin D2 in a normal human male volunteer. The Journal of Biological Chemisty 260(24), 13172-13180 (1985).

    4. Morrow, J.D., Prakash, C., Awad, J.A., et al. Quantification of the major urinary metabolite of prostaglandin D2 by a stable isotope dilution mass spectrometric assay. Anal. Biochem. 193(1), 142-148 (1991).

    Product Citations

    Meriwether, D., Sulaiman, D., Volpe, C., et al. Apolipoprotein A-I mimetics mitigate intestinal inflammation in COX2-dependent inflammatory bowel disease model. J. Clin. Invest. 130, 3670-3685 (2019).

    Gomez-Abellan, V., Montero, J., Lopez-Munoz, A., et al. Professional phagocytic granulocyte-derived PGD2 regulates the rsolution of inflammation in fish. Develop. Comp. Immunol. 52(2), 182-191 (2015).

    Schröder, R., Xue, L., Konya, V., et al. PGH1, the precursor for the anti-inflammatory prostaglandins of the 1-series, is a potent activator of the pro-inflammatory receptor CRTH2/DP2. PLoS One 7(3), e33329 (2012).