| Size | Price | Stock | Qty |
|---|---|---|---|
| 1mg |
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| Other Sizes |
Purity: ≥98%
| Targets |
5Z-7-Oxozeaenol targets multiple kinases, including TAK1 (transforming growth factor β-activated kinase 1, also known as MAP3K7), ERK2, MKK7, and MEK1. These kinases are members of the mitogen-activated protein kinase (MAPK) signaling cascades that regulate cellular responses to stress, inflammation, and growth factors. 5Z-7-Oxozeaenol is an ATP-competitive irreversible inhibitor that covalently binds to a conserved cysteine residue in the ATP-binding site of these kinases. TAK1 is a key upstream kinase that activates JNK, p38 MAPK, and NF-κB pathways in response to pro-inflammatory cytokines such as IL-1β and TNF-α. By inhibiting TAK1 and other kinases, 5Z-7-Oxozeaenol blocks multiple inflammatory signaling pathways.
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| ln Vitro |
5Z-7-Oxozeaenol exhibits strong, irreversible, and specific inhibition of TGF-β-activated kinase 1 (TAK1, IC50, 8.1 nM), while demonstrating negligible effect against MEK1 (IC50, 411 nM). By blocking TAK1 MAPK kinase kinase's catalytic activity, 5Z-7-Oxozeaenol reduces inflammation [1]. Moreover, 5Z-7-Oxozeaenol inhibits VEGF-R2 with an IC50 of 52 nM. 5Z-7-Oxozeaenol exhibits inhibitory activity with IC50 values of 110, 170, 340, 6300, and 6600 nM, respectively, against VEGF-R3, FLT3, PDGFR-β, B-RAF VE, and SRC [2]. Although 5Z-7-Oxozeaenol is a signaling-specific inhibitor rather than a direct inhibitor, it nevertheless inhibits the JNK/p38 pathway. 5Z-7-Oxozeaenol has no effect on IL-1-induced NF-kB activity in KK cells, but it reduces PMA-induced AP-1 activity in KT cells to nearly basal levels [3].
5Z-7-Oxozeaenol demonstrates potent in vitro activity against multiple kinases. It inhibits ERK2 with an IC50 of 80 nM, TAK1, MKK7, and MEK1. The compound blocks interleukin-1-induced activation of TAK1, JNK/p38 MAPK, IκB kinases, and NF-κB, resulting in inhibition of cyclooxygenase-2 (COX-2) production. This broad inhibition of inflammatory signaling pathways makes 5Z-7-Oxozeaenol a valuable tool for studying the role of these kinases in inflammation and immunity. The compound's irreversible binding mechanism ensures sustained inhibition of its target kinases. Detailed cellular activity data, including effects on downstream signaling and cytokine production, are available in the primary literature. |
| ln Vivo |
In vivo efficacy data for 5Z-7-Oxozeaenol are not extensively documented in publicly available sources. Based on its potent in vitro inhibition of TAK1 and other kinases involved in inflammatory signaling, the compound is expected to have potential utility in inflammatory disease models. TAK1 is a well-validated target for inflammatory diseases, and inhibitors of TAK1 have shown efficacy in preclinical models of arthritis, colitis, and other inflammatory conditions. 5Z-7-Oxozeaenol's ability to block IL-1-induced NF-κB activation and COX-2 production suggests that it could be effective in reducing inflammation in vivo. Further in vivo studies are needed to fully characterize the compound's therapeutic potential, including its efficacy in disease models, pharmacokinetic properties, and safety profile.
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| Enzyme Assay |
The in vitro enzyme inhibition assay for 5Z-7-Oxozeaenol measures the inhibition of kinase activities. Recombinant human kinases (TAK1, ERK2, MKK7, MEK1) are incubated with varying concentrations of 5Z-7-Oxozeaenol (typically ranging from nanomolar to micromolar) in the presence of ATP and a peptide substrate. The kinase reaction is allowed to proceed for a fixed period, and the extent of substrate phosphorylation is quantified using techniques such as fluorescence polarization, luminescence-based kinase assays, or radiometric measurement. IC50 values are determined by fitting dose-response curves to the inhibition data. The compound is dissolved in DMSO and diluted in assay buffer to achieve the desired final concentrations, with DMSO concentration kept constant across all wells. Appropriate positive controls (known kinase inhibitors) and negative controls (DMSO vehicle) are included in each assay run.
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| Cell Assay |
The in vitro cellular assay for 5Z-7-Oxozeaenol is performed using cells that respond to inflammatory stimuli, such as macrophages or fibroblasts. Cells are cultured in appropriate medium and treated with varying concentrations of 5Z-7-Oxozeaenol or vehicle control (DMSO). Cells are then stimulated with IL-1β or TNF-α to activate TAK1 and downstream inflammatory signaling pathways. The phosphorylation status of TAK1, JNK, p38, IκB kinases, and NF-κB is assessed by Western blotting using phospho-specific antibodies. The production of COX-2 and other inflammatory mediators is measured by Western blotting, ELISA, or qRT-PCR. The inhibition of inflammatory signaling by 5Z-7-Oxozeaenol is quantified, and dose-response relationships are established.
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| Animal Protocol |
In vivo animal experiments with 5Z-7-Oxozeaenol are not extensively described in publicly available sources. Based on its in vitro activity, potential in vivo studies would likely use mouse models of inflammatory diseases such as collagen-induced arthritis, dextran sulfate sodium (DSS)-induced colitis, or lipopolysaccharide (LPS)-induced sepsis. 5Z-7-Oxozeaenol would be administered via intraperitoneal injection or oral gavage at various doses. Disease progression would be monitored using appropriate clinical scores, histological analysis, and measurement of inflammatory markers. At study endpoint, tissues would be harvested for analysis of target engagement, downstream signaling, and inflammatory mediators. The compound's efficacy would be evaluated by comparing disease severity in treated versus control groups.
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| ADME/Pharmacokinetics |
Detailed pharmacokinetic (PK) parameters for 5Z-7-Oxozeaenol are not extensively documented in publicly available sources. As a small-molecule kinase inhibitor with a molecular weight of 362.37, the compound is expected to have reasonable oral bioavailability. 5Z-7-Oxozeaenol has a chemical formula of C19H22O7. The compound is soluble in DMSO for formulation purposes. For in vivo administration, the compound would need to be formulated using appropriate vehicles to ensure adequate solubility and stability. The compound should be stored under conditions recommended by the manufacturer to maintain stability and prevent degradation. Detailed PK parameters including half-life, clearance, volume of distribution, and maximum concentration (Cmax) are not available from the current search results and would require consultation of the primary literature.
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| Toxicity/Toxicokinetics |
Comprehensive toxicological data for 5Z-7-Oxozeaenol are not extensively documented in publicly available sources. As a research-grade compound, 5Z-7-Oxozeaenol is intended for laboratory research purposes only and is not approved for human therapeutic use. Standard laboratory safety practices should be followed when handling this compound, including the use of appropriate personal protective equipment and working in a well-ventilated area. The compound should be stored according to the manufacturer's recommendations to maintain stability and prevent degradation. The compound is an irreversible kinase inhibitor that covalently modifies cysteine residues, and appropriate precautions should be taken to avoid exposure. Comprehensive toxicological profiling (e.g., LD50, maximum tolerated dose, organ-specific toxicity) is not available from the current search results and would require consultation of the primary literature or safety data sheets.
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| References |
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| Additional Infomation |
5Z-7-oxozeenol is a macrocyclic lactone compound, a 7-oxo derivative of zeenol (5Z stereoisomer). Isolated from fungi, it exhibits cytotoxic, antibacterial, and NF-κB inhibitory activities. It functions as a metabolite, antibacterial agent, antitumor agent, and NF-κB inhibitor. It is an aromatic ether, macrocyclic lactone, phenolic compound, secondary alcohol, and secondary α-hydroxy ketone. 5Z-7-oxozeenol has been reported in Curvularia lunata, and relevant data are available.
5Z-7-Oxozeaenol is a research compound developed for studying kinase signaling, inflammation, and cancer. The compound is a potent ATP-competitive irreversible inhibitor of TAK1, ERK2, MKK7, and MEK1. It blocks IL-1-induced activation of TAK1, JNK/p38 MAPK, IκB kinases, and NF-κB, resulting in inhibition of COX-2 production. The compound's irreversible binding mechanism ensures sustained inhibition of its target kinases. 5Z-7-Oxozeaenol is not currently in clinical trials nor approved for therapeutic use; it remains an investigational tool compound for preclinical research. The compound is available from various chemical suppliers for research purposes. Its utility lies in its ability to inhibit multiple kinases in inflammatory signaling pathways. |
| Molecular Formula |
C19H22O7
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|---|---|
| Molecular Weight |
362.37378
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| Exact Mass |
362.137
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| CAS # |
253863-19-3
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| PubChem CID |
9863776
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| Appearance |
White to off-white solid powder
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| LogP |
1.6
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
7
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
26
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| Complexity |
556
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| Defined Atom Stereocenter Count |
3
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| SMILES |
C[C@H]1C/C=C\C(=O)[C@H]([C@H](C/C=C/C2=C(C(=CC(=C2)OC)O)C(=O)O1)O)O
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| InChi Key |
NEQZWEXWOFPKOT-BYRRXHGESA-N
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| InChi Code |
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
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| Chemical Name |
(3S,5Z,8S,9S,11E)-3,4,9,10-Tetrahydro-8,9,16-trihydroxy-14-methoxy-3-methyl-1H-2-benzoxacyclotetradecin-1,7(8H)-dione
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| Synonyms |
FR-148083; L-783279; LL-Z 1640-2; FR148083; L783279; LL-Z 1640-2; 5Z-7-Oxozeaenol; 5Z 7 Oxozeaenol; 5Z7Oxozeaenol; 5-Z-7-Oxozeaenol; 5 Z 7 Oxozeaenol; 5Z7O; L-783279; 5 Z 7 O; L 783279; 5-Z-7-O; L783279; (5Z)-7-Oxozeaenol;
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~50 mg/mL (~137.98 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (6.90 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (6.90 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (6.90 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.7596 mL | 13.7981 mL | 27.5961 mL | |
| 5 mM | 0.5519 mL | 2.7596 mL | 5.5192 mL | |
| 10 mM | 0.2760 mL | 1.3798 mL | 2.7596 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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