EB 1089

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Cat.No. 3993 - EB 1089 | C30H46O3 | CAS No. 134404-52-7
Description: Vitamin D receptor (VDR) agonist
Alternative Names: Seocalcitol
Chemical Name: (1R,3S,5Z)-5-[(2E)-2-[(1R,3aS,7aR)-1-[(1R,2E,4E)-6-Ethyl-6-hydroxy-1-methyl-2,4-octadien-1-yl]-octahydro-7α-methyl-4H-inden-4-ylidene]ethylidene]-4-methylene-1,3-cyclohexanediol
Purity: ≥98% (HPLC)
Datasheet
Citations (3)
Reviews
Literature (2)

Biological Activity

Vitamin D receptor (VDR) agonist; analog of calcitriol (Cat. No. 2551). Exhibits anti-tumor and anti-proliferative activity with reduced hypercalcemic effects. 60 times more potent in inhibiting MCF-7 cell growth in vitro; also shown to induce autophagy in MCF-7 cells. Reverses the effects of parathyroid hormone-related protein (PTHrP).

Technical Data

M. Wt 454.68
Formula C30H46O3
Storage Store at -20°C
Purity ≥98% (HPLC)
CAS Number 134404-52-7
PubChem ID 5288149
InChI Key LVLLALCJVJNGQQ-SEODYNFXSA-N
Smiles C[C@@](CCC2)3[C@](CC[C@@]([H])3[C@@H](/C=C/C=C/C(CC)(O)CC)C)([H])/C2=C/C=C(C[C@@H](O)C[C@@H]1O)\C1=C

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

Tocris products are intended for laboratory research use only, unless stated otherwise.

Solubility Data

Solubility Soluble in DMSO and in ethanol

Product Datasheets

Certificate of Analysis / Product Datasheet
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References

References are publications that support the biological activity of the product.

Lu et al (2008) Vitamin D3 analogue EB1089 inhibits the proliferation of human laryngeal squamous carcinoma cells via p57. Mol.Cancer Ther. 7 1268 PMID: 18483314

Bhatia et al (2009) EB1089 inhibits the parathyroid hormone-related protein-enhanced bone metastasis and xenograft growth of human prostate cancer cells. Mol.Cancer Ther. 8 1787 PMID: 19584236

Abdaimi et al (1999) Reversal of hypercalcaemia with the vitamin D analogue EB1089 in a human model of squamous cancer. Cancer Res, 59 3325

Ormerod et al (2008) The calci. analogue EB1089 impairs alveolarization and induces localized regions of increased fibroblast density in neonatal rat lung. Exp.Lung.Rs. 34 155

Hoyer-Hansen et al (2005) Vitamin D analog EB1089 triggers dramatic lysosomal changes and Beclin 1-mediated autophagic cell death. Cell Death Differ. 12 1297 PMID: 15905882


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Keywords: EB 1089, EB 1089 supplier, EB1089, VDR, agonist, Vitamin, D, receptors, seocalcitol, VDR-like, Seocalcitol, Receptors, Autophagy, 3993, Tocris Bioscience

3 Citations for EB 1089

Citations are publications that use Tocris products. Selected citations for EB 1089 include:

Solomon et al (2014) VDR activity is differentially affected by Hic-5 in prostate cancer and stromal cells. Mol Cancer Res 12 1166 PMID: 24825850

Sharma et al (2015) A novel cytostatic form of autophagy in sensitization of non-small cell lung cancer cells to radiation by vitamin D and the vitamin D analog, EB 1089. Oncotarget 10 2346 PMID: 25629933

Hiranuma et al (2016) Expression of nephronectin is enhanced by 1α,25-dihydroxyvitamin D3. FEBS Open Bio 6 914 PMID: 27642554


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