(5Z)-7-Oxozeaenol

Name: (5 Z )-7-Oxozeaenol
Brand: Tocris Bioscience
SKU: 3604

Tocris Bioscience, part of Bio-Techne | Catalog # 3604

(2)

Citations (108)

COA / SDS

Potent and selective TAK1 MAPKKK inhibitor

Key Product Details

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%
Molecular Weight:	362.37 kDa

View Full Technical Details for (5Z)-7-Oxozeaenol

Technical Data
Citations / 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 kDa
Formula	C₁₉H₂₂O₇
Storage	Desiccate at -20°C
Purity	≥98%
CAS Number	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.

Solubility for (5Z)-7-Oxozeaenol

Solubility

Soluble Soluble to 25 mM in DMSO

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.

Mass

Concentration

Volume

M. Wt*

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).

Dilution Calculator

Calculate the dilution required to prepare a stock solution.

Concentration 1 (C1)

Volume 1 (V1)

Concentration 2 (C2)

Volume 2 (V2)

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.

Volume (to add to vial)

Mass (in vial)

Desired Reconstitution Concentration

References for (5Z)-7-Oxozeaenol

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

Gatheral T, Reed D, Moreno L, Gough P, Votta B, Sehon C, Rickard D, Bertin J, Lim E, Nicholson A, Mitchell J A key role for the endothelium in NOD1 mediated vascular inflammation: comparison to TLR4 responses. PLoS ONE, 2012;7(8):e42386. 2012 PMID: 22870324
Biesemann N, Mendler L, Wietelmann A, Hermann S, Schafers M, Kruger M, Boettger T, Borchardt T, Braun T Myostatin regulates energy homeostasis in the heart and prevents heart failure. Circ Res, 2014;115(2):296-310. 2014 PMID: 24807786
Kuk H, Hutchenreuther J, Murphy-Marshman H, Carter D, Leask A 5Z-7-Oxozeanol Inhibits the Effects of TGFbeta1 on Human Gingival Fibroblasts. PLoS ONE, 2015;10(4):e0123689. 2015 PMID: 25927238
Matta H, Gopalakrishnan R, Graham C, Tolani B, Khanna A, Yi H, Suo Y, Chaudhary PM Kaposi's sarcoma associated herpesvirus encoded viral FLICE inhibitory protein K13 activates NF-ÃŽÂºB pathway independent of TRAF6, TAK1 and LUBAC. PLoS ONE, 2012;7(5):e36601. 2012 PMID: 22590573
JE Ussher, B van Wilgen, RF Hannaway, K Ruustal, P Phalora, A Kurioka, TH Hansen, CB Willberg, RE Phillips, P Klenerman TLR signalling in human antigen-presenting cells regulates MR1-dependent activation of MAIT cells Eur J Immunol, 2016;0(0):. 2016 PMID: 27105778
Compan V, Martin-Sanchez F, Baroja-Mazo A, Lopez-Castejon G, Gomez A, Verkhratsky A, Brough D, Pelegrin P Apoptosis-associated speck-like protein containing a CARD forms specks but does not activate caspase-1 in the absence of NLRP3 during macrophage swelling. J Immunol, 2015;194(3):1261-73. 2015 PMID: 25552542
Ninomiya-Tsuji et al. A resorcyclic acid lactone, 5Z-7-Oxozeaenol, prevents inflammation by inhibiting the catalytic activity of TAK1 MAPK kinase kinase. J.Biol.Chem., 2003;278:18485 PMID: 12624112
Choo et al. Blockade of transforming growth factor-β-activated kinase 1 activity enhances TRAIL-induced apoptosis through activation of a caspase cascade. Mol.Cancer Ther., 2006;5:2970 PMID: 17172402
Windheim et al. Molecular mechanisms involved in the regulation of cytokine production by muramyl dipeptide. Biochem.J., 2007;404:179 PMID: 17348859