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O9890

Sigma-Aldrich

5Z-7-Oxozeaenol

≥98% (HPLC), powder, TAK1 inhibitor

Sinonimo/i:

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

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About This Item

Formula empirica (notazione di Hill):
C19H22O7
Numero CAS:
253863-19-3
Peso molecolare:
362.37
Numero MDL:
MFCD12912700
Codice UNSPSC:
12352200
ID PubChem:
329818946
NACRES:
NA.77

product name

5Z-7-Oxozeaenol, ≥98% (HPLC)

Saggio

≥98% (HPLC)

Forma fisica

powder

Colore

white to off-white

Solubilità

DMSO: >10 mg/mL

Temperatura di conservazione

2-8°C

Stringa SMILE

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
NEQZWEXWOFPKOT-BYRRXHGESA-N

Applicazioni

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

Azioni biochim/fisiol

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.

Caratteristiche e vantaggi

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.

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Certificati d'analisi (COA)

Cerca il Certificati d'analisi (COA) digitando il numero di lotto/batch corrispondente. I numeri di lotto o di batch sono stampati sull'etichetta dei prodotti dopo la parola ‘Lotto’ o ‘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
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Articoli

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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