(5Z)-7-Oxozeaenol

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Cat.No. 3604 - (5Z)-7-Oxozeaenol | C19H22O7 | CAS No. 253863-19-3
Description: Potent and selective TAK1 MAPKKK inhibitor
Chemical Name: (3S,5Z,8S,9S,11E)-3,4,9,10-tetrahydro-8,9,16-trihydroxy-14-methoxy-3-methyl-1H-2-benzoxacyclotetradecin-1,7(8H)-dione
Purity: ≥98% (HPLC)
Datasheet
Citations (19)
Reviews (1)
Literature

Biological Activity

Resorcyclic lactone of fungal origin that acts as a potent and selective transforming growth factor-β-activated kinase 1 (TAK1) mitogen-activated protein kinase kinase kinase (MAPKKK) inhibitor (IC50 = 8 nM). Displays > 33-fold and > 62-fold selectivity over MEKK1 and MEKK4 respectively. Inhibits IL-1-induced activation of NF-κB (IC50 = 83 nM) and JNK/p38. Inhibits production of inflammatory mediators, and sensitizes cells to TRAIL- and TNF-α-induced apoptosis in vitro.

Technical Data

M. Wt 362.37
Formula C19H22O7
Storage Desiccate at -20°C
Purity ≥98% (HPLC)
CAS Number 253863-19-3
PubChem ID 9799061
InChI Key NEQZWEXWOFPKOT-ULSULSEOSA-N
Smiles O=C/2[C@@H](O)[C@@H](O)C/C=C/C1=CC(OC)=CC(O)=C1C(O[C@@H](C)C\C=C2)=O

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

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 9.06 25
ethanol 3.62 10

Preparing Stock Solutions

The following data is based on the product molecular weight 362.37. 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.

Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
0.25 mM 11.04 mL 55.19 mL 110.38 mL
1.25 mM 2.21 mL 11.04 mL 22.08 mL
2.5 mM 1.1 mL 5.52 mL 11.04 mL
12.5 mM 0.22 mL 1.1 mL 2.21 mL

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Product Datasheets

Certificate of Analysis / Product Datasheet
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References

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

Ninomiya-Tsuji et al (2003) A resorcyclic acid lactone, 5Z-7-Oxozeaenol, prevents inflammation by inhibiting the catalytic activity of TAK1 MAPK kinase kinase. J.Biol.Chem. 278 18485 PMID: 12624112

Choo et al (2006) Blockade of transforming growth factor-β-activated kinase 1 activity enhances TRAIL-induced apoptosis through activation of a caspase cascade. Mol.Cancer Ther. 5 2970 PMID: 17172402

Windheim et al (2007) Molecular mechanisms involved in the regulation of cytokine production by muramyl dipeptide. Biochem.J. 404 179 PMID: 17348859


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Keywords: (5Z)-7-Oxozeaenol, (5Z)-7-Oxozeaenol supplier, Potent, selective, TAK1, MAPKKK, inhibitors, inhibits, Kinases, Other, 3604, Tocris Bioscience

19 Citations for (5Z)-7-Oxozeaenol

Citations are publications that use Tocris products. Selected citations for (5Z)-7-Oxozeaenol include:

Iriondo (2018) TAK1 mediates microenvironment-triggered autocrine signals and promotes triple-negative breast cancer lung metastasis. Nat Commun 9 1994 PMID: 29777109

Graham et al (2014) BMP signalling regulates the pre-implantation development of extra-embryonic cell lineages in the mouse embryo. J Biol Chem 5 5667 PMID: 25514175

Ismail et al (2017) Rapid Activation of Transforming Growth Factor β-Activated Kinase 1 in Chondrocytes by Phosphorylation and K(63) -Linked Polyubiquitination Upon Injury to Animal Articular Cartilage. Arthritis Rheumatol 69 565 PMID: 27768832

Jones et al (2017) Profiling drugs for rheumatoid arthritis that inhibit synovial fibroblast activation. Nat Chem Biol 13 38 PMID: 27820799

Jaco et al (2017) MK2 Phosphorylates RIPK1 to Prevent TNF-Induced Cell Death. Mol Cell 66 698 PMID: 28506461

Yang et al (2017) Expression and function of transforming growth factor?β?activated protein kinase 1 in gastric cancer. Mol Med Rep 16 3103 PMID: 28714004

van Caam (2017) TGFβ1-induced SMAD2/3 and SMAD1/5 phosphorylation are both ALK5-kinase-dependent in primary chondrocytes and mediated by TAK1 kinase activity. Arthritis Research & Therapy 19 112 PMID: 28569204

Choi et al (2013) Prolonged NF-κB activation by a macrophage inhibitory cytokine 1-linked signal in enteropathogenic Escherichia coli-infected epithelial cells. Infect Immun 81 1860 PMID: 23403560

Lu et al (2017) Central Administration of 5Z-7-Oxozeaenol Protects Experimental Autoimmune Encephalomyelitis Mice by Inhibiting Microglia Activation. Front Pharmacol 8 789 PMID: 29163172

Zhang et al (2015) Stabilization of ATF5 by TAK1-Nemo-like kinase critically regulates the interleukin-1β-stimulated C/EBP signaling pathway. Nat Commun 35 778 PMID: 25512613

Ahmed et al (2011) The E3 ligase Itch and deubiquitinase Cyld act together to regulate Tak1 and inflammation. Nat Immunol 12 1176 PMID: 22057290

Thamodaran (2016) p38 (Mapk14/11) occupies a regulatory node governing entry into primitive endoderm differentiation during preimplantation mouse embryo development. Open Biol 6 PMID: 27605380

Morimoto et al (2010) Phosphorylation of lysophosphatidylcholine acyltransferase 2 at Ser34 enhances platelet-activating factor production in endotoxin-stimulated macrophages. Proc Natl Acad Sci U S A 285 29857 PMID: 20663880

Kim et al (2016) Identification of therapeutic targets applicable to clinical strategies in ovarian cancer. BMC Cancer 16 678 PMID: 27558154

Huang et al (2015) Targeting of TGF-β-activated protein kinase 1 inhibits chemokine (C-C motif) receptor 7 expression, tumor growth and metastasis in breast cancer. Oncotarget 6 995 PMID: 25557171

Kuk et al (2015) 5Z-7-Oxozeanol Inhibits the Effects of TGFβ1 on Human Gingival Fibroblasts. PLoS One 10 e0123689 PMID: 25927238

White et al (2012) Protection from cerebral ischemia by inhibition of TGFβ-activated kinase. Exp Neurol 237 238 PMID: 22683931

Olsen et al (2014) Inhibition of transglutaminase 2, a novel target for pulmonary fibrosis, by two small electrophilic molecules. Am J Respir Cell Mol Biol 50 737 PMID: 24175906

Ansell et al (2014) Activation of TAK1 by MYD88 L265P drives malignant B-cell Growth in non-Hodgkin lymphoma. Blood Cancer J 4 e183 PMID: 24531446


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Great inhibitor for TAK1 signaling
By Anonymous on 12/04/2017
Assay Type: In Vitro
Species: Mouse
Cell Line/Tissue: Primary human small airway epithelial cells

Primary human small airway epithelial cells were incubated with TAK1 inhibitor prior to the addition of poly(I:C). The supernatant was collected and analyzed for IL-6.

PMID: 25320283
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