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499610

Sigma-Aldrich

(5Z)-7-Oxozeaenol, Curvularia sp.

(5Z)-7-Oxozeaenol, CAS 66018-38-0, is a cell-permeable, highly potent, selective, irreversible, and ATP-competitive inhibitor of MAPKKK TAK1 activity (IC₅₀ = 8 nM).

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Synonym(s):
(5Z)-7-Oxozeaenol, Curvularia sp., TAK1 Inhibitor
Empirical Formula (Hill Notation):
C19H22O7
CAS Number:
Molecular Weight:
362.37
NACRES:
NA.77

Quality Level

assay

≥97% (HPLC)

form

solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
protect from light

color

white

solubility

DMSO: 10 mg/mL
ethanol: 5 mg/mL

shipped in

wet ice

storage temp.

−20°C

InChI

1S/C19H22O7/c1-11-5-3-7-14(20)18(23)15(21)8-4-6-12-9-13(25-2)10-16(22)17(12)19(24)26-11/h3-4,6-7,9-11,15,18,21-23H,5,8H2,1-2H3

InChI key

NEQZWEXWOFPKOT-UHFFFAOYSA-N

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This Item
677181580555495604
vibrant-m

499610

(5Z)-7-Oxozeaenol, Curvularia sp.

vibrant-m

580555

Paclitaxel, Taxus sp.

vibrant-m

495604

Okadaic Acid, Prorocentrum sp.

form

solid

form

solid

form

solid

form

solid (glassy)

assay

≥97% (HPLC)

assay

≥98% (TLC)

assay

≥97% (HPLC)

assay

≥95% (HPLC)

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

shipped in

wet ice

shipped in

ambient

shipped in

ambient

shipped in

ambient

storage condition

OK to freeze, protect from light

storage condition

OK to freeze

storage condition

OK to freeze, desiccated, protect from light

storage condition

OK to freeze, protect from light

General description

A naturally isolated cell-permeable fungal resorcylic lactone that acts as a selective and highly potent inhibitor against the MAPKKK TAK1 activity (IC50 = 8 nM) in an ATP-competitive and irreversible manner, while inhibiting MEK1 (IC50 = 411 nM) and three other MAPKKKs (IC50 ≥268 nM against MEKK1, ASK1, and MEKK4) only at much higher concentrations. Shown to inhibit IL-1-induced/TAK1-mediated, but not H2O2-induced/TAK1-independent, JNK and p38 phosphorylation in 293 cells. (5Z)-Zeaenol, Curvularia sp. (Cat. No. 499609) may serve as a negative control.
A naturally isolated cell-permeable fungal resorcylic lactone that acts as a selective and highly potent inhibitor against the MAPKKK TAK1 activity (IC50 = 8 nM) in an ATP-competitive and irreversible manner, while inhibiting MEK1 (IC50 = 411 nM) and three other MAPKKKs (IC50 ≥268 nM against MEKK1, ASK1, and MEKK4) only at much higher concentrations. Shown to inhibit IL-1-induced/TAK1-mediated, but not H2O2-induced/TAK1-independent, JNK and p38 phosphorylation in 293 cells. (5Z)-Zeaenol, Curvularia sp.(Cat. No. 499609) may serve as a negative control.

Warning

Toxicity: Standard Handling (A)

Reconstitution

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 6 months at -20°C.

Other Notes

Windheim, M., et al. 2007. Biochem. J.404, 179.
Choo, M.K., et al. 2006. Mol. Cancer Ther.5, 2970.
Safwat, N., et al. 2005. Endocrinology146, 4814.
Ninomiya-Tsuji, J., et al. 2003. J. Biol. Chem.278, 18485.
Rawlins, P., et al. 1999. Int. J. Immunopharmacol.21, 799.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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Christoph Lammel et al.
Biomolecules, 10(9) (2020-08-23)
Twenty natural remedies traditionally used against different inflammatory diseases were probed for their potential to suppress the expression of the inflammatory markers E-selectin and VCAM-1 in a model system of IL-1 stimulated human umbilical vein endothelial cells (HUVEC). One third

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