Molecular structure of (5Z)-7-Oxozeaenol, CAS Number: 253863-19-3
(5Z)-7-Oxozeaenol (CAS 253863-19-3)
See product citations (13)
Alternate Names:
C292; L 783278; LL Z1640-2
Application:
(5Z)-7-Oxozeaenol is a signal-specific JNK/p38 pathway and TAK 1 inhibitor
CAS Number:
253863-19-3
Purity:
≥95%
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.
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.
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SDS & Certificate of Analysis
(5Z)-7-Oxozeaenol also known as antibiotic LL Z1640-2 is a signal-specific inhibitor of the JNK/p38 pathways that may act 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,(5Z)-7-Oxozeaenol 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.
(5Z)-7-Oxozeaenol (CAS 253863-19-3) References
- A radicicol-related macrocyclic nonaketide compound, antibiotic LL-Z1640-2, inhibits the JNK/p38 pathways in signal-specific manner. | Takehana, K., et al. 1999. Biochem Biophys Res Commun. 257: 19-23. PMID: 10092503
- Inhibition of HgCl2-induced mitogen-activated protein kinase activation by LL-Z1640-2 in CCRF-CEM cells. | Matsuoka, M., et al. 2000. Eur J Pharmacol. 409: 155-8. PMID: 11104828
- Pharmacological inhibitors of MAPK pathways. | English, JM. and Cobb, MH. 2002. Trends Pharmacol Sci. 23: 40-5. PMID: 11804650
- Effects of pentachlorophenol and tetrachlorohydroquinone on mitogen-activated protein kinase pathways in Jurkat T cells. | Wispriyono, B., et al. 2002. Environ Health Perspect. 110: 139-43. PMID: 11836141
- Suppression of cadmium-induced JNK/p38 activation and HSP70 family gene expression by LL-Z1640-2 in NIH3T3 cells. | Sugisawa, N., et al. 2004. Toxicol Appl Pharmacol. 196: 206-14. PMID: 15081267
- JNK (c-Jun NH2 terminal kinase) and p38 during ischemia reperfusion injury in the small intestine. | Murayama, T., et al. 2006. Transplantation. 81: 1325-30. PMID: 16699462
- Chemistry and biology of resorcylic acid lactones. | Winssinger, N. and Barluenga, S. 2007. Chem Commun (Camb). 22-36. PMID: 17279252
- Protein kinases as small molecule inhibitor targets in inflammation. | Gaestel, M., et al. 2007. Curr Med Chem. 14: 2214-34. PMID: 17896971
- Effects of (5Z)-7-oxozeaenol on the oxidative pathway of cancer cells. | Acuña, UM., et al. 2012. Anticancer Res. 32: 2665-71. PMID: 22753724
- 5Z-7-Oxozeaenol covalently binds to MAP2K7 at Cys218 in an unprecedented manner. | Sogabe, Y., et al. 2015. Bioorg Med Chem Lett. 25: 593-6. PMID: 25529738
- Enhancement of hyperthermia-induced apoptosis by 5Z-7-oxozeaenol, a TAK1 inhibitor, in A549 cells. | Li, P., et al. 2016. Cell Stress Chaperones. 21: 873-81. PMID: 27448221
- Central Administration of 5Z-7-Oxozeaenol Protects Experimental Autoimmune Encephalomyelitis Mice by Inhibiting Microglia Activation. | Lu, L., et al. 2017. Front Pharmacol. 8: 789. PMID: 29163172
- (5Z)-7-Oxozeaenol: A novel and potent resorcylic acid lactone kinase inhibitor with a cis-enone Michael acceptor. | Ellestad, GA. 2019. Chirality. 31: 110-117. PMID: 30565749
Inhibitor of:
C-TAK1L, EG623186, MEKK 15, OXSR1, p38, Ser/Thr Protein Kinase, TAB, Tak1, Tak1L, and TRAF2.Activator of:
group VI iPLA2, LTβR, RIP, and RIP3.Ordering Information
| Product Name | Catalog # | UNIT | Price | Qty | FAVORITES | |
(5Z)-7-Oxozeaenol, 1 mg | sc-202055 | 1 mg | $157.00 | |||
(5Z)-7-Oxozeaenol, 5 mg | sc-202055A | 5 mg | $646.00 |