Pricing Availability   Qty
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% (HPLC)
Citations (40)
Reviews (2)

Biological Activity for (5Z)-7-Oxozeaenol

(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 for (5Z)-7-Oxozeaenol

M. Wt 362.37
Formula C19H22O7
Storage Desiccate at -20°C
Purity ≥98% (HPLC)
CAS Number 253863-19-3
PubChem ID 9799061
Smiles O=C/2[C@@H](O)[C@@H](O)C/C=C/C1=CC(OC)=CC(O)=C1C(O[C@@H](C)C\C=C2)=O

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.

Solubility Data for (5Z)-7-Oxozeaenol

Solvent Max Conc. mg/mL Max Conc. mM
DMSO 9.06 25

Preparing Stock Solutions for (5Z)-7-Oxozeaenol

The following data is based on the product molecular weight 362.37. Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
0.25 mM 11.04 mL 55.19 mL 110.38 mL
1.25 mM 2.21 mL 11.04 mL 22.08 mL
2.5 mM 1.1 mL 5.52 mL 11.04 mL
12.5 mM 0.22 mL 1.1 mL 2.21 mL

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Product Datasheets for (5Z)-7-Oxozeaenol

Certificate of Analysis / Product Datasheet
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References for (5Z)-7-Oxozeaenol

References are publications that support the biological activity of the product.

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

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

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

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

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Keywords: (5Z)-7-Oxozeaenol, (5Z)-7-Oxozeaenol supplier, Potent, selective, TAK1, MAPKKK, inhibitors, inhibits, Kinases, Other, 3604, Tocris Bioscience

40 Citations for (5Z)-7-Oxozeaenol

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

Iriondo (2018) TAK1 mediates microenvironment-triggered autocrine signals and promotes triple-negative breast cancer lung metastasis. Nat Commun 9 1994 PMID: 29777109

Dandan et al (2017) 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. Mol Med Rep 16 2269-2273 PMID: 28627683

Michelle et al (2020) TAK1 signaling regulates p53 through a mechanism involving ribosomal stress. Sci Rep 10 2517 PMID: 32054925

Seungwoon et al (2020) CD137 Signaling Regulates Acute Colitis via RALDH2-Expressing CD11b-CD103+ DCs. Cell Rep 30 4124-4136.e5 PMID: 32209473

Deborah J et al (2020) Tristetraprolin regulates necroptosis during tonic Toll-like receptor 4 (TLR4) signaling in murine macrophages. J Biol Chem 295 4661-4672 PMID: 32094226

Jie et al (2020) FoxO1 is a crucial mediator of TGF-β/TAK1 signaling and protects against osteoarthritis by maintaining articular cartilage homeostasis. Proc Natl Acad Sci U S A 117 30488-30497 PMID: 33199631

Kim et al (2016) Identification of therapeutic targets applicable to clinical strategies in ovarian cancer. BMC Cancer 16 678 PMID: 27558154

Sharon E et al (2015) Inhibition of glycogen synthase kinase-3β enhances cognitive recovery after stroke: the role of TAK1. Learn Mem 22 336-43 PMID: 26077686

Kate E et al (2023) Caspase-8-driven apoptotic and pyroptotic crosstalk causes cell death and IL-1β release in X-linked inhibitor of apoptosis (XIAP) deficiency. EMBO J 42 e110468 PMID: 36647737

Anthony et al (2023) Induction of pro-inflammatory genes by fibronectin DAMPs in three fibroblast cell lines: Role of TAK1 and MAP kinases. PLoS One 18 e0286390 PMID: 37228128

Annibaldi et al (2018) Ubiquitin-Mediated Regulation of RIPK1 Kinase Activity Independent of IKK and MK2. Mol Cell 69 566 PMID: 29452637

Jones et al (2018) Inflammatory but not mitogenic contexts prime synovial fibroblasts for compensatory signaling responses to p38 inhibition. Sci Signal 11 PMID: 29511118

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

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

Fleskens et al (2019) Nemo-like Kinase Drives Foxp3 Stability and Is Critical for Maintenance of Immune Tolerance by Regulatory T Cells. Cell Rep 26 3600 PMID: 30917315

Lu et al (2017) Central Administration of 5Z-7-Oxozeaenol Protects Experimental Autoimmune Encephalomyelitis Mice by Inhibiting Microglia Activation. Front Pharmacol 8 789 PMID: 29163172

Thamodaran (2016) p38 (Mapk14/11) occupies a regulatory node governing entry into primitive endoderm differentiation during preimplantation mouse embryo development. Open Biol 6 PMID: 27605380

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

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

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

Lionarons et al (2019) RAC1P29S Induces a Mesenchymal Phenotypic Switch via Serum Response Factor to Promote Melanoma Development and Therapy Resistance. Cancer Cell 36 68 PMID: 31257073

Hilt et al (2019) Platelet-derived β2M regulates monocyte inflammatory responses. JCI Insight 4 PMID: 30702442

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 19 112 PMID: 28569204

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

Christopher J et al (2022) Pharmacologic Targeting of TFIIH Suppresses KRAS-Mutant Pancreatic Ductal Adenocarcinoma and Synergizes with TRAIL. Cancer Res 82 3375-3393 PMID: 35819261

Tsvetana et al (2022) TAK1 protein kinase activity is required for TLR signalling and cytokine production in myeloid cells. Biochem J 479 1891-1907 PMID: 36062803

Teri L et al (2022) TAK1 inhibition increases proliferation and differentiation of chick retinal cells. Front Cell Dev Biol 10 698233 PMID: 36176271

Guei-Sheung et al (2022) Topical application of TAK1 inhibitor encapsulated by gelatin particle alleviates corneal neovascularization. Theranostics 12 657-674 PMID: 34976206

Nigel et al (2021) Cardiac Tissue Factor Regulates Inflammation, Hypertrophy, and Heart Failure in Mouse Model of Type 1 Diabetes. Diabetes 70 2131-2146 PMID: 34155039

Ye et al (2021) Inhibition of the MAP2K7-JNK pathway with 5Z-7-oxozeaenol induces apoptosis in T-cell acute lymphoblastic leukemia. Oncotarget 12 1787-1801 PMID: 34504651

Ismail et al (2017) 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. Arthritis Rheumatol 69 565 PMID: 27768832

Jones et al (2017) Profiling drugs for rheumatoid arthritis that inhibit synovial fibroblast activation. Nat Chem Biol 13 38 PMID: 27820799

Jaco et al (2017) MK2 Phosphorylates RIPK1 to Prevent TNF-Induced Cell Death. Mol Cell 66 698 PMID: 28506461

Yang et al (2017) Expression and function of transforming growth factor?β?activated protein kinase 1 in gastric cancer. Mol Med Rep 16 3103 PMID: 28714004

White et al (2012) Protection from cerebral ischemia by inhibition of TGFβ-activated kinase. Exp Neurol 237 238 PMID: 22683931

Bhaskar et al (2019) TAK1 converts Sequestosome 1/p62 from an autophagy receptor to a signaling platform. EMBO Rep 20 e46238 PMID: 31347268

Wim B et al (2014) Inhibition of TAK1 and/or JAK can rescue impaired chondrogenic differentiation of human mesenchymal stem cells in osteoarthritis-like conditions. Tissue Eng Part A 20 2243-52 PMID: 24547725

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

Do you know of a great paper that uses (5Z)-7-Oxozeaenol from Tocris? Please let us know.

Reviews for (5Z)-7-Oxozeaenol

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Works for kinase assay, easy storage.
By Scott Scarneo on 02/06/2019
Assay Type: In Vitro
Species: Human

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

review image

Great inhibitor for TAK1 signaling.
By Anonymous on 12/04/2017
Assay Type: In Vitro
Species: Mouse
Cell Line/Tissue: Primary human small airway epithelial cells

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
review image