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Submit Review(5Z)-7-Oxozeaenol
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)
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 |
| InChI Key | NEQZWEXWOFPKOT-ULSULSEOSA-N |
| 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 | |
|---|---|---|---|
| Solubility | |||
| 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.
| 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
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:
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
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
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
Hilt et al (2019) Platelet-derived β2M regulates monocyte inflammatory responses. JCI Insight 4 PMID: 30702442
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
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
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
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
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
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
White et al (2012) Protection from cerebral ischemia by inhibition of TGFβ-activated kinase. Exp Neurol 237 238 PMID: 22683931
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
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
Kim et al (2016) Identification of therapeutic targets applicable to clinical strategies in ovarian cancer. BMC Cancer 16 678 PMID: 27558154
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
Iriondo (2018) TAK1 mediates microenvironment-triggered autocrine signals and promotes triple-negative breast cancer lung metastasis. Nat Commun 9 1994 PMID: 29777109
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
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
Bhaskar et al (2019) TAK1 converts Sequestosome 1/p62 from an autophagy receptor to a signaling platform. EMBO Rep 20 e46238 PMID: 31347268
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
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
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
Ahmed et al (2011) The E3 ligase Itch and deubiquitinase Cyld act together to regulate Tak1 and inflammation. Nat Immunol 12 1176 PMID: 22057290
Do you know of a great paper that uses (5Z)-7-Oxozeaenol from Tocris? Please let us know.
Reviews for (5Z)-7-Oxozeaenol
Average Rating: 5 (Based on 2 Reviews.)
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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.
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.
