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 ActivityResorcyclic 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.
The technical data provided above is for guidance only.
For batch specific data refer to the Certificate of Analysis.
Tocris products are intended for laboratory research use only, unless stated otherwise.
A resorcyclic acid lactone, 5Z-7-Oxozeaenol, prevents inflammation by inhibiting the catalytic activity of TAK1 MAPK kinase kinase.
Ninomiya-Tsuji et al.
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
Molecular mechanisms involved in the regulation of cytokine production by muramyl dipeptide.
Windheim et al.
Citations for (5Z)-7-Oxozeaenol
The citations listed below are publications that use Tocris products. Selected citations for (5Z)-7-Oxozeaenol include:
24 Citations: Showing 1 - 10
Platelet-derived β2M regulates monocyte inflammatory responses.
Authors: Hilt Et al.
JCI Insight 2019;4
RAC1P29S Induces a Mesenchymal Phenotypic Switch via Serum Response Factor to Promote Melanoma Development and Therapy Resistance.
Authors: Lionarons Et al.
Cancer Cell 2019;36:68
Nemo-like Kinase Drives Foxp3 Stability and Is Critical for Maintenance of Immune Tolerance by Regulatory T Cells.
Authors: Fleskens Et al.
Cell Rep 2019;26:3600
TAK1 mediates microenvironment-triggered autocrine signals and promotes triple-negative breast cancer lung metastasis.
Nat Commun 2018;9(1):1994
Ubiquitin-Mediated Regulation of RIPK1 Kinase Activity Independent of IKK and MK2.
Authors: Annibaldi Et al.
Mol Cell 2018;69:566
Inflammatory but not mitogenic contexts prime synovial fibroblasts for compensatory signaling responses to p38 inhibition.
Authors: Jones Et al.
Sci Signal 2018;11
Central Administration of 5Z-7-Oxozeaenol Protects Experimental Autoimmune Encephalomyelitis Mice by Inhibiting Microglia Activation.
Authors: Lu Et al.
Front Pharmacol 2017;8:789
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.
Authors: Ismail Et al.
Arthritis Rheumatol 2017;69:565
MK2 Phosphorylates RIPK1 to Prevent TNF-Induced Cell Death.
Authors: Jaco Et al.
Mol Cell 2017;66:698
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
Expression and function of transforming growth factor?β?activated protein kinase 1 in gastric cancer.
Authors: Yang Et al.
Mol Med Rep 2017;16:3103
Profiling drugs for rheumatoid arthritis that inhibit synovial fibroblast activation.
Authors: Jones Et al.
Nat Chem Biol 2017;13:38
p38 (Mapk14/11) occupies a regulatory node governing entry into primitive endoderm differentiation during preimplantation mouse embryo development.
Open Biol 2016;6
Identification of therapeutic targets applicable to clinical strategies in ovarian cancer.
Authors: Kim Et al.
BMC Cancer 2016;16:678
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.
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
5Z-7-Oxozeanol Inhibits the Effects of TGFβ1 on Human Gingival Fibroblasts.
Authors: Kuk Et al.
PLoS One 2015;10:e0123689
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
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
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
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
Protection from cerebral ischemia by inhibition of TGFβ-activated kinase.
Authors: White Et al.
Exp Neurol 2012;237:238
The E3 ligase Itch and deubiquitinase Cyld act together to regulate Tak1 and inflammation.
Authors: Ahmed Et al.
Nat Immunol 2011;12:1176
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
No product specific FAQs exist for this product, however you mayView all Small Molecule FAQs
Reviews for (5Z)-7-Oxozeaenol
Average Rating: 5 (Based on 2 Reviews)
Have you used (5Z)-7-Oxozeaenol?
Submit a review and receive an Amazon gift card.
$25/€18/£15/$25CAN/¥75 Yuan/¥1250 Yen for a review with an image
$10/€7/£6/$10 CAD/¥70 Yuan/¥1110 Yen for a review without an image
Works great for kinase assay. This was tested in TAK1 in vitro kinase assay.
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.