(5Z)-7-Oxozeaenol

Catalog # Availability Size / Price Qty
3604/1
(5Z)-7-Oxozeaenol | CAS No. 253863-19-3 | Other Kinase Inhibitors
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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%

Product Details
Citations (24)
Reviews (2)

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.
Tocris products are intended for laboratory research use only, unless stated otherwise.

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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

  1. Platelet-derived β2M regulates monocyte inflammatory responses.
    Authors: Hilt Et al.
    JCI Insight  2019;4
  2. 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
  3. 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
  4. TAK1 mediates microenvironment-triggered autocrine signals and promotes triple-negative breast cancer lung metastasis.
    Authors: Iriondo
    Nat Commun  2018;9(1):1994
  5. Ubiquitin-Mediated Regulation of RIPK1 Kinase Activity Independent of IKK and MK2.
    Authors: Annibaldi Et al.
    Mol Cell  2018;69:566
  6. Inflammatory but not mitogenic contexts prime synovial fibroblasts for compensatory signaling responses to p38 inhibition.
    Authors: Jones Et al.
    Sci Signal  2018;11
  7. Central Administration of 5Z-7-Oxozeaenol Protects Experimental Autoimmune Encephalomyelitis Mice by Inhibiting Microglia Activation.
    Authors: Lu Et al.
    Front Pharmacol  2017;8:789
  8. 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
  9. MK2 Phosphorylates RIPK1 to Prevent TNF-Induced Cell Death.
    Authors: Jaco Et al.
    Mol Cell  2017;66:698
  10. 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
  11. 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
  12. Profiling drugs for rheumatoid arthritis that inhibit synovial fibroblast activation.
    Authors: Jones Et al.
    Nat Chem Biol  2017;13:38
  13. p38 (Mapk14/11) occupies a regulatory node governing entry into primitive endoderm differentiation during preimplantation mouse embryo development.
    Authors: Thamodaran
    Open Biol  2016;6
  14. Identification of therapeutic targets applicable to clinical strategies in ovarian cancer.
    Authors: Kim Et al.
    BMC Cancer  2016;16:678
  15. 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
  16. 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
  17. 5Z-7-Oxozeanol Inhibits the Effects of TGFβ1 on Human Gingival Fibroblasts.
    Authors: Kuk Et al.
    PLoS One  2015;10:e0123689
  18. 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
  19. 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
  20. 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
  21. 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
  22. Protection from cerebral ischemia by inhibition of TGFβ-activated kinase.
    Authors: White Et al.
    Exp Neurol  2012;237:238
  23. The E3 ligase Itch and deubiquitinase Cyld act together to regulate Tak1 and inflammation.
    Authors: Ahmed Et al.
    Nat Immunol  2011;12:1176
  24. 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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Works for kinase assay, easy storage
By Scott Scarneo on 02/06/2019
Species: Human

Works great for kinase assay. This was tested in TAK1 in vitro kinase assay.


Great inhibitor for TAK1 signaling
By Anonymous on 12/04/2017
Species: Mouse

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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