A less electrophilic, isosteric analog of 15-deoxy-D12,14-PGJ2
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CAY10410

Item No. 18590

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
11-oxo-prosta-5Z,12E,14Z-trien-1-oic acid
CAS Number
596104-94-8
Synonyms
  • 9,10-dihydro-15-deoxy-Δ12,14-PGJ2
  • 9,10-dihydro-15-deoxy-Δ12,14-Prostaglandin J2
Molecular Formula
C20H30O3
Formula Weight
318.5
Purity
≥98% (mixture of isomers)
Formulation
A 5 mg/ml solution in methyl acetate
Solubility(Learn about Variance in Solubility)
DMF: 100 mg/mlDMSO: 20 mg/mlEthanol: 75 mg/mlPBS (7.2): 2.7 mg/ml
λmax
293 nm
SMILES
O=C1/C([C@@H](C/C=C\CCCC(O)=O)CC1)=C/C=C\CCCCC
InChi Code
InChI=1S/C20H30O3/c1-2-3-4-5-6-10-13-18-17(15-16-19(18)21)12-9-7-8-11-14-20(22)23/h6-7,9-10,13,17H,2-5,8,11-12,14-16H2,1H3,(H,22,23)/b9-7-,10-6-,18-13+/t17-/m0/s1
InChi Key
AFBJLDUEEOOVHL-WKELIDJCSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

    $98

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    1 mg

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    5 mg

    $882

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    Product Description

    CAY10410 is an analog of prostaglandin D2/prostaglandin J2 (PGD2/PGJ2) with structural modifications intended to give it PPARγ ligand activity and resistance to metabolism. 15-deoxy-Δ12,14-PGJ2 has been shown to be a potent ligand for PPARγ.1 Metabolism of the cyclopentenone prostaglandins PGA2, PGJ2, and Δ12-PGJ2 occurs via glutathione addition across the α,β unsaturated enone.2 CAY10410 was designed as an analog of the PPARγ-binding prostaglandins which could not undergo this conjugation reaction. In human neuroblastoma SH-SY5Y cells, CAY10410 was not cytotoxic at up to 25 µM. It also failed to covalently modify thioredoxin or induce oxidative stress at 50 µM.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. 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).

    2. Atsmon, J., Sweetman, B.J., Baertschi, S.W., et al. Formation of thiol conjugates of 9-deoxy-Δ9,Δ12(E)-prostaglandin D2 and Δ12(E)-prostaglandin D2. Biochemistry 29(15), 3760-3765 (1990).

    3. Shibata, T., Yamada, T., Ishii, T., et al. Thioredoxin as a molecular target of cyclopentenone prostaglandins. The Journal of Biological Chemisty 278(28), 26046-26054 (2003).