A potent, selective EP4 agonist
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CAY10684

Item No. 15966

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2R)-2-[(1E)-3-(4'-chloro-2'-methyl[1,1'-biphenyl]-3-yl)-3-hydroxy-1-propen-1-yl]-5-oxo-1-pyrrolidineheptanoic acid
CAS Number
493035-81-7
Molecular Formula
C27H32ClNO4
Formula Weight
470.0
Purity
≥98%
Formulation
A 5 mg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 17 mg/mlEthanol: 50 mg/mlPBS (pH 7.2): 3 mg/ml
λmax
241 nm
SMILES
O=C1N(CCCCCCC(O)=O)[C@@H](/C=C/C(O)C2=CC(C(C=C3)=C(C)C=C3Cl)=CC=C2)CC1
InChi Code
InChI=1S/C27H32ClNO4/c1-19-17-22(28)10-13-24(19)20-7-6-8-21(18-20)25(30)14-11-23-12-15-26(31)29(23)16-5-3-2-4-9-27(32)33/h6-8,10-11,13-14,17-18,23,25,30H,2-5,9,12,15-16H2,1H3,(H,32,33)/b14-11+/t23-,25?/m0/s1
InChi Key
LMJHPADNCZPRCN-KSPGTVSPSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    500 µg

    $94

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    1 mg

    $179

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    5 mg

    $609

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    10 mg

    $1,029

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    Product Description

    Prostaglandin E2 (PGE2; Item No. 14010) activates four E prostanoid (EP) receptors, EP1-4. EP4 is a G protein-coupled receptor that, by elevating the second messenger cAMP, plays important roles in bone formation and resorption, cancer, and atherosclerosis.1,2,3 CAY10684 is a lactam that acts as a potent EP4 agonist, triggering cAMP signaling with an EC50 value of 0.8 nM.4 It displays more than 1,000-fold selectivity for EP4 over other EP receptors.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Li, M., Thompson, D.D., and Paralkar, V.M. Prostaglandin E2 receptors in bone formation. Int. Orthop. 31(6), 767-772 (2007).

    2. Hawcroft, G., Ko, C.W.S., and Hull, M.A. Prostaglandin E2-EP4 receptor signalling promotes tumorigenic behaviour of HT-29 human colorectal cancer cells. Oncogene 26(21), 3006-3019 (2007).

    3. Babaev, V.R., Chew, J.D., Ding, L., et al. Macrophage EP4 deficiency increases apoptosis and suppresses early atherosclerosis. Cell Metab. 8(6), 492-501 (2008).

    4. Elworthy, T.R., Kertesz, D.J., Kim, W., et al. Lactams as EP4 prostanoid receptor subtype selective agonists. Part 1: 2-Pyrrolidinones-sterochemical and lower side-chain optimization. Bioorg. Med. Chem. Lett. 14(7), 1655-1659 (2004).

    Product Citations

    Matsumoto, N., Singh, N., Lee, K.S., et al. The epoxy fatty acid pathway enhances cAMP in mammalian cells through multiple mechanisms. Prostaglandins Other Lipid Mediat. 162, 106662 (2022).