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O9890

Sigma-Aldrich

5Z-7-Oxozeaenol

≥98% (HPLC), powder, TAK1 inhibitor

Synonym(s):

C 292, F 152, FR148083, L 783279, LL-Z1640-2

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About This Item

Empirical Formula (Hill Notation):
C19H22O7
CAS Number:
253863-19-3
Molecular Weight:
362.37
MDL number:
MFCD12912700
UNSPSC Code:
12352200
PubChem Substance ID:
329818946
NACRES:
NA.77

product name

5Z-7-Oxozeaenol, ≥98% (HPLC)

Assay

≥98% (HPLC)

form

powder

color

white to off-white

solubility

DMSO: >10 mg/mL

storage temp.

2-8°C

SMILES string

COc1cc(O)c2C(=O)O[C@@H](C)CC=CC(=O)[C@@H](O)[C@@H](O)C\C=C\c2c1

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/b6-4+,7-3-/t11-,15-,18+/m0/s1

InChI key

NEQZWEXWOFPKOT-BYRRXHGESA-N

Application

5Z-7-Oxozeaenol has been used:
  • as transforming growth factor β-activated kinase 1 (TAK1) inhibitor to treat human colon cancer cells
  • as TAK1-specific inhibitor to provide intraperitoneal injection to mice for aortic banding
  • as TAK1 inhibitor to treat cells for luciferase reporter assay
  • to test growth and differentiation factor 2 (GDF2)-mediated anoikis

Biochem/physiol Actions

5Z-7-oxozeaenol is a potent ATP-competitive irreversible inhibitor of ERK2 (IC50 = 80 nM), TAK1 (MEKK7), MKK7, and MEK1, which all contain a common cysteine residue in the ATP-binding site. 5Z-7-oxozeaenol has no activity against other MAP kinases. 5Z-7-oxozeaenol is also anti-inflammatory.
The anti-inflammatory effects of 5Z-7-oxozeaenol may affect cardiac hypertrophy.

Features and Benefits

This compound is a featured product for Kinase Phosphatase Biology research. Click here to discover more featured Kinase Phosphatase Biology products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the MAPKKKs and MAPKs pages of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Cytosolic Internalization of Anti-DNA Antibodies by Human Monocytes Induces Production of Pro-Inflammatory Cytokines Independently of the Tripartite Motif-Containing 21 (TRIM21)-Mediated Pathway
Park H, et al.
Frontiers in Immunology, 9 (2018)
Epigenetic regulation of GDF2 suppresses anoikis in ovarian and breast epithelia
Varadaraj A, et al.
Neoplasia, 17(11), 826-838 (2015)
Disruption of thioredoxin metabolism enhances the toxicity of transforming growth factor beta-activated kinase 1 (TAK1) inhibition in KRAS-mutated colon cancer cells
Hrabe JE, et al.
Redox Biology, 5, 319-327 (2015)
Dual-specificity phosphatase 14 protects the heart from aortic banding-induced cardiac hypertrophy and dysfunction through inactivation of TAK1-P38MAPK/-JNK1/2 signaling pathway
Li CY, et al.
Basic Research in Cardiology, 111(2), 19-19 (2016)
Te-Chia Wu et al.
Cancer research, 78(18), 5243-5258 (2018-07-18)
Inflammation affects tumor immune surveillance and resistance to therapy. Here, we show that production of IL1β in primary breast cancer tumors is linked with advanced disease and originates from tumor-infiltrating CD11c+ myeloid cells. IL1β production is triggered by cancer cell
View All Related Papers

Articles

MAPKKKs

The extracellular signal regulated kinase (ERK1 and ERK2) pathways are activated by mitogens and play an important role in controlling cell growth and differentiation.

MAPKs

The mitogen-activated protein kinase (MAPK) family consists of both stress activated (SAPK) and mitogen-activated (MAPK) protein kinases. They form a network of signal transduction cascades that mediate cellular responses to a diverse range of stimuli, including growth factors, chemical or osmotic stress, irradiation, bacterial infection and proinflammatory cytokines.

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