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(5Z)-7-Oxozeaenol

Catalog No.
B7443
TAK1 mitogen-activated protein kinase kinase kinase (MAPKKK) inhibitor
Grouped product items
SizePriceStock Qty
1mg
$67.00
Ship with 5-10 days
5mg
$299.00
Ship with 5-10 days

Tel: +1-832-696-8203

Email: [email protected]

Worldwide Distributors

Background

(5Z)-7-Oxozeaenol is a natural resorcylic lactone derived from fungi that selectively inhibits purified TAK-1 (IC50 = 8.1 nM) without significantly affecting the kinase activities of other MAPKKK family members. 

In cells, (5Z)-7-Oxozeaenol is reported to irreversibly block IL-1-induced activation of TAK-1, NF-κB, and JNK/p38 with IC50 values of 65-83 nM. 

(5Z)-7-Oxozeaenol has also been shown to inhibit IL-1-induced COX-2 production in cells and to relieve ear swelling induced by picryl chloride in a mouse model of COX-2-mediated inflammation. 

Reference:

[1]. Ninomiya-Tsuji J, Kajino T, Ono K, et al. A resorcylic acid lactone, 5Z-7-oxozeaenol, prevents inflammation by inhibiting the catalytic activity of TAK1 MAPK kinase kinase. J. Biol. Chem, 2003, 278(20): 18485-18490.

Product Citation

Chemical Properties

Physical AppearanceWhite solid
StorageDesiccate at -20°C
M.Wt362.37
Cas No.253863-19-3
FormulaC19H22O7
Solubility<9.06mg/ml in DMSO;insoluble in ethanol
Chemical Name(3S,5Z,8S,9S,11E)-8,9,16-trihydroxy-14-methoxy-3-methyl-3,4,9,10-tetrahydro-1H-benzo[c][1]oxacyclotetradecine-1,7(8H)-dione
SDFDownload SDF
Canonical SMILESO[[email protected]@H](C/C=C/C(C=C1OC)=C(C(O)=C1)C(O[[email protected]@H](C)C/C=C\C2=O)=O)[[email protected]@H]2O
Shipping ConditionEvaluation sample solution: ship with blue ice. All other available sizes: ship with RT, or blue ice upon request.
General tipsFor obtaining a higher solubility, please warm the tube at 37°C and shake it in the ultrasonic bath for a while. Stock solution can be stored below -20°C for several months.

Protocol

Cell experiment:[1]

Cell lines

Mouse embryonic fibroblast cells

Reaction Conditions

500 nM (5Z)-7-oxozeaenol for 17.5 h incubation

Applications

In cell culture, (5Z)-7-oxozeaenol blocked interleukin-1-induced activation of TAK1, JNK/p38 MAPK, IκB kinases, and NF-κB, resulting in inhibition of cyclooxgenase-2 production.

Animal experiment:[1]

Animal models

Mice repeatedly sensitized by picryl chloride (PC) and subsequently challenged with PC

Dosage form

10 μl of (5Z)-7-oxozeaenol (1 mg/ml)

Painted on each ear 2 h before and 4 h after the second PC challenge (total of twice) or every hour three times before and 4 h after the second PC challenge (total of four times)

Applications

When (5Z)-7-oxozeaenol was administrated to the PC-challenged ear, ear swelling was reduced by up to 50% of that of the control ear treated with vehicle. Thus, (5Z)-7-oxozeaenol was able to prevent inflammation by inhibiting the catalytic activity of TAK1 MAPKKK.

Note

The technical data provided above is for reference only.

References:

1. Ninomiya-Tsuji J, Kajino T, Ono K, et al. A resorcylic acid lactone, 5Z-7-oxozeaenol, prevents inflammation by inhibiting the catalytic activity of TAK1 MAPK kinase kinase. Journal of Biological Chemistry, 2003, 278(20): 18485-18490.

Quality Control

Quality Control & MSDS

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Chemical structure

(5Z)-7-Oxozeaenol