Home / Other Kinase Inhibitors / (5Z)-7-Oxozeaenol

(5Z)-7-Oxozeaenol

Catalog #: 3604
40 Citations Datasheet / COA / SDS
Catalog # Availability Size / Price Qty
3604/1
(5Z)-7-Oxozeaenol | CAS No. 253863-19-3 | Other Kinase Inhibitors
1 Image
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 (40)
Reviews
Biological Activity Technical Data Background Product Datasheets Calculators

Biological Activity

(5Z)-7-Oxozeaenol is a 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
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.

Background References

  1. p38 (Mapk14/11) occupies a regulatory node governing entry into primitive endoderm differentiation during preimplantation mouse embryo development

    Open Biol, 2016;6(9):.
  2. Apoptosis-associated speck-like protein containing a CARD forms specks but does not activate caspase-1 in the absence of NLRP3 during macrophage swelling.
    Compan V, Martin-Sanchez F, Baroja-Mazo A, Lopez-Castejon G, Gomez A, Verkhratsky A, Brough D, Pelegrin P
    J Immunol, 2015;194(3):1261-73.
  3. TLR signalling in human antigen-presenting cells regulates MR1-dependent activation of MAIT cells
    JE Ussher, B van Wilgen, RF Hannaway, K Ruustal, P Phalora, A Kurioka, TH Hansen, CB Willberg, RE Phillips, P Klenerman
    Eur J Immunol, 2016;0(0):.
  4. Kaposi's sarcoma associated herpesvirus encoded viral FLICE inhibitory protein K13 activates NF-κB pathway independent of TRAF6, TAK1 and LUBAC.
    Matta H, Gopalakrishnan R, Graham C, Tolani B, Khanna A, Yi H, Suo Y, Chaudhary PM
    PLoS ONE, 2012;7(5):e36601.
  5. 5Z-7-Oxozeanol Inhibits the Effects of TGFbeta1 on Human Gingival Fibroblasts.
    Kuk H, Hutchenreuther J, Murphy-Marshman H, Carter D, Leask A
    PLoS ONE, 2015;10(4):e0123689.
  6. Myostatin regulates energy homeostasis in the heart and prevents heart failure.
    Biesemann N, Mendler L, Wietelmann A, Hermann S, Schafers M, Kruger M, Boettger T, Borchardt T, Braun T
    Circ Res, 2014;115(2):296-310.
  7. A key role for the endothelium in NOD1 mediated vascular inflammation: comparison to TLR4 responses.
    Gatheral T, Reed D, Moreno L, Gough P, Votta B, Sehon C, Rickard D, Bertin J, Lim E, Nicholson A, Mitchell J
    PLoS ONE, 2012;7(8):e42386.
  8. 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
  9. 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
  10. Molecular mechanisms involved in the regulation of cytokine production by muramyl dipeptide.
    Windheim et al.
    Biochem.J., 2007;404:179

Product Datasheets

COA view current batch
Or select another batch:
View Batch
SDS
Reconstitution Calculator
Molarity Calculator

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.

=
÷

Molarity Calculator

=
x
x
g/mol

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

Citations for (5Z)-7-Oxozeaenol

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

40 Citations: Showing 1 - 10

  1. Caspase-8-driven apoptotic and pyroptotic crosstalk causes cell death and IL-1β release in X-linked inhibitor of apoptosis (XIAP) deficiency.
    Authors: Kate E Et al.
    EMBO J  2023;42:e110468
  2. Induction of pro-inflammatory genes by fibronectin DAMPs in three fibroblast cell lines: Role of TAK1 and MAP kinases.
    Authors: Anthony Et al.
    PLoS One  2023;18:e0286390
  3. Pharmacologic Targeting of TFIIH Suppresses KRAS-Mutant Pancreatic Ductal Adenocarcinoma and Synergizes with TRAIL.
    Authors: Christopher J Et al.
    Cancer Res  2022;82:3375-3393
  4. TAK1 protein kinase activity is required for TLR signalling and cytokine production in myeloid cells.
    Authors: Tsvetana Et al.
    Biochem J  2022;479:1891-1907
  5. Topical application of TAK1 inhibitor encapsulated by gelatin particle alleviates corneal neovascularization.
    Authors: Guei-Sheung Et al.
    Theranostics  2022;12:657-674
  6. TAK1 inhibition increases proliferation and differentiation of chick retinal cells.
    Authors: Teri L Et al.
    Front Cell Dev Biol  2022;10:698233
  7. Cardiac Tissue Factor Regulates Inflammation, Hypertrophy, and Heart Failure in Mouse Model of Type 1 Diabetes.
    Authors: Nigel Et al.
    Diabetes  2021;70:2131-2146
  8. Inhibition of the MAP2K7-JNK pathway with 5Z-7-oxozeaenol induces apoptosis in T-cell acute lymphoblastic leukemia.
    Authors: Ye Et al.
    Oncotarget  2021;12:1787-1801
  9. CD137 Signaling Regulates Acute Colitis via RALDH2-Expressing CD11b-CD103+ DCs.
    Authors: Seungwoon Et al.
    Cell Rep  2020;30:4124-4136.e5
  10. Tristetraprolin regulates necroptosis during tonic Toll-like receptor 4 (TLR4) signaling in murine macrophages.
    Authors: Deborah J Et al.
    J Biol Chem  2020;295:4661-4672
  11. FoxO1 is a crucial mediator of TGF-β/TAK1 signaling and protects against osteoarthritis by maintaining articular cartilage homeostasis.
    Authors: Jie Et al.
    Proc Natl Acad Sci U S A  2020;117:30488-30497
  12. TAK1 signaling regulates p53 through a mechanism involving ribosomal stress.
    Authors: Michelle Et al.
    Sci Rep  2020;10:2517
  13. Platelet-derived β2M regulates monocyte inflammatory responses.
    Authors: Hilt Et al.
    JCI Insight  2019;4
  14. 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
  15. 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
  16. TAK1 converts Sequestosome 1/p62 from an autophagy receptor to a signaling platform.
    Authors: Bhaskar Et al.
    EMBO Rep  2019;20:e46238
  17. TAK1 mediates microenvironment-triggered autocrine signals and promotes triple-negative breast cancer lung metastasis.
    Authors: Iriondo
    Nat Commun  2018;9(1):1994
  18. Ubiquitin-Mediated Regulation of RIPK1 Kinase Activity Independent of IKK and MK2.
    Authors: Annibaldi Et al.
    Mol Cell  2018;69:566
  19. Inflammatory but not mitogenic contexts prime synovial fibroblasts for compensatory signaling responses to p38 inhibition.
    Authors: Jones Et al.
    Sci Signal  2018;11
  20. Central Administration of 5Z-7-Oxozeaenol Protects Experimental Autoimmune Encephalomyelitis Mice by Inhibiting Microglia Activation.
    Authors: Lu Et al.
    Front Pharmacol  2017;8:789
  21. 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
  22. MK2 Phosphorylates RIPK1 to Prevent TNF-Induced Cell Death.
    Authors: Jaco Et al.
    Mol Cell  2017;66:698
  23. 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
  24. 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
  25. Regulatory role of tumor necrosis factor receptor-associated factor 6 in breast cancer by activating the protein kinase B/glycogen synthase kinase 3β signaling pathway.
    Authors: Dandan Et al.
    Mol Med Rep  2017;16:2269-2273
  26. Profiling drugs for rheumatoid arthritis that inhibit synovial fibroblast activation.
    Authors: Jones Et al.
    Nat Chem Biol  2017;13:38
  27. p38 (Mapk14/11) occupies a regulatory node governing entry into primitive endoderm differentiation during preimplantation mouse embryo development.
    Authors: Thamodaran
    Open Biol  2016;6
  28. Identification of therapeutic targets applicable to clinical strategies in ovarian cancer.
    Authors: Kim Et al.
    BMC Cancer  2016;16:678
  29. 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
  30. 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
  31. Inhibition of glycogen synthase kinase-3β enhances cognitive recovery after stroke: the role of TAK1.
    Authors: Sharon E Et al.
    Learn Mem  2015;22:336-43
  32. 5Z-7-Oxozeanol Inhibits the Effects of TGFβ1 on Human Gingival Fibroblasts.
    Authors: Kuk Et al.
    PLoS One  2015;10:e0123689
  33. 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
  34. 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
  35. 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
  36. Inhibition of TAK1 and/or JAK can rescue impaired chondrogenic differentiation of human mesenchymal stem cells in osteoarthritis-like conditions.
    Authors: Wim B Et al.
    Tissue Eng Part A  2014;20:2243-52
  37. 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
  38. Protection from cerebral ischemia by inhibition of TGFβ-activated kinase.
    Authors: White Et al.
    Exp Neurol  2012;237:238
  39. The E3 ligase Itch and deubiquitinase Cyld act together to regulate Tak1 and inflammation.
    Authors: Ahmed Et al.
    Nat Immunol  2011;12:1176
  40. 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

FAQs

No product specific FAQs exist for this product, however you may

View all Small Molecule FAQs

Reviews for (5Z)-7-Oxozeaenol

There are currently no reviews for this product. Be the first to review (5Z)-7-Oxozeaenol and earn rewards!

Have you used (5Z)-7-Oxozeaenol?

Submit a review and receive an Amazon gift card.

$25/€18/£15/$25CAN/¥75 Yuan/¥2500 Yen for a review with an image

$10/€7/£6/$10 CAD/¥70 Yuan/¥1110 Yen for a review without an image

Submit a Review
Tocris Bioscience is the leading supplier of novel and exclusive tools for life science research with over 30 years' experience in the industry. Tocris is a Bio-Techne brand.