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
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. Cell83803-812(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. Biochemistry293760-3765(1990).
3
Shibata, T., Yamada, T., Ishii, T., et al. Thioredoxin as a molecular target of cyclopentenone prostaglandins. J Biol Chem278(28)26046-26054(2003).
Synonyms
9,10-dihydro-15-deoxy-Δ12,14-Prostaglandin J2
9,10-dihydro-15-deoxy-Δ12,14-PGJ2
Formal Name
11-oxo-prosta-5Z,12E,14Z-trien-1-oic acid
CAS Number
596104-94-8
Molecular Formula
C20H30O3
Formula Weight
318.5
Formulation
A solution in methyl acetate
Purity
>98% (isomer mixture)
λmax
293 nm
Stability
1 year
Storage
-20°C
Shipping
Room temperature
in continental US; may vary elsewhere
SMILES
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CCCCC/C=C\C=C1\C(C/C=C\CCCC(=O)O)CCC/1=O
Background Reading
Forman, B.M., Tontonoz, P., Chen, J., et al. 15-Deoxy-Δ12,14-prostaglandin J2 is a ligand for the adipocyte determination factor PPARγ. Cell83803-812(1995).
Shibata, T., Yamada, T., Ishii, T., et al. Thioredoxin as a molecular target of cyclopentenone prostaglandins. J Biol Chem278(28)26046-26054(2003).
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. Biochemistry293760-3765(1990).
CAY10410 is available in the following screening
library: