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Structure Database (LMSD)

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Common Name

ZK 159222

Systematic Name

(5Z,7E,22E)-(1S,3R,24R)-25-carbobutoxy-26,26-cyclo-9,10-seco-5,7,10(19),22-cholestatetraene-1,3,24-triol

Synonyms

LM ID

LMST03020621

Formula

C₃₂H₄₈O₅

Exact Mass

Calculate m/z

512.350175

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

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.

This information has been provided by Cayman Chemical

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).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

synthetic construct (#32630)

Antagonistic action of a 25-carboxylic ester analogue of 1alpha, 25-dihydroxyvitamin D3 is mediated by a lack of ligand-induced vitamin D receptor interaction with coactivators.,
J Biol Chem, 2000

Pubmed ID: 10748178

String Representations

InChiKey (Click to copy)

SPARTCPUGRJFRS-PBDCIXLPSA-N

InChi (Click to copy)

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

SMILES (Click to copy)

C1/C(=C/C=C2\CCC[C@]3(C)[C@]([C@@]([H])(/C=C/[C@@H](O)C4(CC4)C(=O)OCCCC)C)([H])CC[C@@]\23[H])/C(=C)[C@@H](O)C[C@@H]1O