(5Z)-7-Oxozeaenol

Pricing Availability Delivery Time Qty
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 (10)
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.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 2.76 mL 13.8 mL 27.6 mL
5 mM 0.55 mL 2.76 mL 5.52 mL
10 mM 0.28 mL 1.38 mL 2.76 mL
50 mM 0.06 mL 0.28 mL 0.55 mL

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

Product Datasheets

Certificate of Analysis / Product Datasheet
Select another batch:
Safety Datasheet

References

References are publications that support the products' biological activity.

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


If you know of a relevant reference for (5Z)-7-Oxozeaenol, please let us know.

View Related Products by Target

View Related Products by Product Action

View all Other Kinase Inhibitors

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

10 Citations for (5Z)-7-Oxozeaenol

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

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

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

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

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

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

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

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

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


Do you know of a great paper that uses (5Z)-7-Oxozeaenol from Tocris? If so please let us know.

Commented out for usability testing

Reviews

TODO: Add Reviews

Literature in this Area

Cancer

Cancer Research Product Guide

A collection of over 750 products for cancer research, the guide includes research tools for the study of:

  • Cancer Metabolism
  • Epigenetics in Cancer
  • Receptor Signaling
  • Cell Cycle and DNA Damage Repair
  • Angiogenesis
  • Invasion and Metastasis
Kinases

Kinases Product Listing

A collection of over 400 products for kinase research, the listing includes inhibitors of:

  • Receptor Tyrosine Kinases
  • Protein Kinases A, C, D and G
  • PI-3 Kinase, Akt and mTOR
  • MAPK Signaling
  • Receptor Serine/Threonine Kinases

Pathways for (5Z)-7-Oxozeaenol

Protocols

TODO: Add Protocols