Catalog Number: 3604
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
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
  • Solubility:
    Soluble to 25 mM in DMSO and to 10 mM in ethanol
  • Purity:
    >98%
  • Storage:
    Desiccate at -20°C
  • CAS No:
    253863-19-3
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.
Background References
  1. A resorcyclic acid lactone, 5Z-7-Oxozeaenol, prevents inflammation by inhibiting the catalytic activity of TAK1 MAPK kinase kinase.
    Ninomiya-Tsuji et al.
    J.Biol.Chem., 2003;278:18485
  2. Blockade of transforming growth factor-β-activated kinase 1 activity enhances TRAIL-induced apoptosis through activation of a caspase cascade.
    Choo et al.
    Mol.Cancer Ther., 2006;5:2970
  3. Molecular mechanisms involved in the regulation of cytokine production by muramyl dipeptide.
    Windheim et al.
    Biochem.J., 2007;404:179
Citations:

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

10 Citations: Showing 1 - 10
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  1. TGFβ1-induced SMAD2/3 and SMAD1/5 phosphorylation are both ALK5-kinase-dependent in primary chondrocytes and mediated by TAK1 kinase activity.
    Authors: van Caam
    Arthritis Research & Therapy 2017;19(1):112
  2. Targeting of TGF-β-activated protein kinase 1 inhibits chemokine (C-C motif) receptor 7 expression, tumor growth and metastasis in breast cancer.
    Authors: Huang Et al.
    Oncotarget 2015;6:995
  3. Stabilization of ATF5 by TAK1-Nemo-like kinase critically regulates the interleukin-1β-stimulated C/EBP signaling pathway.
    Authors: Zhang Et al.
    Nat Commun 2015;35:778
  4. 5Z-7-Oxozeanol Inhibits the Effects of TGFβ1 on Human Gingival Fibroblasts.
    Authors: Kuk Et al.
    PLoS One 2015;10:e0123689
  5. BMP signalling regulates the pre-implantation development of extra-embryonic cell lineages in the mouse embryo.
    Authors: Graham Et al.
    J Biol Chem 2014;5:5667
  6. Inhibition of transglutaminase 2, a novel target for pulmonary fibrosis, by two small electrophilic molecules.
    Authors: Olsen Et al.
    Am J Respir Cell Mol Biol 2014;50:737
  7. Activation of TAK1 by MYD88 L265P drives malignant B-cell Growth in non-Hodgkin lymphoma.
    Authors: Ansell Et al.
    Blood Cancer J 2014;4:e183
  8. Prolonged NF-κB activation by a macrophage inhibitory cytokine 1-linked signal in enteropathogenic Escherichia coli-infected epithelial cells.
    Authors: Choi Et al.
    Infect Immun 2013;81:1860
  9. The E3 ligase Itch and deubiquitinase Cyld act together to regulate Tak1 and inflammation.
    Authors: Ahmed Et al.
    Nat Immunol 2011;12:1176
  10. Phosphorylation of lysophosphatidylcholine acyltransferase 2 at Ser34 enhances platelet-activating factor production in endotoxin-stimulated macrophages.
    Authors: Morimoto Et al.
    Proc Natl Acad Sci U S A 2010;285:29857

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