An antagonist of the vitamin D receptor
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ZK 159222

Item No. 9001925

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1-[(1R,2E,4R)-4-[(1R,3aS,4E,7aR)-4-[(2Z)-2-[(3S,5R)-3,5-dihydroxy-2-methylenecyclohexylidene]ethylidene]octahydro-7a-methyl-1H-inden-1-yl]-1-hydroxy-2-penten-1-yl]-cyclopropanecarboxylic acid, butyl ester
CAS Number
156965-15-0
Molecular Formula
C32H48O5
Formula Weight
512.7
Purity
≥95%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
Chloroform: Slightly solubleMethanol: Slightly soluble
SMILES
C=C1/C(C[C@@H](O)C[C@@H]1O)=C\C=C2CCC[C@@]3(C)[C@@]/2([H])CC[C@]3([H])[C@H](C)/C=C/[C@@H](O)C4(CC4)C(OCCCC)=O
InChi Code
InChI=1S/C32H48O5/c1-5-6-18-37-30(36)32(16-17-32)29(35)14-9-21(2)26-12-13-27-23(8-7-15-31(26,27)4)10-11-24-19-25(33)20-28(34)22(24)3/h9-11,14,21,25-29,33-35H,3,5-8,12-13,15-20H2,1-2,4H3/b14-9+,23-10+,24-11-/t21-,25-,26-,27+,28+,29-,31-/m1/s1
InChi Key
SPARTCPUGRJFRS-PBDCIXLPSA-N
Shipping & Storage Information
Storage
-80°C
Shipping
Dry ice in continental US; may vary elsewhere
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    500 µg

    $908

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    Product Description

    ZK 159222 is an antagonist of the vitamin D receptor (VDR).1,2 It stabilizes the VDR in an antagonistic conformation that prevents interaction with coactivator proteins.3 ZK 159222 inhibits VDR-mediated target gene activation when used at concentrations of 300 and 1,000 nM in reporter assays. Preincubation of preadipocytes with ZK 159222 (0.01 and 1 µM) decreases the secretion of IL-1β, IL-6, IL-8, CCL2, and RANTES induced by macrophage-conditioned medium (MacCM).4 It also decreases the secretion of these cytokines in preadipocytes prestimulated with MacCM and decreases MacCM-induced phosphorylation of p44/42 and p38 MAPK in preadipocytes.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Herdick, M., Steinmeyer, A., and Carlberg, C. Antagonistic action of a 25-carboxylic ester analogue of 1ɑ,25-dihydroxyvitamin D3 is mediated by a lack of ligand-induced vitamin D receptor interaction with coactivators. The Journal of Biological Chemisty 275(22), 16506-16512 (2000).

    2. Herdick, M., Steinmeyer, A., and Carlberg, C. Carboxylic ester antagonists of 1ɑ,25-dihydroxyvitamin D3 show cell-specific actions. Chem. Biol. 7(11), 885-894 (2000).

    3. Bury, Y., Steinmeyer, A., and Carlberg, C. Structure activity relationship of carboxylic ester antagonists of the vitamin D3 receptor. Mol. Pharmacol. 58(5), 1067-1074 (2000).

    4. Zhu, J., and Wilding, J.P.H. The 1α,25(OH)2D3 analogs ZK159222 and ZK191784 show anti-inflammatory properties in macrophage-induced preadipocytes via modulating the NF-κB and MAPK signaling. Diabetes Metab. Syndr. Obes. 13, 1715-1724 (2020).