A metabolite of PGD2 and an agonist of DP2
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15-deoxy-Δ12,14-Prostaglandin D2

Item No. 12700

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
9α-hydroxy-11-oxo-prosta-5Z,12E,14E-trien-1-oic acid
CAS Number
85235-11-6
Synonyms
  • 15-deoxy-Δ12,14-PGD2
Molecular Formula
C20H30O4
Formula Weight
334.5
Purity
≥95%
Formulation (Request formulation change)
A 1 mg/ml solution in methyl acetate
Solubility(Learn about Variance in Solubility)
DMF: 50 mg/mlDMSO: 50 mg/mlEthanol: 50 mg/mlPBS pH 7.2: 5 mg/ml
λmax
296 nm
SMILES
O=C1/C([C@@H](C/C=C\CCCC(O)=O)[C@@H](O)C1)=C/C=C/CCCCC
InChi Code
InChI=1S/C20H30O4/c1-2-3-4-5-6-9-12-16-17(19(22)15-18(16)21)13-10-7-8-11-14-20(23)24/h6-7,9-10,12,17,19,22H,2-5,8,11,13-15H2,1H3,(H,23,24)/b9-6+,10-7-,16-12+/t17-,19+/m1/s1
InChi Key
QUGBPWLPAUHDTI-PLGLXCLHSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    500 µg

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    Product Description

    15-deoxy-Δ12,14-PGD2 is a metabolite of PGD2 (Item No. 12010).1 It is an agonist of PGD2 receptor 2 (DP2) that binds DP2 (Ki = 50 nM for the mouse receptor expressed in HEK293 cell membranes) and induces activation of eosinophils (EC50 = 8 nM).2,3 It also stimulates the recruitment of steroid receptor coactivator-1 (SRC-1) to peroxisome proliferator-activated receptor γ (PPARγ) and induces PPARγ-mediated transcription in a reporter assay when used at a concentration of 5 µM.1 15-deoxy-Δ12,14-PGD2 is cytotoxic to L1210 murine leukemia cells (IC50 = 0.3 µg/ml).4 It inhibits ADP-induced platelet aggregation (IC50 = 320 ng/ml) less potently than PGD2.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Söderström, M., Wigren, J., Surapureddi, S., et al. Novel prostaglandin D2-derived activators of peroxisome proliferator-activated receptor-γ are formed in macrophage cell cultures. Biochim. Biophys. Acta 1631(1), 35-41 (2003).

    2. Hata, A.N., Zent, R., Breyer, M.D., et al. Expression and molecular pharmacology of the mouse CRTH2 receptor. J. Pharmacol. Exp. Ther. 306(2), 463-470 (2003).

    3. Monneret, G., Li, H., Vasilescu, J., et al. 15-Deoxy-Δ12,14-prostaglandins D2 and J2 are potent activators of human eosinophils. J. Immunol. 168(7), 3563-3569 (2002).

    4. Forman, B.M., Tontonoz, P., Chen, J., et al. 15-Deoxy-Δ12,14-prostaglandin J2 is a ligand for the adipocyte determination factor PPARγ. Cell 83(5), 803-812 (1995).

    5. Bundy, G.L., Morton, D.R., Peterson, D.C., et al. Synthesis and platelet aggregation inhibiting activity of prostaglandin D analogues. J. Med. Chem. 26(6), 790-799 (1983).