(5Z)-7-Oxozeaenol

Cat. No. 3604

(5Z)-7-Oxozeaenol C19H22O7 [253863-19-3]

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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.

Certificate of Analysis / Product Datasheet / Safety Datasheet

References are publications that support the products' biological activity.

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

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.

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.

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

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

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 (1) 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.

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.

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.

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.

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.

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

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

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