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 (2)
Literature

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.

All Tocris products are intended for laboratory research use only.

Solubility Data

SolubilitySoluble in DMSO and in ethanol

Preparing Stock Solutions

The following data is based on the product molecular weight 454.68. Batch specific molecular weights may vary from batch to batch due to solvent of hydration, which will affect the solvent volumes required to prepare stock solutions.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 2.2 mL 11 mL 21.99 mL
5 mM 0.44 mL 2.2 mL 4.4 mL
10 mM 0.22 mL 1.1 mL 2.2 mL
50 mM 0.04 mL 0.22 mL 0.44 mL

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Product Datasheets

Certificate of Analysis / Product Datasheet
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Safety Datasheet

References

References are publications that support the products' biological activity.

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 PMID:

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

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: EB1089 VDR agonist Vitamin D receptors seocalcitol VDR-like Seocalcitol Vitamin D Receptors

2 Citations for EB 1089

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

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

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


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