(5Z)-7-Oxozeaenol A signal-specific JNK/p38 pathway and TAK 1 inhibitor

(5Z)-7-Oxozeaenol (CAS 253863-19-3)

(5Z)-7-Oxozeaenol | CAS 253863-19-3 is rated 5.0 out of 5 by 1.
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Synonym: C292; L 783278
Application: A signal-specific JNK/p38 pathway and TAK 1 inhibitor
CAS Number: 253863-19-3
Purity: >99%
Molecular Weight: 362.37
Molecular Formula: C19H22O7
Supplemental Information: This is classified as a Dangerous Good for transport and may be subject to additional shipping charges.
* Refer to Certificate of Analysis for lot specific data (including water content).
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Antibiotic LL Z1640-2 is a signal-specific inhibitor of the JNK/p38 pathways that has been shown to inhibit anisomycin-induced but not TNF-induced JNK/p38 activation. Shown to inhibit HgCl2 and CdCl2 MAPKs activation, while not affecting total protein level, in CCRF-CEM and NIH3T3 cells, respectively. Like other members of the resorcylic acid lactone (RAL) family, LL-Z1640-2 targets the ATP-binding pocket of kinases. Unlike other RALs, irreversibly inhibits TAK1. This cis-enone resorcylic acid lactone was first reported in 1978 and later rediscovered as an irreversible and highly selective TAK1 inhibitor. TAK1 is a MAPKKK involved in the p38 signalling cascade for pro-inflammation signals such as cytokines.


References

1. Takehana, K., et al. 1999. Biochem. Biophys. Res. Commun. 257: 19-23. PMID: 10092503
2. Matsuoka, M., et al. 2000. Eur. J. Pharmacol. 409: 155-158. PMID: 11104828
3. Wispriyono, B., et al. 2002. Environ. Health Perspect. 110: 139-143. PMID: 11836141
4. English, J.M., et al. 2002. Trends Pharmacol. Sci. 23: 40-45. PMID: 11804650
5. Sugisawa, N., et al. 2004. Toxicol. Appl. Pharmacol. 196: 206-214. PMID: 15081267
6. Murayama, T., et al. 2006. Transplantation. 81: 1325-1330. PMID: 16699462
7. Winssinger, N., et al. 2007. Chem. Commun. 22-26. PMID: 17279252
8. Gaestel, M., et al. 2007. Curr. Med. Chem. 14: 2214-2234. PMID: 17896971

Physical State :
Solid
Derived From :
Curvularia sp. MST-FP2097
Solubility :
Soluble in ethanol (10 mM), methanol, DMF, DMSO (25 mM), acetone, ethyl acetate, and water (limited solubility ). Insoluble in n-hexane.
Storage :
Store at -20° C
Boiling Point :
666.81° C at 760 mmHg (Predicted)
Density :
1.27 g/cm3 (Predicted)
Refractive Index :
n20D 1.56 (Predicted)
IC50 :
MAPKKK TAK1: IC50 = 8 nM; MEK1: IC50 = 411 nM; MEKK1: IC50 = ≥268 nM; ASK1: IC50 = ≥268 nM; MEKK4: IC50 = ≥268 nM; ERK2: IC50 = 80 nM; IL-1-induced activation of NF-κB: IC50 = 83 nM
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
Transport :
UN 2811, Class 6.1, Packing group III
PubChem CID :
9799061
MDL Number :
MFCD12912700
SMILES :
C[C@H]1C/C=C/C(=O)[C@H]([C@H](C/C=C/C2=CC(=CC(=C2C(=O)O1)O)OC)O)O

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(5Z)-7-Oxozeaenol  Product Citations

See how others have used (5Z)-7-Oxozeaenol. Click on the entry to view the PubMed entry .

Citations 1 to 4 of 4 total

PMID: # 27486461  2016. Frontiers in immunology. 7: 277.

PMID: # 26673139  Galindo-Villegas, J. et al. 2016. J. Immunol. 196: 738-49.

PMID: # 23333803  Menden, H. et al. 2013. Am. J. Physiol. Lung Cell Mol. Physiol. 304: L445-55.

PMID: # 11258483  Matsuda, S. et al. 2000. EMBO Rep. 1: 428-434.

Citations 1 to 4 of 4 total
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Rated 5 out of 5 by from Matsuda et al Matsuda et al. (PubMed ID 11258483) used Antibiotic LL Z1640-2 (LL-Z) to block T-cell activation by inhibiting JNK and p38 pathways. -SCBT Publication Review
Date published: 2015-02-07
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